Updated on 2024/07/17

写真a

 
NISHIYAMA,Yutaka
 
Organization
Faculty of Chemistry, Materials and Bioengineering Professor
Title
Professor
Contact information
メールアドレス
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Degree

  • Doctor of Engineering ( 1990.4 )

  • Master of Engineering ( 1985.3 )

Research Areas

  • Life Science / Bioorganic chemistry

  • Others / Others

Education

  • Osaka University   Graduate School, Division of Engineering   Applied Chemistry

    1985

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  • Osaka University   Faculty of Engineering   Applied Chemistry

    - 1983

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    Country: Japan

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  • Osaka University   Graduate School, Division of Engineering   Applied Chemistry

    1985

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    Country: Japan

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Research History

Professional Memberships

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Papers

  • Rhenium complex-catalyzed deoxygenation and silylation of alcohols with hydrosilane

    Yutaka Nishiyama, Shijie Xu, Yuuki Hanatani, Susumu Tsuda, Rui Umeda

    Tetrahedron Letters   99   2022.6

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    Publishing type:Research paper (scientific journal)  

    The reduction of benzylic, tertiary, and allylic alcohols with hydrosilane was efficiently catalyzed by the rhenium complex, such as ReBr(CO)5, to give the corresponding deoxygenarated products, alkanes, in moderate to good yields. In the case of aliphatic secondary alcohol, the alkane was formed along with the formation of dehydrated products. On the other hand, in the case of primary and cyclic alcohols, silylation of alcohols proceeded to form the corresponding silyl ethers.

    DOI: 10.1016/j.tetlet.2022.153839

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  • Selective synthesis of 1-halonaphthalenes by copper-catalyzed benzannulation

    Rui Umeda, Ryo Ueda, Taiki Tanaka, Akitsugu Hayashi, Masahiro Ikeshita, Shuichi Suzuki, Takeshi Naota, Yutaka Nishiyama

    Tetrahedron   79   131872 - 131872   2021.1

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    Publishing type:Research paper (scientific journal)   Publisher:Elsevier BV  

    DOI: 10.1016/j.tet.2020.131872

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  • Nitroselenation of carbon-carbon triple bond by PhSeSePh and NO/O2 or NO2 Reviewed

    Yutaka Nishiyama, M. Sumida, N. Sonoda

    Heteroatom Chemistry   2020, 10.1002/hc21480   2020

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  • Synthesis and Physics Properties of pai-Extended Molecules having p-Methylenequinone Unit Reviewed

    R. Umeda, M. Nakatsukasa, Yutaka Nishiyama

    Hetercycles   2020, 101, 318-327   2020

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  • Synthesis and physical properties of π-extended molecules having p-methylenequinone unit

    Rui Umeda, Masamichi Nakatsukasa, Yutaka Nishiyama

    Heterocycles   101 ( 1 )   318 - 327   2020

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    Language:English   Publishing type:Research paper (scientific journal)   Publisher:Japan Institute of Heterocyclic Chemistry  

    In this paper, we reported the facile synthesis of the π-extended molecules having p-methylenequinone unit from the aromatic ketones, such as fluorenone, xanthone, thioxanthone, dibenzosuberenone, and acridone, in few steps and the results of their physical properties.

    DOI: 10.3987/COM-19-S(F)12

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  • Facile and practical synthesis of pai-extended oxepins by benzannulation and intramolecular cyclization

    R. Umeda, Y. Shimizu, Y. Ida, M. Ikeshita, S. Suzuki, T. Naota, Yutaka Nishiyama

    Tetrahedron Lett.   2019, 60, 183-186   2019

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  • Synthesis of 1,2-Dihydroisoquinolines via Rhenium-catalyzed Tandem Cyclization and Nucleophilic Addition of 2-(1-Alkynyl)arylaldimines

    Rui Umeda, Tetsuya Ishida, Yota Nakagawa, Mitsuru Inoue, Tatsuo Yajima, Yutaka Nishiyama

    CHEMISTRY LETTERS   47 ( 6 )   753 - 755   2018.6

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    Language:English   Publishing type:Research paper (scientific journal)   Publisher:CHEMICAL SOC JAPAN  

    A synthetic method for 1,2-dihydroisoquinolines via the 6-endo-dig cyclization of 2-alkynylaldimines and nucleophilic addition has been developed. When the 2-alkynylaldimines were reacted with various nucleophiles such as nitromethane, dimethyl malonate, phenylacetylene, hydrosilane, allylstannane, and ketene silyl acetal in the presence of a rhenium catalyst, the corresponding 1,2-dihydroisoquinolines were obtained in moderate to good yields.

    DOI: 10.1246/cl.180200

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  • Rheniumx-Catalyzed alpha-alkylation of enal acetates with alcohols or ethers Reviewed

    R. Umeda, Y. Takahashi, T. Yamamoto, H. Iseki, I. Osaka, Yutaka Nishiyama

    J. Organomet. Chem.   2018, 877, 92-101   2018

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  • Synthesis of 1,2-Dihydroisoquinolines via Rhenium-catalyzed Tandem Cyclization and Nucleophilic Addition of 2-(1-Alkynyl)arylaldimines Reviewed

    R. Umeda, T. Ishida, Y. Nakagawa, M. Inoue, T. Yajima, Yutaka Nishiyama

    Chem. Lett.   2018, 47, 753-755   2018

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  • Rhenium Complex-catalyzed carbon-carbon formation of alcohols and organosilicon compounds Reviewed

    R. Umeda, T. Jikyo, K. Toda, I. Osaka, Yutaka Nishiyama

    Tetrahedron Lett.   2018, 59, 1121-1124   2018

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  • Rhenium complex-catalyzed Meinwald rearrangement reactions of oxiranes

    Rui Umeda, Masahito Muraki, Yuudai Nakamura, Tomoyuki Tanaka, Kyohei Kamiguchi, Yutaka Nishiyama

    TETRAHEDRON LETTERS   58 ( 24 )   2393 - 2395   2017.6

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    Language:English   Publishing type:Research paper (scientific journal)   Publisher:PERGAMON-ELSEVIER SCIENCE LTD  

    The Meinwald rearrangement reaction of oxiranes to the corresponding carbonyl compounds is efficiently catalyzed by the ReBr(CO)(5) complex. (C) 2017 Elsevier Ltd. All rights reserved.

    DOI: 10.1016/j.tetlet.2017.05.018

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  • Metal-free benzannulation to synthesis of 2,3-disubstituted naphthalenes: Reaction of 2-(Phenylethynyl)benzaldehyde and alkynes by Brønsted acid

    Rui Umeda, Naoki Ikeda, Masahiro Ikeshita, Keita Sumino, Sota Nishimura, Yutaka Nishiyama

    Bulletin of the Chemical Society of Japan   90 ( 2 )   213 - 215   2017

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    Language:English   Publishing type:Research paper (scientific journal)   Publisher:Chemical Society of Japan  

    Metal-free benzannulation reaction of 2-(phenylethynyl)- benzaldehyde and alkynes proceeded in the presence of Brønsted acid under microwave irradiation to give the 2,3- disubstituted naphthalenes.

    DOI: 10.1246/bcsj.20160308

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  • Synthesis and photophysical properties of 9,10-Bis(3-aryl-2-naphthyl)anthracenes

    Rui Umeda, Masahiro Kimura, Yoshito Tobe, Yutaka Nishiyama

    Bulletin of the Chemical Society of Japan   89 ( 1 )   110 - 112   2016

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    Language:English   Publishing type:Research paper (scientific journal)   Publisher:Chemical Society of Japan  

    The 9,10-bis(3-aryl-2-naphthyl)anthracenes 3 were prepared by the benzannulation reaction of 2-(phenylethynyl)benzaldehyde (1) and the corresponding 9,10-bis(arylethynyl)anthracenes 2 in the presence of Cu or Re catalyst and trichloroacetic acid. The photophysical properties of 3 in solutions were investigated.

    DOI: 10.1246/bcsj.20150341

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  • Synthesis of 4H-benz[de]anthracen-4-ones via 1,2-addition of metal acetylides to benzanthrone

    Rui Umeda, Teruaki Namba, Yuji Shimizu, Yutaka Nishiyama

    SYNTHETIC COMMUNICATIONS   46 ( 6 )   546 - 550   2016

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    Language:English   Publishing type:Research paper (scientific journal)   Publisher:TAYLOR & FRANCIS INC  

    Easy and facile syntheses of the 4H-benz[de]anthracen-4-one derivatives were achieved by the reaction of benzanthrone and lithium acetylides, followed by the treatment with silica gel in CHCl3.
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    DOI: 10.1080/00397911.2016.1154159

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  • Synthesis and Physical Properties of 6,12-Diarylindeno[1,2-b]fluorenes Reviewed

    R. Umeda, M. Nakatsukasa, M. Takehisa, T. Unzai, Y. Tobe, Y. Nishiyama

    Science and Technology Reports of Kansai University   2015, 57, 157-163.   2015.3

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  • Development of New Synthetic Reactions Using Lanthanum Metal Reviewed

    Rui Umeda, Yutaka Nishiyama

    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN   73 ( 1 )   57 - 68   2015.1

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    Language:Japanese   Publishing type:Research paper (scientific journal)   Publisher:SOC SYNTHETIC ORGANIC CHEM JPN  

    The utilization of lanthanoid metal salts and organolanthanoid compounds as synthestic reagents or catalysts in organic synthesis has been steadily interesting due to their unique chemical properties. Low-valent, trivalent, and tetravalent lanthanoid compounds have been widely used in organic reactions, however, the direct use of lanthanoid metal is still rare due to their low solubility in organic solvents or their instability under aerobic conditions.
    In this paper, we show the various organic reactions by the direct use of lanthanum metal as a reagent. Various unstable carbon species, such as alkyl radicals, o-quinodimethane, carbene, benzyne and alkylidene carbene, were easily generated by the reaction of organohalogen compounds with lanthanum metal. Carbonyl compounds were also reduced by lanthanum metal and the generated reducing species were widely used on the new carbon-carbon bond formations. The synthesis of organochalcogenides was successfully achieved by the reaction of dichalcogenides, alkyl halides, and lanthanum metal.

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  • Synthesis of isocoumarins: Rhenium complex-catalyzed cyclization of 2-ethynylbenzoic acids

    Rui Umeda, Shunya Yoshikawa, Kouji Yamashita, Yutaka Nishiyama

    Heterocycles   91 ( 11 )   2172 - 2179   2015

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    Language:English   Publishing type:Research paper (scientific journal)   Publisher:Japan Institute of Heterocyclic Chemistry  

    When 2-ethynylbenzoic acids were treated with a catalytic amount of a rhenium complex, such as ReCl(CO)5, 6-endo cyclization of 2-ethynylbenzoic acids proceeded with a high selectivity to give the corresponding isocoumarins in moderate to good yields.

    DOI: 10.3987/COM-15-13311

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  • A Novel Lanthanum Metal-Assisted Reaction of Diaryl Ketones and Electrophiles Reviewed

    R. Umeda, M. Ninomiya, T. Nishino, M. Kishida, S. Toiya, T. Saito, Y. Nishiyama, N. Sonoda

    Tetrahedron   2015, 71, 1287-1291.   2014.12

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  • 金属ランタンを用いる合成反応の開発 Reviewed

    梅田 塁, 西山 豊

    有機合成化学協会誌   2015, 73, 53-64.   2014.10

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  • Rhenium Complex-Catalyzed Coupling Reaction of Enol Acetates with Alcohols Reviewed

    R. Umeda, Y. Takahashi, Y. Nishiyama

    Tetrahedron Lett.   2014, 55, 61313-6116.   2014.9

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  • Synthesis of Multisubstituted 1H-Pyrrole: Selenium-Catalyzed Reaction of γ-Nitro Substituted Carbonyl Compounds and Carbon Monoxide Reviewed

    R. Umeda, T. Mashino, Y. Nishiyama

    Tetrahedron   2014, 70, 4395-4399.   2014.4

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  • Facile synthesis of 3, 3′-disubstituted 2, 2′-binaphthyls by transition-metal-catalyzed double benzannulation

    Rui Umeda, Hiromasa Tabata, Yoshito Tobe, Yutaka Nishiyama

    Chemistry Letters   43 ( 6 )   883 - 884   2014

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    Language:English   Publishing type:Research paper (scientific journal)   Publisher:Chemical Society of Japan  

    3, 3′-Disubstituted 2, 2′-binaphthyls were prepared by the Cuor Re-catalyzed double benzannulation reaction of 2-(phenylethynyl) benzaldehyde with various butadiynes in the presence of trichloroacetic acid, in moderate to good yields. Acceleration of the second benzannulation was clearly observed. © 2014 The Chemical Society of Japan.

    DOI: 10.1246/cl.140169

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  • Selective synthesis of quinolines and indoles: Sulfur-assisted or selenium-catalyzed reaction of β-(2-nitrophenyl)-α, β-unsaturated ketones with carbon monoxide

    Rui Umeda, Hiroshi Kouno, Takayuki Kitagawa, Tomohiro Okamoto, Keisuke Kawashima, Tsukasa Mashino, Yutaka Nishiyama

    Heteroatom Chemistry   25 ( 6 )   698 - 703   2014

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    Language:English   Publishing type:Research paper (scientific journal)   Publisher:Wiley-Blackwell  

    A simple and selective synthetic method of quinolines and indoles by the reaction of β- (2-nitrophenyl)-α,β-unsaturated ketones with carbon monoxide was developed. When β-(2-nitrophenyl)- α,β-unsaturated ketones were allowed to react with carbon monoxide and water in the presence of a stoichiometric amount of sulfur or a catalytic amount of selenium, the corresponding quinolines were produced in moderate-to-good yields. On the other hand, in the absence of water, the indoles were produced by the selenium-catalyzed reaction of the β-(2-nitrophenyl)- α,β-unsaturated ketones with carbon monoxide.

    DOI: 10.1002/hc.21189

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  • Synthesis of indoles: Sulfur-assisted reaction of 2-nitrostilbenes with carbon monoxide

    Rui Umeda, Yuuta Nishimoto, Tsukasa Mashino, Yutaka Nishiyama

    Heterocycles   87 ( 6 )   1241 - 1247   2013

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    When 2-nitrostilbenes were treated with carbon monoxide in the presence of elemental sulfur, the reductive N-heterocyclization of the 2-nitrostilbenes smoothly proceeded to give the corresponding indoles in moderate to good yields. © 2013 The Japan Institute of Heterocyclic Chemistry.

    DOI: 10.3987/COM-13-12708

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  • Selective Introducing of Aryl and Amino Groups: Reaction of Benzanthrone and Organometallic Reagents Reviewed

    R. Umeda, T. Namba, T. Yoshimura, M. Nakatsukasa, Y. Nishiyama

    Tetrahedron   2013, 69, 1526-1531.   2012.12

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  • Rhenium-Catalyzed Regioselective Synthesis of 1,2-Disubstituted Naphthalenes Reviewed

    R. Umeda, S. Nishi, A. Kojima, K. Kaiba, Y. Nishiyama

    Tetrahedron Lett.   2013, 54, 179-182.   2012.10

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  • Synthesis of dibenz[a,h]anthracenes by Pd-catalyzed intramolecular double-cyclization of (Z,Z)-p-styrylstilbenes

    Rui Umeda, Satoshi Miyake, Yutaka Nishiyama

    Chemistry Letters   41 ( 3 )   215 - 217   2012

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    Dibenz[a,h]anthracene (1a) and its dimethoxy derivatives 1b and 1c were synthesized by the Pd-catalyzed intramolecular double-cyclization of the corresponding (Z,Z)-p-styrylstilbene derivatives 25, which were readily prepared by the Wittig reaction. The optical properties of the dibenz[a,h]anthracenes 1a1c are also presented. © 2012 The Chemical Society of Japan.

    DOI: 10.1246/cl.2012.215

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  • pi-Sufficient heteroaromatic compounds fused naphthalimide unit as novel solvatochromic fluorophores

    Rui Umeda, Hiroaki Nishida, Motohiro Otono, Yutaka Nishiyama

    TETRAHEDRON LETTERS   52 ( 42 )   5494 - 5496   2011.10

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    Language:English   Publishing type:Research paper (scientific journal)   Publisher:PERGAMON-ELSEVIER SCIENCE LTD  

    The carbazoles 1 and dibenzofurans 2 having naphthalimide unit were synthesized by the cross coupling reaction of 4-bromonaphthalimide 3 with aniline and phenol derivatives followed by the intramolecular cyclization, respectively. The chromophores 1c and 2c substituted methoxy group exhibited the strong fluorescence solvatochromism. (C) 2011 Elsevier Ltd. All rights reserved.

    DOI: 10.1016/j.tetlet.2011.08.066

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  • Rhenium Complex-Catalyzed Acylative Cleavage of Ethers with Acyl Chlorides Reviewed

    R. Umeda, T. Nishimura (B), K. Kaiba (D), T. Tanaka (B), Y. Takahashi (D), Y. Nishiyama

    Tetrahedron   2011, 67, 7217-7221.   2011.6

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  • Rhenium-Catalyzed Benzannulation of o-Alkynylbenzaldehyde with Alkynes to Multiple 2,3-Disubstituted Naphthalenes Reviewed

    R. Umeda, K. Kaiba (D), S. Morishita (D), Y. Nishiyama

    ChemCatChem   2011, 3, 1743-1746.   2011.6

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  • Fritsch-Buttenberg-Wiechell rearrangement to alkynes from gem-dihaloalkenes with lanthanum metal Reviewed

    R. Umeda, T. Yuasa (D), N. Anahara (D), Y. Nishiyama

    J. Organomet. Chem.   2011, 696, 1916-1919.   2011.2

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  • Selenium-Catalyzed Reductive Cyclization and Carbocyclization of 2,2 '-Dinitrostilbenes with Carbon Monoxide: One-Shot Synthesis of Indolo[1,2-c]quinazolinones

    Rui Umeda, Shigeru Morishita, Yutaka Nishiyama

    HETEROATOM CHEMISTRY   22 ( 3-4 )   571 - 575   2011

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    Language:English   Publishing type:Research paper (scientific journal)   Publisher:WILEY  

    When 2,2'-dinitrostilbene derivatives were allowed to react with carbon monoxide in the presence of a catalytic amount of selenium, reductive cyclization and carbocyclization proceeded to give indolo[1,2-c]quinazolin-6(5H)-ones, containing both indole and cyclic urea units, in moderate yields. 2011 Wiley Periodicals, Inc. Heteroatom Chem 22:571-575, 2011; View this article online at wileyonlinelibraiy.com. DOI 10.1002/hc.20685

    DOI: 10.1002/hc.20685

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  • Utilization of Lanthanum Metal as a Reducing Agent in Organic Synthesis

    Yutaka Nishiyama

    RARE EARTHs   2011, 59, 19-27   2011

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  • Diphenyl diselenide-assisted α-phenylthiolation of carbonyl compounds with diphenyl disulfide

    Hiroaki Anbou, Rui Umeda, Yutaka Nishiyama

    Bulletin of the Chemical Society of Japan   84 ( 11 )   1248 - 1250   2011

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    For the cesium carbonate-catalyzed α-phenylthiolation of carbonyl compounds with diphenyl disulfide, the yields of the α-phenylthio carbonyl compounds were dramatically improved by the addition of a catalytic amount of diphenyl diselenide. © 2011 The Chemical Society of Japan.

    DOI: 10.1246/bcsj.20110127

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  • Rhenium complex as a useful catalyst for acylative cleavage of ethers

    Rui Umeda, Kenta Kaiba, Toshimasa Tanaka, Yuuki Takahashi, Takashi Nishimura, Yutaka Nishiyama

    Synlett   2010, 3089-3091. 2010, 3089- ( 20 )   3089 - 3091   2010

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    It was found that a rhenium complex such as ReBr(CO)5 acts as an efficient catalyst for the acylative cleavage of the carbon-oxygen bond of ethers with acyl chloride, giving the corresponding esters in moderate to good yields. © 2010 Georg Thieme Verlag Stuttgart, New York.

    DOI: 10.1055/s-0030-1259043

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  • Selenium-catalyzed deoxygenative reduction of aliphatic nitro compounds with carbon monoxide

    Yutaka Nishiyama, Sadatatsu Ikeda, Hiroaki Nishida, Rui Umeda

    Bulletin of the Chemical Society of Japan   83 ( 7 )   816 - 818   2010

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    A reduction method of aliphatic nitro compounds to oximes using carbon monoxide was developed. When aliphatic nitro compounds were treated with carbon monoxide in the presence of a selenium catalyst, the corresponding oximes were formed in moderate to good yields. © 2010 The Chemical Society of Japan.

    DOI: 10.1246/bcsj.20090347

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  • One-pot Synthetic Method of Unsymmetrical Diorganyl Selenides: Reaction of Diphenyl Diselenide with Alkyl Halides in the Presence of Lanthanum Metal

    NISHIYAMA,Yutaka

    67巻24号8696頁   2008.11

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  • 将来型電気エネルギー社会を支える「キャパシタ型蓄電システム」の開発プロジェクト

    西山 豊, 石川正司, 荒川隆一, 安田 陽

    技苑   126,pp. 65-73   2008

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  • Lanthanum metal-assisted cyclopropanation of alkenes with gem-dihaloalkanes

    Yutaka Nishiyama, Hana Tanimizu, Tsuyoshi Tomita

    TETRAHEDRON LETTERS   48 ( 36 )   6405 - 6407   2007.9

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    It was confirmed that lanthanurn metal was an efficient reagent for the reductive dehalogenation of gem-dihaloalkanes. When gem-dihaloalkanes were allowed to react with lanthanum metal in the presence of alkenes, cyclopropanation of the alkenes occurred under mild conditions giving the corresponding cyclopropanes in moderate to good yields. (C) 2007 Elsevier Ltd. All rights reserved.

    DOI: 10.1016/j.tetlet.2007.06.168

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  • Synthesis of 1,4-diketones: reaction of alpha-bromo ketones with tetrakis(dimethylamino)ethylene (TDAE)

    Yutaka Nishiyama, Akihiro Kobayashi

    TETRAHEDRON LETTERS   47 ( 31 )   5565 - 5567   2006.7

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    1,4-Diketones were prepared by the reaction of alpha-bromo ketones with tetrakis(dimethylamino)ethylene (TDAE) in moderate to good yields. Similarly, a-bromo esters were reductively coupled using TDAE to give the 1,4-diesters in moderate yields. (c) 2006 Elsevier Ltd. All rights reserved.

    DOI: 10.1016/j.tetlet.2006.05.141

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  • A facile method for the synthesis of 1,3-oxathiolan-2-ones by reaction of oxiranes, sulfur, and carbon monoxide

    Yutaka Nishiyama, Chisato Katahira, Noboru Sonoda

    TETRAHEDRON   62 ( 24 )   5803 - 5807   2006.6

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    Language:English   Publishing type:Research paper (scientific journal)   Publisher:PERGAMON-ELSEVIER SCIENCE LTD  

    A new method for the synthesis of 1,3-oxathiolan-2-ones has been developed. When oxiranes were allowed to react with sulfur in the presence of a catalytic amount of sodium hydride under pressurized carbon monoxide, the three-component coupling of oxiranes, sulfur, and carbon monoxide smoothly proceeded to give the 1,3-oxathiolan-2-ones in moderate to good yields. The reaction proceeded with a high regioselectivity and stereospecificity. For the reaction of oxiranes possessing an aromatic ring, the yields of the 1,3-oxathiolan-2-ones were lower than that of the oxiranes possessing no aromatic ring due to the formation of alkenes and thiiranes as byproducts. However, the product yields were improved by the addition of a catalytic amount of selenium. (c) 2006 Elsevier Ltd. All rights reserved.

    DOI: 10.1016/j.tet.2006.03.081

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  • A new method for the synthesis of 2-aryl-1H-benzimidazoles: Selenium-catalyzed reductive N-heterocyclization of benzylidene(2-nitroaryl)amines with carbon monoxide

    Y Nishiyama, M Fujimoto, N Sonoda

    SYNLETT   No. 1, 109-111 ( 1 )   109 - 111   2006.1

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    Language:English   Publishing type:Research paper (scientific journal)   Publisher:GEORG THIEME VERLAG KG  

    The treatment of benzylidene(2-nitroaryl)amines, prepared by the reaction of o-nitro aniline and benzaldehydes, with carbon monoxide in the presence of a catalytic amount of selenium under basic conditions, afforded 2-aryl-1H-benzimidazoles in moderate to good yields.

    DOI: 10.1055/s-2005-922771

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  • A new method for synthesis of S-aryl-O-alkyl thiolcarbonates: selenium-catalyzed reaction of alcohols with carbon monoxide and diaryl disulfides

    Y Nishiyama, K Maehira, J Nakase, N Sonoda

    TETRAHEDRON LETTERS   46 ( 43 )   7415 - 7417   2005.10

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    Language:English   Publishing type:Research paper (scientific journal)   Publisher:PERGAMON-ELSEVIER SCIENCE LTD  

    A unique catalytic ability of selenium has been developed. When alcohols were allowed to react with diaryl disulfides in the presence of a catalytic amount of selenium under a pressurized carbon monoxide, S-aryl-O-alkyl thiolcarbonates were obtained in moderate to good yields. (c) 2005 Elsevier Ltd. All rights reserved.

    DOI: 10.1016/j.tetlet.2005.08.108

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  • A facile method for the synthesis of thiocarbamates: Palladium-catalyzed reaction of disulfide, amine, and carbon monoxide

    Y Nishiyama, H Kawamatsu, N Sonoda

    JOURNAL OF ORGANIC CHEMISTRY   70 ( 7 )   2551 - 2554   2005.4

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    Language:English   Publishing type:Research paper (scientific journal)   Publisher:AMER CHEMICAL SOC  

    A new method for the synthesis of thiocarbamates has been developed. When dialkyl or diaryl disulfides were allowed to react with secondary amines and carbon monoxide in the presence of a catalytic amount of a palladium complex, the thiocarbamates were obtained in moderate to good yields. In contrast to that of secondary amines, in the reaction of a primary amine, no formation of thiocarbamate was confirmed, but urea was formed in good yield.

    DOI: 10.1021/jo048350h

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  • Utilization of phenyl trialkylstannyl selenide as a promising reagent for introduction of the phenylseleno group

    Y Nishiyama, N Sonoda

    MINI-REVIEWS IN ORGANIC CHEMISTRY   2 ( 2 )   147 - 155   2005.4

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    Language:English   Publishing type:Research paper (scientific journal)   Publisher:BENTHAM SCIENCE PUBL LTD  

    New synthetic methods of organoselenium compounds by the use of phenyl tributylstannyl selenide (PhSeSnBu3) (1), which is a stable selenium reagent in air and moisture, as a phenylselenated reagent have been developed. In the presence of palladium complex catalyst, the reaction of 1 with organohalogen compounds took place efficiently to give the corresponding organoselenium compounds in moderate to good yields. Furthermore, it was found that Lewis acid assisted the reaction of 1 with oxygen-containing compounds giving the corresponding organoselenium compounds.

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  • A new method for the synthesis of organotellurium compounds by the use of reductive cleavage of the tellurium-tellurium bond with lanthanum metal

    Y Nishiyama, M Okada, T Nishino, N Sonoda

    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN   78 ( 2 )   341 - 343   2005.2

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    Language:English   Publishing type:Research paper (scientific journal)   Publisher:CHEMICAL SOC JAPAN  

    It was confirmed that lanthanum metal is an efficient reagent for the reductive cleavage of the tellurium-tellurium bond of ditelluride. Alkyl phenyl tellurides were prepared by the reaction of diphenyl ditelluride with primary and secondary alkyl halides in the presence of lanthanum metal and a catalytic amount of iodine in moderate to good yields. The reaction was accelerated by the addition of HMPA. In addition, the reduction of ditelluride with lanthanum metal, followed by the addition of acyl or aroyl chlorides or alpha,beta-unsaturated ester, provided the Te-phenyl tellurol esters and the beta-phenyl telluro ester in moderate yields.

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  • Reductive debromination of 1,2-bis(bromomethyl)arenes using tetrakis(dimethylamino)ethylene (TDAE)

    Y Nishiyama, H Kawabata, A Kobayashi, T Nishino, N Sonoda

    TETRAHEDRON LETTERS   46 ( 5 )   867 - 869   2005.1

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    A new method for the reductive debromination of 1,2-bis(bromomethyl)arenes has been developed. The treatment of 1,2- bis(bromomethyl)benzene with tetrakis(dimethylamino)ethylene (TDAE) (1) in the presence of olefins gave 1,2,3,4-tetrahydronaphthalenes in moderate to good yields. (C) 2004 Elsevier Ltd. All rights reserved.

    DOI: 10.1016/j.tetlet.2004.11.114

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  • Rhenium complex-catalyzed allylation of aldehydes with allyltributylstannane

    Y Nishiyama, F Kakushou, N Sonoda

    TETRAHEDRON LETTERS   46 ( 5 )   787 - 789   2005.1

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    It was confirmed that the rhenium complex, ReBr(CO)(5), catalyzed the allylation of aldehydes with allyltributylstannane to give the corresponding homoallylic alcohols in moderate to good yields. Similarly, the reaction of aldehydes with enol silyl ether was efficiently promoted by the rhenium catalyst to afford the corresponding beta-hydroxy carbonyl compounds. (C) 2004 Elsevier Ltd. All rights reserved.

    DOI: 10.1016/j.tetlet.2004.12.022

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  • A new method for the synthesis of 1,3-oxathiolan-2-ones by the reaction of epoxides with sulfur and carbon monoxide

    Y Nishiyama, C Katahira, N Sonoda

    TETRAHEDRON LETTERS   45 ( 46 )   8539 - 8540   2004.11

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    The convenient method for the synthesis of 1,3-oxathiolan-2-ones by the reaction of epoxides with elemental sulfur and carbon monoxide in the presence of catalytic amount of sodium hydride has been developed. (C) 2004 Elsevier Ltd. All rights reserved.

    DOI: 10.1016/j.tetlet.2004.09.105

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  • A new synthetic method of 1,4-dihydro-2H-3,1-benzoxazin-2-ones: Selenium-catalyzed reductive carbonylation of aromatic nitro compounds with carbon monoxide

    Y Nishiyama, Y Naitoh, N Sonoda

    SYNLETT   5, 886-888 ( 5 )   886 - 888   2004.4

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    It was confirmed that selenium catalyzed the reaction of 2-nitrobenzyl alcohols with carbon monoxide to afford 1,4-dihydro-2H-3,1-benzoxazin-2-ones in good yields. Similarly, seven-membered cyclic carbamate was prepared by the reaction of 2-(2-nitrophenyl)ethanol with carbon monoxide.

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  • Synthesis and characterization of triphenylene-dione half-disc mesogens

    AJ Paraskos, Y Nishiyama, TM Swager

    MOLECULAR CRYSTALS AND LIQUID CRYSTALS   411   1405 - 1417   2004

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    Novel half-disc mesogens of general structure 6,7,10,11-tetrakis(alkoxy)triphenylene-1,4-dione were synthesized and their phases characterized by polarized microscopy, differential scanning calorimetry and X-ray diffraction. These compounds were found to form hexagonal columnar mesophases upon heating, despite their half-disc molecular shapes. X-ray diffraction suggests that within the mesophases a dimeric mesogenic subunit exists, driven by dipolar forces, in which the molecules are oriented antiparallel to one another. Such a dimer is approximately disc-shaped, and may explain the formation of columnar phases by these half-disc molecules.

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  • A facile method for synthesis of alkyl phenyl selenides. The reaction of diphenyl diselenide with oxygen-containing compounds using La/Me3SiCl/I-cat.(2)/(CuI)-Cu-cat. system

    T Nishino, Y Nishiyama, N Sonoda

    CHEMISTRY LETTERS   32 ( 10 )   918 - 919   2003.10

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    Alcohols, ethers, and esters were directly converted to the corresponding alkyl phenyl selenides by the reaction of diphenyl diselenide and the La/Me3SiCl/I-cat.(2)/(CUI)-C-cat.. It was suggested that alkyl phenyl selenides were formed by the S(H)2 type reaction of diphenyl diselenide with alkyl radicals generated from alcohols, ethers or esters.

    DOI: 10.1246/cl.2003.918

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  • A facile method for synthesis of alkyl phenyl selenides. The reaction of diphenyl diselenide with oxygen-containing compounds using La/Me3SiCl/I-cat.(2)/(CuI)-Cu-cat. system

    T Nishino, Y Nishiyama, N Sonoda

    CHEMISTRY LETTERS   32 ( 10 )   918 - 919   2003.10

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    Alcohols, ethers, and esters were directly converted to the corresponding alkyl phenyl selenides by the reaction of diphenyl diselenide and the La/Me3SiCl/I-cat.(2)/(CUI)-C-cat.. It was suggested that alkyl phenyl selenides were formed by the S(H)2 type reaction of diphenyl diselenide with alkyl radicals generated from alcohols, ethers or esters.

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  • Dehalogenation of o-Dihalogen Substituted Arenes and ┣T00210┫,┣T00210┫'-Dihalogen Substituted o-Xylenes with Lanthanum metal Reviewed

    NISHIYAMA Yutaka

    Tetrahedron   59巻34号6609頁   2003.8

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  • Phenyl tributylstannyl selenide as a promising reagent for introducion of the phenylseleno group

    Y Nishiyama, H Kawamatsu, S Funato, K Tokunaga, N Sonoda

    JOURNAL OF ORGANIC CHEMISTRY   68 ( 9 )   3599 - 3602   2003.5

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    A new synthetic method of organoselenium compounds has been developed. When phenyl tributylstannyl selenide (PhSeSnBu3) was allowed to react with acyl or aroyl chlorides in the presence of a catalytic amount of a palladium complex such as Pd(PPh3)(4), Se-phenyl selenol esters were obtained in moderate to good yields. Similarly, the palladium complex catalyzed the reaction of PhSeSnBu3 with alpha-halo carbonyl compounds to afford the corresponding alpha-phenyseleno carbonyl compounds in moderate yields.

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  • Deoxygenative dimerization of benzylic and allylic alcohols, and their ethers and esters using lanthanum metal and chlorotrimethylsilane in the presence of a catalytic amount of iodine and copper(I) iodide

    T Nishino, Y Nishiyama, N Sonoda

    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN   76 ( 3 )   635 - 641   2003.3

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    Benzylic and allylic alcohols were deoxygenatively dimerized by a treatment with lanthanum metal and chlorotrimethylsilane in the presence of a catalytic amount of iodine, giving the corresponding coupling products, alkanes, in moderate-to-good yields. This dimerization reaction was dramatically accelerated by the addition of a catalytic amount of copper(I) iodide. Similarly, ethers and esters were deoxygenatively dimerized by La/Me3SiCl/I-cat.(2)/(CuI)-Cu-cat. system in the presence of a catalytic amount of H2O.

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  • One-pot Synthetic Method of Unsymmetrical Diorganyl Selenides: Reaction of Diphenyl Diselenide with Alkyl Halides in the Presence of Lanthanum Metal Reviewed

    NISHIYAMA Yutaka

    The Journal of Organic Chemistry   67巻24号8696頁   2002.11

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  • Reaction of carbonyl compounds with trialkylsilyl phenylselenide and tributylstannyl hydride under radical conditions

    Y Nishiyama, H Kajimoto, K Kotani, T Nishida, N Sonoda

    JOURNAL OF ORGANIC CHEMISTRY   67 ( 16 )   5696 - 5700   2002.8

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    A novel method for the hydrosilylation of carbonyl compounds has been developed. When carbonyl compounds were allowed to react with trimethylsilyl phenylselenide and tributylstannyl hydride in the presence of a catalytic amount of AIBN as the radical initiator, hydrosilylation of the carbonyl compounds efficiently proceeded to give the corresponding silyl ethers in moderate to good yields. In the absence of carbonyl compounds, the triethylsilyl hydride was obtained by the reaction of PhSeSiEt3 with Bu3SnH. Although the tributylgermyl phenylselenide instead of PhSeSiMe3 was treated with tributylstannyl hydride in the presence of a benzaldehyde under radical conditions, hydrogermylated product was not obtained and tributylgermyl hydride was mainly formed.

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  • Reaction of 1,2-dihalogen substituted arenes with lanthanum metal: a new generation method of benzyne

    H Kawabata, T Nishino, Y Nishiyama, N Sonoda

    TETRAHEDRON LETTERS   43 ( 28 )   4911 - 4913   2002.7

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    A new generation method of benzytle has been developed. When 1.2-dihalogen substituted arenes were allowed to react with lanthanum metal in the presence of dienes. Diels-Alder products between benzyne and dienes were formed in moderate to good yields. (C) 2002 Elsevier Science Ltd. All rights reserved.

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  • Lanthanum metal-assisted deoxygenative coupling of alcohols

    T Nishino, Y Nishiyama, N Sonoda

    TETRAHEDRON LETTERS   43 ( 20 )   3689 - 3691   2002.5

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    It was found that the deoxygenative coupling of alcohols efficiently proceeded by treatment with lanthanum metal and chlorotrimethylsilane in the presence of a catalytic amount of iodine. This coupling reaction was accelerated by the addition of a catalytic amount of copper(I) iodide. (C) 2002 Elsevier Science Ltd. All rights reserved.

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  • Synthesis of 3,4-dihydroquinazolin-4-one: selenium-catalyzed reductive N-heterocyclization of N-(2-nitrobenzoyl)amides with carbon monoxide

    Y Nishiyama, M Hirose, W Kitagaito, N Sonoda

    TETRAHEDRON LETTERS   43 ( 10 )   1855 - 1858   2002.3

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    A catalytic synthetic method of 3,4-dihydroquinazolin-4-ones has been developed. When N-(2-nitrobenzoyl)amides were treated with carbon monoxide in the presence of a catalytic amount of selenium, reductive N-heterocyclization of N-(2-nitrobenzoyl)amide efficiently proceeded to give the corresponding 3,4-dihydroquinazolin-4-ones in moderate to good yields. (C) 2002 Elsevier Science Ltd. All rights reserved.

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  • Tributylstannyl radical-catalyzed reaction of 1,2,3-selenadiazoles with olefins or dienes

    Y Nishiyama, Y Hada, M Anjiki, K Miyake, S Hanita, N Sonoda

    JOURNAL OF ORGANIC CHEMISTRY   67 ( 5 )   1520 - 1525   2002.3

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    It was found that the reaction of 1,2,3-selenadiazoles derived from cyclic ketones with olefins or dienes was markedly promoted by a catalytic amount of tributylstannyl radical, which was generated in situ from tributylstannyl hydride or allyltributylstannane and AIBN, to give the corresponding dihydroselenophenes in moderate to good yields. In contrast, when 1, 2,3 -selenadiazoles prepared from linear and aromatic ketones were used as substrates, the same reaction did not take place, and alkynes were formed as the sole product.

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  • Reduction of organic halides with lanthanum metal: A novel generation method of alkyl radicals

    T Nishino, T Watanabe, M Okada, Y Nishiyama, N Sonoda

    JOURNAL OF ORGANIC CHEMISTRY   67 ( 3 )   966 - 969   2002.2

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    Results of the reaction of alkyl halides with lanthanum metal have been shown. The reduction of alkyl iodide with 1/3 equiv of lanthanum metal efficiently proceeded to give the corresponding reductive dimerized products along with the formation of reduction and dehydroiodination products. In the case of alkyl bromides and chlorides, the reaction did not proceed under the same reaction conditions as that of alkyl iodides; however, the reaction was dramatically promoted by the addition of a catalytic amount of iodine. A reaction pathway including alkyl radicals was suggested.

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  • Synthesis of selenol esters: palladium-catalyzed coupling of phenyl tributylstannyl selenide with aryl iodides and carbon monoxide

    Y Nishiyama, K Tokunaga, H Kawamatsu, N Sonoda

    TETRAHEDRON LETTERS   43 ( 8 )   1507 - 1509   2002.2

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    It was found that palladium complex catalyzed three-component coupling of phenyl tributylstannyl selenide with aryl iodides and carbon monoxide to afford the corresponding, selenol esters in moderate to good yields. (C) 2002 Elsevier Science Ltd. All rights reserved.

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  • Reductive dimerization and reduction of imines using lanthanum metal

    T Nishino, Y Nishiyama, N Sonoda

    HETEROATOM CHEMISTRY   13 ( 2 )   131 - 135   2002

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    The treatment of N-benzylideneaniline (1a) with a half-equivalent of lanthanum metal and a catalytic amount of iodine gave the reductive dimerization product of 1a, a vic-diamine, in good yield. Various vic-diamines were synthesized from aldimines in this manner in moderate to good yields. Our findings suggest that electrons of a zero-valent lanthanum metal were efficiently utilized in this reductive dimerization. In the reaction of ketimines, however, a similar reductive dimerization did not take place, and the corresponding amines were formed as the sole products. (C) 2002 Wiley Periodicals, Inc.

    DOI: 10.1002/hc.10007

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  • Hydrosilylation of carbonyl compounds using a PhSeSiMe3/Bu3SnH/AIBN system

    Y Nishiyama, H Kajimoto, K Kotani, N Sonoda

    ORGANIC LETTERS   3 ( 20 )   3087 - 3089   2001.10

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    When carbonyl compounds were allowed to react with phenyl trimethylsilyl selenide and tributylstannyl hydride in the presence of a catalytic amount of AIBN as a radical initiator, the hydrosilylation of the carbonyl compounds efficiently proceeded to give the corresponding silyl ethers in moderate to good yields.

    DOI: 10.1021/ol0162567

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  • Rhenium complexes-catalyzed alkylation of arenes with alkyl halides

    Y Nishiyama, F Kakushou, N Sonoda

    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN   73 ( 12 )   2779 - 2782   2000.12

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    Rhenium complexes have been shown to catalyze the alkylation of arenes with alkyl halides. When arenes were reacted with an alkyl chloride in the presence of a catalytic amount of rhenium complexes, such as bromopenta-carbonylrhenium(I) [ReBr(CO)(5)], tricarbonylcyclopentadienylrhenium(I) [Re(C5H5)(CO)(3)] and decacarbonyldirhenium [Re-2(CO)(10)], alkylation of the arenes proceeded under mild conditions to give a mixture of mono- and dialkyl substituted arenes in moderate-to-good yields.

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  • The reaction of 1,2,3-selenadiazole with olefins

    Y Nishiyama, Y Hada, K Iwase, N Sonoda

    JOURNAL OF ORGANOMETALLIC CHEMISTRY   611 ( 1-2 )   488 - 493   2000.10

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    When 1,2,3-selenadiazoles synthesized from cyclic ketones were treated with an excess amount of olefins at 130 degrees C, the addition of a vinyl radical, which was generated in situ by the denitrogenation of 1,2,3-selenadiazoles, to a carbon-carbon double bond followed by intramolecular cyclization proceeded efficiently giving the corresponding dihydroselenophenenes in moderate to good yields along with the formation of the corresponding 1,4-diselenins and selenophenes as by-products. In this reaction, the number of carbon atoms on the cyclic ring of the ketones used as the starting materials in the synthesis of the 1,2,3-selenadiazoles plays an important role in the selectivity of the products. In contrast to the reaction of the 1,2,3-selenadiazoles prepared from the cyclic ketones, in the reaction of 1,2,3-selenadiazoles derived from aromatic and linear ketones, the dihydroselenophenene and 1,4-diselenins derivatives were not obtained and the corresponding alkynes were formed as the sole product. (C) 2000 Published by Elsevier Science S.A. All rights reserved.

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  • Development of New Synthetic Reactions Using Samarium Compounds as Catalysts

    NISHIYAMA Yutaka, SAKAGUCHI Satoshi, ISHII Yasutaka

    J. Synth. Org. Chem. Jpn.   58 ( 2 )   129 - 137   2000.2

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    The utilization of lanthanide metal salts and organolanthanide compounds in organic synthesis has been attracted considerable attention, however, there have been a limited number of studies on the synthetic reactions using divalent samarium compounds such as SmI<SUB>2</SUB> and Cp<SUP>*</SUP><SUB>2</SUB>Sm (thf) <SUB>2</SUB> as catalysts or catalyst precursors. We report here several synthetic reactions by the use of samarium complexes (II), namely SmI<SUB>2</SUB> and Cp<SUP>*</SUP><SUB>2</SUB>Sm (thf) <SUB>2</SUB>, as catalysts : (i) coupling reaction of vinyl esters with aldehydes, (ii) acylation of alcohols and amines with vinyl esters, (iii) acylation of tertiary alcohols with vinyl esters in the presence of a catalytic amount of oxime ester, (iv) synthesis of 1, 3-diol monoesters by the trimerization of aldehydes, (v) aldol type condensation of imines, and (vi) one-pot synthesis of pyrroles by the reaction of amines, aldehydes, and nitroalkanes.

    DOI: 10.5059/yukigoseikyokaishi.58.129

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  • Reductive coupling of carbonyl compounds using lanthanum metal

    T Nishino, Y Nishiyama, N Sonoda

    HETEROATOM CHEMISTRY   11 ( 1 )   81 - 85   2000

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    We found that lanthanum metal was an excellent agent for the reduction of carbonyl compounds in the presence of a catalytic amount of iodine. When carbonyl compounds were treated with lanthanum metal in the presence of a catalytic amount of iodine, the reductive coupling of the carbonyl compounds proceeded efficiently to afford the corresponding vic-diols in moderate to good yields. (C) 2000 John Wiley & Sons, Inc.

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  • New synthetic method of diorganyl selenides: Palladium-catalyzed reaction of PhSeSnBu3 with aryl and alkyl halides

    Y Nishiyama, K Tokunaga, N Sonoda

    ORGANIC LETTERS   1 ( 11 )   1725 - 1727   1999.12

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    Palladium complexes such as Pd(PPh3)(4) catalyzed the reaction of phenyl tributylstannyl selenide (PhSeSnBu3) with aryl and alkyl halides, giving the corresponding diaryl and alkylaryl selenides in moderate to good yields.

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  • Catalytic use of organostannyl radical: The reaction of 1,2,3-selenadiazole with olefins in the presence of a catalytic amount of tributyltin hydride

    Y Nishiyama, Y Hada, M Anjiki, S Hanita, N Sonoda

    TETRAHEDRON LETTERS   40 ( 34 )   6293 - 6296   1999.8

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    When 1,2,3-selenadiazoles were treated with an excess amount of olefins in the presence of a catalytic amount of Bu3SnH and AIBN, the addition of a vinyl radical, which was generated in situ by the denitrogenation of 1,2,3-selenadiazoles, to the carbon-carbon double bond followed by intramolecular cyclization proceeded efficiently to afford the corresponding dihydroselenophenes in moderate to good yields. (C) 1999 Elsevier Science Ltd. All rights reserved.

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  • Synthesis of indoles: Selenium-catalyzed reductive N-heterocyclization of 2-nitrostyrenes with carbon monoxide

    Y Nishiyama, R Maema, K Ohno, M Hirose, N Sonoda

    TETRAHEDRON LETTERS   40 ( 31 )   5717 - 5720   1999.7

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    Reductive N-heterocyclization of 2-nitrostyrenes with carbon monoxide in the presence of a catalytic amount of selenium proceeded efficiently to afford the corresponding indoles in moderate to good yields. (C) 1999 Elsevier Science Ltd. All rights reserved.

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  • Regioselective alkylation of 1-alkoxy-3-phenylseleno-1-alkenes

    Y Nishiyama, Y Kishimoto, K Itoh, N Sonoda

    SYNLETT   5号611頁 ( 5 )   611 - 613   1999.5

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    The addition of various electrophiles to phenylseleno-substituted allyllithium, which was generated irt situ by the reaction of 1 -alkoxy-3-phenylseleno-1-alkene with LDA, gave the corresponding a-addition products in moderate to good yields with high regioselectivity.

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  • Selective synthesis of 1-alkoxy-3-phenylseleno-1-alkenes and 3-phenylselenoalkanals by the reaction of diisobutylaluminum phenylselenolate with alpha,beta-unsaturated acetals

    Y Nishiyama, T Asano, Y Kishimoto, K Itoh, Y Ishii

    TETRAHEDRON LETTERS   39 ( 47 )   8685 - 8686   1998.11

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    The reaction of alpha,beta-unsaturated acetals with diisobutylaluminum phenylselenolate followed by treatment with H2O affords the corresponding 1-alkoxy-3-phenylseleno-1-alkenes in good yields. When aq. HCl instead of H2O was employed in the workup, 3-phenylselenoalkanals were formed in good yields. (C) 1998 Elsevier Science Ltd. All rights reserved.

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  • Stereoselective reductive coupling of carbonyl compounds by a Sm/Et2AlI system

    Y Nishiyama, E Shinomiya, S Kimura, K Itoh, N Sonoda

    TETRAHEDRON LETTERS   39 ( 22 )   3705 - 3708   1998.5

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    A new method for generation of the samarium (II) species by the reaction of samarium metal with diethylaluminium iodide (Et2AlI) under mild conditions has been developed. Divalent samarium species generated in situ from a Sm/Et2AlI system caused the reductive coupling of aromatic ketones with moderate stereoselectivity to afford corresponding dl-vic-diols in moderate yields. (C) 1998 Elsevier Science Ltd. All rights reserved.

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  • Activation of Sn-Se bond: Regioselective ring opening reaction of epoxides with tributylstannyl phenylselenolate in the presence of a Lewis acid

    Y Nishiyama, H Ohashi, K Itoh, N Sonoda

    CHEMISTRY LETTERS   2巻159頁 ( 2 )   159 - 160   1998

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    When tributylstannyl phenylselenolate (Bu3SnSePh) was allowed to react with epoxides in the presence of BF3 . OEt2 as a Lewis acid, the ring opening reaction of epoxides proceeded with complete regioselectivity to afford the beta-hydroxy phenylselenides in moderate to good yields.

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  • Stereoselective synthesis of 2,2,5-trisubstituted tetrahydrofurans via the Lewis acid-assisted reaction of cyclic hemiketals with nucleophiles

    Y Nishiyama, T Katoh, K Deguchi, Y Morimoto, K Itoh

    JOURNAL OF ORGANIC CHEMISTRY   62 ( 26 )   9339 - 9341   1997.12

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  • Stereoselective reduction of beta-hydroxy ketones with aldehydes via Tishchenko reactions catalyzed by zirconocene complexes

    Y Umekawa, S Sakaguchi, Y Nishiyama, Y Ishii

    JOURNAL OF ORGANIC CHEMISTRY   62 ( 10 )   3409 - 3412   1997.5

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  • Stereoselective synthesis of trans-2,5-disubstituted tetrahydrofurans via the Lewis acid mediated reduction of cyclic hemiketals with triphenylsilane

    Y Nishiyama, T Tujino, T Yamano, M Hayashishita, K Itoh

    CHEMISTRY LETTERS   2号165頁 ( 2 )   165 - 166   1997

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    An efficient method for the synthesis of trans-2,5-disubstituted tetrahydrofuran derivatives has been developed. Dithioacetal-functionalized cyclic hemiketals are reduced by triphenylsilane (Ph(3)SiH) in the presence of TiCl4 to afford the corresponding trans-2,5-disubstituted tetrahydrofuran derivatives in good yield and high stereoselectivity. Asymmetrical synthesis of (2S,5S) disubstituted tetrahydrofuran was also achieved by using this reduction method.

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  • Molybdovanadophosphate (NPMoV)/hydroquinone/O-2 system as an efficient reoxidation system in palladium-catalyzed oxidation of alkenes

    T Yokota, S Fujibayashi, Y Nishiyama, S Sakaguchi, Y Ishii

    JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL   114 ( 1-3 )   113 - 122   1996.12

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    Molybdovanadophosphate (NPMoV)/hydroquinone/O-2 system was found to be an efficient reoxidation system in palladium-catalyzed oxidations of alkenes and related compounds. Thus, acetoxylations of cycloalkenes utilizing molecular oxygen as the final oxidant were cleanly performed using the multicatalytic system consisting of Pd(OAc)(2)/hydroquinone/NPMoV to form 3-acetoxy-1-cycloalkenes in good yields. For example, cyclopentene and cyclohexene were converted into the corresponding allylic acetates in almost quantitative yields. Omitting hydroquinone from the catalytic system led to low yields of the acetates. Acetoxylation of cyclooctene was satisfactorily achieved by replacing hydroquinone of the multicatalytic system by chlorohydroquinone. Molybdovanadophosphates, which catalyze the smooth dehydrogenation of hydroquinone to benzoquinone with dioxygen, were found to rapidly promote the present Pd(II)-catalyzed acetoxylation of cycloalkenes. By the use of a mixed solvent of ethanol and water under these conditions, Wacker type oxidations of cyclohexene and styrene were accomplished in fair to good yields. Monosubstituted alkenes such as ethyl acrylate and acrylonitrile underwent the acetalization by the present catalytic system to give the corresponding acetals in quantitative yields.

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  • Aldol type condensation of imines catalyzed by samarium complexes

    H Shiraishi, Y Kawasaki, S Sakaguchi, Y Nishiyama, Y Ishii

    TETRAHEDRON LETTERS   37 ( 40 )   7291 - 7294   1996.9

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    Aldol type condensation of imines has first been achieved via a catalytic process using samarium diiodide (SmI2) at room temperature to form alpha,beta-unsaturated imines in good yields. The condensation was markedly facilitated by the presence of formates or aldehydes which promote the elimination of amines from aldol adducts. It was found that the 1:2 reaction of amines with aldehydes under the influence of SmI2 also led to alpha,beta-unsaturated imines in satisfactory yields. Copyright (C) 1996 Elsevier Science Ltd

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  • Selective oxidation of monoterpenes with hydrogen peroxide catalyzed by peroxotungstophosphate (PCWP)

    S Sakaguchi, Y Nishiyama, Y Ishii

    JOURNAL OF ORGANIC CHEMISTRY   61 ( 16 )   5307 - 5311   1996.8

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    Catalytic epoxidation of monoterpenes with aqueous hydrogen peroxide catalyzed by peroxotung-stophosphate (PCWP) under biphase conditions using chloroform as the solvent was examined. A variety of terpenes was oxidized to the corresponding monoepoxides or diepoxides in good yields under mild conditions. For example, limonene (1) was converted into limonene oxide (la) in which the cyclohexene double bond was selectively epoxidized in almost quantitative yield. The oxidation of gamma-terpinene (2) with 2.2 equiv of 35% H2O2 took place with high stereoselectivity to give cis-diepoxide 2c. In terpenes bearing electron-withdrawing groups such as neryl acetate (3), geranyl acetate (4), citral (5), and geranyl nitrile (6), the double bonds remote from the substituents were epoxidized in preference to the others. The epoxidation of linalool (9) by the present catalyst-oxidant system produced the cyclic products, hydroxy furan 9a and hydroxy pyran 9b, rather than epoxide. tert-Butyl alcohol was successfully employed as the solvent by treating a hydrogen peroxide solution of tert-butyl alcohol with MgSO4 prior to use. The regioselectivities in the epoxidation of monoterpenes can be favorably explained from the electron densities of the double bonds which were estimated using the CAChe system.

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  • An efficient aerobic oxidation of various organic compounds catalyzed by mixed addenda heteropolyoxometalates containing molybdenum and vanadium

    S Fujibayashi, K Nakayama, M Hamamoto, S Sakaguchi, Y Nishiyama, Y Ishii

    JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL   110 ( 2 )   105 - 117   1996.8

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    Various organic compounds were oxidized by molecular oxygen in the presence of a catalytic amount of mixed-addenda heteropolyoxometalates containing molybdenum and vanadium. The catalytic activity of the molybdovanadophosphate was found to be greatly enhanced by supporting on charcoal. The supported catalyst has high catalytic activity for oxidative dehydrogenation of benzylic and allylic alcohols to the corresponding aldehydes and ketones (46-92%), nevertheless, the non-supported catalyst was inactive for the same oxidations under these conditions. 2,3,6-Trimethylphenol was selectively oxidized to trimethyl-p-benzoquinone, which is a precursor of vitamin E, in the presence of a catalytic amount of molybdovanadophosphate. In addition, the aerobic oxidation of amines, alkyl-substituted phenols, and alkanes were also examined.

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  • Alkane oxidation with molecular oxygen using a new efficient catalytic system: N-hydroxyphthalimide (NHPI) combined with Co(acac)(n) (n=2 or 3)

    Y Ishii, T Iwahama, S Sakaguchi, K Nakayama, Y Nishiyama

    JOURNAL OF ORGANIC CHEMISTRY   61 ( 14 )   4520 - 4526   1996.7

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    A novel class of catalysts for alkane oxidation with molecular oxygen was examined. N-Hydroxyphthalimide (NHPI) combined with Co(acac)(n) (n = 2 or 3) was found to be an efficient catalytic system for the aerobic oxidation of cycloalkanes and alkylbenzenes under mild conditions. Cycloalkanes were successfully oxidized with molecular oxygen in the presence of a catalytic amount of NHPI and Co(acac)(2) in acetic acid at 100 degrees C to give the corresponding cycloalkanones and dicarboxylic acids. Alkylbenzenes mere also oxidized with dioxygen using this catalytic system. For example, toluene was converted into benzoic acid in excellent yield under these conditions. Ethyl- and butylbenzenes were selectively oxidized at their alpha-positions to form the corresponding ketones, acetophenone, and 1-phenyl-1-butanone, respectively, in good yields. A key intermediate in this oxidation is believed to be the phthalimide N-oxyl radical generated from NHPI and molecular oxygen using a Co(II) species. The isotope effect (k(H)/k(D)) in the oxidation of ethylbenzene and ethylbenzene-d(10) with dioxygen using NHPI/Co(acac)(2) was 3.8.

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  • Acylation of alcohols and amines with vinyl acetates catalyzed by Cp*Sm-2(thf)(2)

    Y Ishii, M Takeno, Y Kawasaki, A Muromachi, Y Nishiyama, S Sakaguchi

    JOURNAL OF ORGANIC CHEMISTRY   61 ( 9 )   3088 - 3092   1996.5

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    Cp*Sm-2(thf)(2) was found to be an efficient catalyst for the acylation of alcohols and amines with esters under mild conditions. In the present acylation, vinyl and isopropenyl acetates served as good acylating agents. Thus, a variety of alcohols and amines underwent acylation with vinyl and isopropenyl acetates in the presence of Cp*Sm-2(thf)(2) to give the corresponding esters and amides in good to excellent yields. This catalytic acylation of alcohols and amines offers an additional useful method by the use of various esters, instead of acid anhydrides and acid chlorides, as acylating agents under very mild conditions.

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  • Reduction of Aromatic Nitro Compounds by the Sm/RnSiCl4-n/NaI System:Control of ReducingAbility of Low Valent Samarium Species Reviewed

    NISHIYAMA Yutaka

    Technology Reports of Kansai University.   38号113頁   1996

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  • Oxidation of Organic Substrates with Molecular Oxygen Catalyzed by Vanadomolybdophosphate(NPV6Mo6)Combined with N-Hydroxyphthalimide(NHPI) Reviewed

    NISHIYAMA Yutaka

    Technology Reports of Kansai University   38号123頁   1996

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  • OXIDATIVE ESTERIFICATION OF PRIMARY ALCOHOLS BY NABRO3/NAHSO3 REAGENT IN AQUEOUS-MEDIUM

    K TAKASE, H MASUDA, O KAI, Y NISHIYAMA, S SAKAGUCHI, Y ISHII

    CHEMISTRY LETTERS   10号871頁 ( 10 )   871 - 872   1995.10

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    NaBrO3 combined with NaHSO3 was found to be an efficent reagent for the oxidative esterification of primary alcohols. Thus, a variety of esters was prepared from primary alcohols, aldehydes, and acetals in aqueous medium under mild conditions. Treatment of alpha,omega-diols with NaBrO3/NaHSO3 reagent afforded the corresponding lactones and/or dicarboxylic acids in fair yields.

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  • AEROBIC OXIDATION OF ALCOHOLS TO CARBONYL-COMPOUNDS CATALYZED BY N-HYDROXYPHTHALIMIDE (NHPI) COMBINED WITH CO(ACAC)(3)

    T IWAHAMA, S SAKAGUCHI, Y NISHIYAMA, Y ISHII

    TETRAHEDRON LETTERS   36 ( 38 )   6923 - 6926   1995.9

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    Aerobic oxidation of various alcohols has been accomplished by using a new catalytic system, N-hydroxyphthalimide (NHPI) combined with Co(acac)(3). The oxidation of alcohols by NHPI was found to be markedly enhanced by adding a slight amount of Co(acac)(3) (0.05 equiv. to NHPI). Thus, secondary alcohols and vic-diols which are difficult to be oxidized by NHPI alone were smoothly oxidized with molecular oxygen (1 atm) to the corresponding carbonyl compounds under relatively mild conditions (65 similar to 75 degrees C).

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  • A NEW COUPLING REACTION OF VINYL ESTERS WITH ALDEHYDES CATALYZED BY ORGANOSAMARIUM COMPOUNDS

    M TAKENO, S KIKUCHI, KI MORITA, Y NISHIYAMA, Y ISHII

    JOURNAL OF ORGANIC CHEMISTRY   60 ( 16 )   4974 - 4975   1995.8

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  • A NOVEL CATALYSIS OF N-HYDROXYPHTHALIMIDE IN THE OXIDATION OF ORGANIC SUBSTRATES BY MOLECULAR-OXYGEN

    Y ISHII, K NAKAYAMA, M TAKENO, S SAKAGUCHI, T IWAHAMA, Y NISHIYAMA

    JOURNAL OF ORGANIC CHEMISTRY   60 ( 13 )   3934 - 3935   1995.6

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  • A DIRECT CONVERSION OF VIC-DIOLS INTO 1,2-DIKETONES WITH AQUEOUS HYDROGEN-PEROXIDE CATALYZED BY PEROXOTUNGSTOPHOSPHATE (PCWP)

    T IWAHAMA, S SAKAGUCHI, Y NISHIYAMA, Y ISHII

    TETRAHEDRON LETTERS   36 ( 9 )   1523 - 1526   1995.2

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    alpha-Hydroxy ketones and vic-diols were successfully oxidized to the corresponding diketones with agueous hydrogen peroxide in the presence of a catalytic amount of peroxotungstophosphate (PCWP). This method provides a straightforward route of 1,2-diketones which are difficult to prepare by conventional oxidation of vic-diols.

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  • OXIDATION OF ALLENES AND ALKYNES WITH HYDROGEN-PEROXIDE CATALYZED BY CETYLPYRIDINIUM PEROXOTUNGSTOPHOSPHATE (PCWP)

    S SAKAGUCHI, S WATASE, Y KATAYAMA, Y SAKATA, Y NISHIYAMA, Y ISHII

    JOURNAL OF ORGANIC CHEMISTRY   59 ( 19 )   5681 - 5686   1994.9

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    The oxidation of allenes and alkynes with hydrogen peroxide catalyzed by peroxotungstophosphate (PCWP) was examined. A variety of allenes were first converted into the corresponding alpha-ethoxy ketones upon treatment with 35% H2O2 under the influence of PCWP in a mixed solvent consisting of ethanol and dichloromethane. When the reaction was carried out using tert-butyl alcohol as a solvent, approximately a 1:1 regioisomeric mixture of alpha-hydroxy ketones was obtained along with a small amount of alpha-tert-butoxy ketone. Oxidation of internal alkynes such as 4-octyne by the PCWP-H2O2 system under phase-transfer conditions using chloroform produced alpha,beta-epoxy ketones in good yields. The same reaction in a mixed solvent of ethanol and chloroform gave alpha,beta-unsaturated ketones rather than alpha,beta-epoxy ketones. Plausible reaction paths are proposed for the oxidation of allenes and alkynes by the PCWP-H2O2 system.

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  • A NEW SYNTHETIC METHOD OF PREPARING IODOHYDRIN AND BROMOHYDRIN DERIVATIVES THROUGH IN-SITU GENERATION OF HYPOHALOUS ACIDS FROM H5IO6 AND NABRO3 IN THE PRESENCE OF NAHSO3

    H MASUDA, K TAKASE, M NISHIO, A HASEGAWA, Y NISHIYAMA, Y ISHII

    JOURNAL OF ORGANIC CHEMISTRY   59 ( 19 )   5550 - 5555   1994.9

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    Hypohydrous acids such as hypoiodous acid (IOH) and hypobromous acid (BrOH) were found to be easily generated from H5IO6 and NaBrO3 in the presence of an appropriate reducing agent such as NaHSO3. Iodohydrin and bromohydrin derivatives were synthesized in good yields from the reaction of a wide variety of organic compounds bearing carbon-carbon double bonds, with H5IO6 or NaBrO3 and NaHSO3. The iodohydroxylation of internal alkenes was achieved with high stereoselectivity to give anti products, although no stereoselectivity was observed in the bromohydroxylation of these alkenes. It was found that allylic alcohols undergo iodohydroxylation in anti-Markovnikov fashion to form iodo diols in good yields. Treatment of alkynes with H5IO6 combined with NaHSO3 afforded the corresponding ketones in fair yields, but the same treatment with NaBrO3 rather than H5IO6 produced the corresponding alpha,alpha-dibromo ketones along with small amounts of the dibromoalkenes.

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  • OXIDATION OF PHENOLS AND HYDROQUINONES BY DIOXYGEN CATALYZED BY MIXED ADDENDA HETEROPOLYOXOMETALATE ON ACTIVE-CARBON (NPV6MO6/C)

    S FUJIBAYASHI, K NAKAYAMA, Y NISHIYAMA, Y ISHII

    CHEMISTRY LETTERS   7号1345頁 ( 7 )   1345 - 1348   1994.7

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    Vanadomolybdophosphate supported on active carbon, NPV6Mo6/C, catalyzed the oxidation and coupling reaction of 2,3,6-trimethylphenol by dioxygen to give trimethyl-p-benzoquinone and 4,4'-dihydroxy-2,2',3,3',5,5'-hexamethylbiphenyl, respectively, depending on the solvent used. Hydroquinones and benzyl alcohol were selectively dehydrogenated by the present system, giving the corresponding p-benzoquinones and benzaldehyde, respectively, in good yields.

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  • BAEYER-VILLIGER OXIDATION OF KETONES USING MOLECULAR-OXYGEN AND BENZALDEHYDE IN THE ABSENCE OF METAL-CATALYSTS

    K KANEDA, S UENO, T IMANAKA, E SHIMOTSUMA, Y NISHIYAMA, Y ISHII

    JOURNAL OF ORGANIC CHEMISTRY   59 ( 11 )   2915 - 2917   1994.6

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    A combination system of molecular oxygen, benzaldehyde, and carbon tetrachloride oxidizes various ketones to give lactones and esters in high yields at 40 degrees C, and addition of benzoyl chloride increases yields of the Baeyer-Villiger oxidation products at a lower temperature of 20 degrees C.

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  • SELECTIVITY IN OXIDATION OF SULFIDES WITH HYDROGEN-PEROXIDE BY [PI-C5H5N+(CH2)15CH3]3PM12O40(3-) AND [PI-C5H5N+(CH2)15CH3]3(PO4[M(O)(O2)2]4)3- (M=MO OR W)

    Y ISHII, H TANAKA, Y NISHIYAMA

    CHEMISTRY LETTERS   1号1頁 ( 1 )   1 - 4   1994.1

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    Dramatical difference in selectivity was observed in the hydrogen peroxide oxidation of sulfides by [pi-C5H5N+(CH2)15CH3]3PW12O403- (CWP) and [pi-C5H5N+(CH2)15CH3]3{PO4[W(O)(O2)2]4}3- (PCWP) under the two-phase system using chloroform as the solvent. The oxidation of sulfides with 35% H2O2 by CWP afforded the corresponding sulfoxides in high selectivity (93-99%), while the same oxidation by PCWP gave sulfones exclusively.

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  • OXIDATION OF ORGANIC SUBSTRATES BY MOLECULAR-OXYGEN ALDEHYDE HETEROPOLYOXOMETALATE SYSTEM

    M HAMAMOTO, K NAKAYAMA, Y NISHIYAMA, Y ISHII

    JOURNAL OF ORGANIC CHEMISTRY   58 ( 23 )   6421 - 6425   1993.11

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    Heteropolyoxometalate-catalyzed oxidations of organic compounds such as olefins and cyclic ketones with molecular oxygen in the presence of an aldehyde were examined. Olefins were epoxidized with dioxygen in the presence of 2 equiv of 2-methylpropanal under the influence of a catalytic amount of the mixed heteropolyoxometalate NPV6Mo6 (3) to give the corresponding epoxides in moderate to good yields. This catalytic oxidation method was also applied to the epoxidation of allylic and homoallylic alcohols. In the absence of olefins, the aldehydes were efficiently converted into the corresponding carboxylic acids. In addition, the Baeyer-Villiger oxidation of cyclic ketones was accomplished by using benzaldehyde instead of 2-methylpropanal as the aldehyde.

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  • OXIDATION OF BENZYLIC DERIVATIVES WITH DIOXYGEN CATALYZED BY MIXED ADDENDA METALLOPHOSPHATE CONTAINING VANADIUM AND MOLYBDENUM

    K NAKAYAMA, M HAMAMOTO, Y NISHIYAMA, Y ISHII

    CHEMISTRY LETTERS   1699頁 ( 10 )   1699 - 1702   1993.10

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    Mixed addenda heteropolyoxometalate, NPV6Mo6, was found to be an efficient catalyst for the oxidative dehydrogenation of a variety of benzylic amines to the corresponding Schiff-base imines with molecular oxygen in toluene solution. Under the same reaction conditions, isochroman and indan were respectively oxidized to 3,4-dihydroisocoumarin and 1-indanone with high selectivity.

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  • Selective Dimerization of Aldehydes to Esters Catalyzed by Zirconocene and Hafnocene Complexes Reviewed

    NISHIYAMA Yutaka

    Organometallic   12巻9号3748頁   1993.9

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  • SELECTIVE DIMERIZATION OF ALDEHYDES TO ESTERS CATALYZED BY ZIRCONOCENE AND HAFNOCENE COMPLEXES

    K MORITA, Y NISHIYAMA, Y ISHII

    ORGANOMETALLICS   12 ( 9 )   3748 - 3752   1993.9

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    Zirconocene and hafnocene complexes such as Cp2MH2 and Cp2M(Cl)H (M = Zr or Hf) were found to catalyze efficiently the selective dimerization of aldehydes to esters under mild conditions. Hafnocene complexes exhibited higher activity than the corresponding zirconocene complexes, while titanocene complexes were inert in the present reaction. The reaction was found to be markedly influenced by the structure of the aldehydes used. Cross-dimerization could be achieved by allowing Cp2ZrH2 or Cp2Zr(Cl)H to react with two different aldehydes whose reactivities are slightly different from each other.

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  • Direct Synthesis of Polysubstituted Cyclopentanones from Ketones and Aldehydes Catalyzed by Zirconium Compounds Reviewed

    NISHIYAMA Yutaka

    The Journal of Organic Chemistry   58巻16号4497頁   1993.7

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  • DIRECT SYNTHESIS OF POLYSUBSTITUTED CYCLOPENTENONES FROM KETONES AND ALDEHYDES CATALYZED BY ZIRCONIUM COMPOUNDS

    T YUKI, M HASHIMOTO, Y NISHIYAMA, Y ISHII

    JOURNAL OF ORGANIC CHEMISTRY   58 ( 16 )   4497 - 4499   1993.7

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  • INTERMOLECULAR RADICAL-ADDITION OF 1-ALKOXYALKYL RADICALS TO VINYL DERIVATIVES

    Y NISHIYAMA, H YAMAMOTO, S NAKATA, Y ISHII

    CHEMISTRY LETTERS   5号841頁 ( 5 )   841 - 844   1993.5

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    1-Alkoxyalkyl radicals [R1R2(OR3)C.], which were generated from 1-alkoxy-1-(phenylseleno)alkanes [R1R2C(OR3)SePh] and n-Bu3SnH in the precence of AIBN, participate effectively in intermolecular addition to vinyl compounds bearing electron-withdrawing or radical stabilizing substituents to give the corresponding ethers in moderate to good yields.

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  • 酸素/アルデヒド/ヘテロポリ酸系を用いた酸化反応

    西山 豊

    The Journal of Organic Chemistry   58巻23号6421頁   1993

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  • バナジウムとモリブデンの混合型ヘテロポリ酸を触媒とす るベンジル誘導体の酸素酸化

    西山 豊

    Chemistry Letters   10号1699頁   1993

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  • Intermolecular Radical Addition of ┣T00210┫-Alkoxyalkyl Radicals to Vinyl Derivatives Reviewed

    NISHIYAMA Yutaka

    Chemistry Letters   4号841頁   1993

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  • Oxidation of Aromatic Amines with Hydrogen Peroxide Catalyzed by CetylpyridiniumHeteropolyoxometalates Reviewed

    NISHIYAMA Yutaka

    The Journal of Organic Chemistry   58巻14号3633頁   1993

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  • Oxidation of Aromatic Amines with Hydrogen Peroxide Catalyzed by Cetylpyridinium Heteropolyoxometalates

    Sigeki Sakaue, Takashi Tsubakino, Yutaka Nishiyama, Yasutaka Ishii

    Journal of Organic Chemistry   58 ( 14 )   3633 - 3638   1993

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    Various substituted anilines 1 were selectively converted into the corresponding nitrosobenzenes 2 or nitrobenzenes 3 by oxidation with aqueous hydrogen peroxide catalyzed by heteropolyoxometalates. The oxidations of anilines 1 with 35% H2O2 catalyzed by peroxotungstophosphate (PCWP) at room temperature in chloroform under two-phase conditions afforded nitrosobenzenes 2 with high selectivity. When the same reactions were carried out at higher temperature (e.g., refluxing chloroform), nitrobenzenes 3 were obtained in good yields. The oxidation of aniline (1a) with dilute H2O2 catalyzed by PCWP (2 wt %) in an aqueous medium produced azoxybenzene (4a) with high selectivity. Phenylazoxyalkanes 7 were prepared by the first direct cooxidation of 1a in the presence of primary aliphatic amines 6. For example, the oxidation of a 1:2 mixture of 1a and hexylamine (6b) with 35% H2O2 (6 equiv) in the presence of PCWP produced phenylazoxyhexane (7b) (51%) along with a small amount of 4a (8%). The reaction path for the conversion of anilines to azoxy-, nitroso-, and nitrobenzenes is described. © 1993, American Chemical Society. All rights reserved.

    DOI: 10.1021/jo00066a012

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  • GENERATION AND REACTION OF SAMARIUM(II) IODIDE EQUIVALENT FROM SAMARIUM AND CHLOROTRIMETHYLSILANE SODIUM-IODIDE SYSTEM IN ACETONITRILE

    N AKANE, Y KANAGAWA, Y NISHIYAMA, Y ISHII

    CHEMISTRY LETTERS   12号2431頁 ( 12 )   2431 - 2434   1992.12

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    Samarium(II) iodide equivalent was generated from metallic samarium and Me3SiCl/Nal reagent in acetonitrile under ambient conditions. Dehalogenation of alpha-halocarbonyl compounds and reductive coupling of ketones were successfully carried out by the use of the samarium(II) species, thus generated, in acetonitrile.

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  • ALPHA-SELECTIVE COUPLING REACTIONS OF ALLYLIC ALCOHOLS WITH ALDEHYDES USING ME3SICL/NAI/H2O-SN

    Y KANAGAWA, Y NISHIYAMA, Y ISHII

    JOURNAL OF ORGANIC CHEMISTRY   57 ( 25 )   6988 - 6991   1992.12

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  • A CONVENIENT SYNTHESIS OF EPOXIDES FROM OLEFINS USING MOLECULAR-OXYGEN IN THE ABSENCE OF METAL-CATALYSTS

    K KANEDA, S HARUNA, T IMANAKA, M HAMAMOTO, Y NISHIYAMA, Y ISHII

    TETRAHEDRON LETTERS   33 ( 45 )   6827 - 6830   1992.11

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    The system consisting of molecular oxygen and aldehydes (e.g., isobutyraldehyde and pivalaldehyde) oxidizes various olefins to give epoxides in high yield's at 40-degrees-C for 3 - 6 h.

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  • Selenium-Assisted Reduction of ┣T00210┫- and ┣T00220┫-Diketones with Carbon Monoxide and Water Reviewed

    NISHIYAMA Yutaka

    Tetrahedron Letters   33巻42号6347頁   1992.10

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  • SELENIUM-ASSISTED REDUCTION OF ALPHA-DIKETONE AND BETA-DIKETONE WITH CARBON-MONOXIDE AND WATER

    Y NISHIYAMA, J INOUE, K TERANISHI, M MORIWAKI, S HAMANAKA

    TETRAHEDRON LETTERS   33 ( 42 )   6347 - 6350   1992.10

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    Phenyl substituted alpha- (PhC(=O)C(=O)R) and beta-diketones (PhC(=O)CHRC(=O)R') are reduced by carbon monoxide and water in the presence of elemental selenium to give the corresponding aromatic ketones in moderate to good yields.

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  • OXIDATION OF ALIPHATIC-AMINES AND AROMATIC-AMINES WITH HYDROGEN-PEROXIDE CATALYZED BY PEROXOHETEROPOLY OXOMETALATES

    S SAKAUE, Y SAKATA, Y NISHIYAMA, Y ISHII

    CHEMISTRY LETTERS   2号289頁 ( 2 )   289 - 292   1992.2

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    Peroxotungstophosphate (PCWP) was found to be an efficient catalyst for the oxidation of amines with 35% H2O2 under the biphasic or homogeneous condition. Thus, primary and secondary amines were oxidized to oximes and nitrones, respectively, in good yields. Aromatic amines afforded to the corresponding nitroso compounds and/or nitrobenzenes.

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  • 酸素を用いたオレフィンからエポキシドの合成

    西山 豊

    Tetrahedron Letters   23巻45号6827頁   1992

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    科研費基盤研究

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  • クロロトリメチルシラン/ヨウ化ナトリウム/サマリウムか らのヨウ化サマリウム等価体の発生法

    西山 豊

    Chemistry Letters   12号2431頁   1992

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  • SYNTHETIC APPLICATION OF SELENOSTANNANES - SELENOALKOXYLATION OF ACETALS

    Y NISHIYAMA, S AOYAMA, S HAMANAKA

    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS   67 ( 1-4 )   267 - 270   1992

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  • ┣T00210┫-Selective Coupling Reactions of Allylic Alcohols with Aldehydes Using Me3SiCl/NaI/H2O-Sn Reviewed

    NISHIYAMA Yutaka

    The Journal of Organic Chemistry   57巻25号6988頁   1992

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  • SYNTHESIS OF MONOSELENOACETALS USING DIISOBUTYLALUMINUM BENZENESELENOLATE

    Y NISHIYAMA, S NAKATA, S HAMANAKA

    CHEMISTRY LETTERS   10号1775頁 ( 10 )   1775 - 1776   1991.10

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    Monoselenoacetals can be synthesized from the reaction of acetals with diisobutylaluminium benzeneselenolate (i-Bu2AlSePh) under mild conditions in good yields. Diselenoacetals are also obtained by treating acetals with large excess amount of i-Bu2AlSePh.

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  • SYNTHESIS UTILIZING REDUCING ABILITY OF CARBON-MONOXIDE - A NEW METHOD FOR SELECTIVE SYNTHESIS OF DIORGANYL SELENIDES AND DISELENIDES USING A SELENIUM CARBON-MONOXIDE WATER REACTION SYSTEM

    Y NISHIYAMA, A KATSUURA, A NEGORO, S HAMANAKA, N MIYOSHI, Y YAMANA, A OGAWA, N SONODA

    JOURNAL OF ORGANIC CHEMISTRY   56 ( 12 )   3776 - 3780   1991.6

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    A new approach to the synthesis of diorganyl selenides and diselenides is described. Selective generation of tertiary amine salts of hydrogen selenide ([HSe-].[R3NH+]) and hydrogen diselenide ([HSe2-].[R3NH+]) has been achieved by controlling the reaction conditions for the reduction of elemental selenium with carbon monoxide and water in the presence of tertiary amine. Subsequent alkylation provided a wide variety of symmetrical dialkyl selenides (R2Se) and diselenides (R2Se2) with a high degree of selectivity. Acylation of the amine salt of hydrogen selenide by equimolar amounts of acid chlorides led to the formation of tertiary amine salt of selenocarboxylates [R3NH+].[RCOSe-] in excellent yields. Further acylation and alkylation of this salt yielded bis(acyl) selenides [(RCO)2Se] and Se-alkyl selenocarboxylates (RCOSeR'), respectively. Moreover, oxidation of the amine salt of selenocarboxylates gave rise to bis(acyl) diselenides [(RCO)2Se2].

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  • New Agents for the Selective Reduction of the Carbon-Carbon Double Bond of┣T00210┫,┣T00220┫-Unsaturated Carbonyl Compounds Reviewed

    NISHIYAMA Yutaka

    The Journal of Organic Chemistry   56巻23号6720頁   1991

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  • Selenium‐Catalyzed debromination of vic‐dibromoalkanes and α‐bromo ketones with carbon monoxide and water

    Yutaka Nishiyama, Susumu Katsuen, Hiroshi Jounen, Sawako Hamanaka, Akiya Ogawa, Noboru Sonoda

    Heteroatom Chemistry   1 ( 6 )   467 - 474   1990

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    Selenium has been found to be an excellent catalyst for the reductive debromination of some organic bromides with carbon monoxide and water: vic‐dibromoalkanes and α‐halo ketones can be reduced to the corresponding alkenes and ketones respectively in moderate to high yields. Copyright © 1990 VCH Publishers, Inc.

    DOI: 10.1002/hc.520010607

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  • Reactions of Diphenyl Alkanes with Carbon Monoxide in the Presence of AlCl3-HCl Reviewed

    NISHIYAMA Yutaka

    Chemistry Express   5巻5号293頁   1990

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  • BIS(ACYL) DISELENIDES AS CONVENIENT ACYLATING REAGENTS

    Y NISHIYAMA, A KATSUURA, Y OKAMOTO, S HAMANAKA

    CHEMISTRY LETTERS   10号1825頁 ( 10 )   1825 - 1826   1989.10

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  • SELECTIVE REDUCTION OF ALPHA,BETA-UNSATURATED CARBONYL-COMPOUNDS WITH CARBON-MONOXIDE AND WATER ASSISTED BY SELENIUM

    Y NISHIYAMA, Y MAKINO, S HAMANAKA, A OGAWA, N SONODA

    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN   62 ( 5 )   1682 - 1684   1989.5

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  • Utilization of the Debromination by Selenium-Carbon Monoxide-Water System

    NISHIYAMA Yutaka

    9巻3号35頁   1989

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  • CARBONYL TO METHYLENE CONVERSION - SELENIUM-ASSISTED REDUCTION OF AROMATIC KETONES WITH CARBON-MONOXIDE AND WATER

    Y NISHIYAMA, S HAMANAKA, A OGAWA, N KAMBE, N SONODA

    JOURNAL OF ORGANIC CHEMISTRY   53 ( 6 )   1326 - 1329   1988.3

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  • SELENIUM, CARBON-MONOXIDE, AND WATER AS A NEW REDUCTION SYSTEM - REDUCTIVE CLEAVAGE OF DISULFIDES AND DISELENIDES TO THIOLS AND SELENOLS

    A OGAWA, Y NISHIYAMA, N KAMBE, S MURAI, N SONODA

    TETRAHEDRON LETTERS   28 ( 28 )   3271 - 3274   1987

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  • Reductive Thiolation of Aromatic Ketones and Aldehydes with Sulfur. Corbon Monoxide and WaterLeading to Thiols Reviewed

    NISHIYAMA Yutaka

    NIPPON KAGAKU KAISHI   7号1502頁 ( 7 )   1502 - 1504   1987

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    Language:Japanese   Publisher:The Chemical Society of Japan  

    The reductive thiolation of aromatic ketones and aldehyde has been investigated. Hydrogen sulfide, generated in situ from elemental sulfur, carbon monoxide, and water, reacted with various aromatic ketones and aldehyde to give the corresponding thiols in moderate to good yields.

    DOI: 10.1246/nikkashi.1987.1502

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  • REDUCTIVE SELENATION OF ALIPHATIC-KETONES AND ALDEHYDES BY SELENIUM, CARBON-MONOXIDE, AND WATER LEADING TO SYMMETRICAL DISELENIDES

    Y NISHIYAMA, S HAMANAKA, A OGAWA, S MURAI, N SONODA

    SYNTHETIC COMMUNICATIONS   16 ( 9 )   1059 - 1066   1986

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Books

  • 化学系のための安全工学

    西山 豊, 柳 日香, 高橋 大輔, 角井 伸次

    化学同人  2017 

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  • 現代有機工業化学

    西山 豊, 神戸 宣明, 安田 誠, 赤井 周司, 角井 伸次, 冨田 育義, 中 建介

    化学同人  2010 

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  • Bromorhenium Pentacarbonyl, Electronic Encyclopedia of Reagents for Organic Synthesis

    NISHIYAMA Yutaka( Role: Sole author)

    John Wiley&Sons  2007 

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  • サルファーケミカルズのフロンティア

    西山 豊( Role: Sole author)

    第6章 一酸化炭素と単体硫黄を利用する有機合成  2007 

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  • 実験化学講座 有機化合物の合成

    西山 豊( Role: Sole author)

    丸善  2004 

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  • Organoselenium Chemistry : Practical Approach in Chemistry Reviewed

    NISHIYAMA Yutaka( Role: Sole author)

    1999 

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  • Reductions with Selenium Reagents

    NISHIYAMA Yutaka( Role: Joint author)

    Organoselenium Chemistry: A Practical Approach, Oxford University Press  1999 

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  • Encyclopedia of Reagents for Organic Synthesis Reviewed

    NISHIYAMA Yutaka( Role: Joint author)

    1999 

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  • Development of New Synthetic Reactions Using Samarium Compounds As Catalysts Reviewed

    NISHIYAMA Yutaka( Role: Joint author)

    Reviews on Heteroatom Chemistry  1997 

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  • 混合配位型ヘテロポリ酸塩を触媒とする酸素酸化反応

    西山 豊( Role: Joint author)

    関西大学工業技術研究所 技苑  1995 

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  • New Generation Method for a Samarium(II) Equivalent : Me3SiX (X=Br andI)/Sm-Assisted Intermolecular Carbon-Carbon BondForming Reactions for Carbonyl Compounds Reviewed

    NISHIYAMA Yutaka( Role: Joint author)

    The Journal of Organic Chemistry  1994 

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    Grant-in-Aid for Scientific Research on Priority Areas

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  • Asymmtric Synthesis Using Metarocere Complexs

    NISHIYAMA Yutaka( Role: Sole author)

    Organometallic News  1992 

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MISC

  • The Mathematics of Minor Keys: Using positional relationships of semitones to explain the different moods of major and minor keys (Special Issue of the Faculty of Business Administration)

    Nishiyama Yutaka

    Osaka Keidai ronshu   64   125 - 132   2013.11

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    Why is it that scales beginning with an A note feel sad? Seven-note scales are composed of five whole tones and two semitones. The position of the semitones determines whether the key is major or minor. Not all music in a minor scale necessarily sounds sad, but the arrangement of notes in major and minor scales plays a large role in determining the mood of music.

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  • The Mathematics of the Straw Flute

    Nishiyama Yutaka

    Osaka Keidai ronshu   64   21 - 28   2013.9

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  • The "52 Cycling Cards" Trick Using Modular Artithmetic (Special Issue of the Faculty of Economics)

    Nishiyama Yutaka

    Osaka Keidai ronshu   64   49 - 56   2013.7

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    Ordering 52 playing cards according to a particular rule allows one to perform a certain magic trick. By learning the rule, after viewing a given card the performer will be able to predict the next card in the deck. The key to the trick is an application of modular arithmetic, one that the author hopes will lend itself as an interesting device for mathematics education.

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  • The Three-Color Triangle Problem (Essays in Memory of the Late Professor Yukio Ito)

    Nishiyama Yutaka

    Osaka Keidai ronshu   64   9 - 20   2013.5

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    Place elements in the form of an inverted triangle, and color them from top to bottom by row according to some rule. When doing so, is it possible to predict the color of the element that becomes the triangle's botttom vertex? It turns out that when you begin with a triangle of 4,10,28, ... elements in its top row, knowing the colors of that row's leftmost and rightmost elements in sufficient to predict the color of that bottom vertex, and this article presents an elegant proof of this surprising result. Coloring triangles is simple even for children, but this problem provides a springboard to learning about some advanced mathematics, including Abelian groups, the superposition principle, and fractal structures.

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  • Beautiful theorems of geometry as Van Aubel's theorem (Speical Issue of the Faculty of Human Sciences; Studies Presented to Prof. Mikio Nakao on his Retirement)

    Nishiyama Yutaka

    Osaka Keidai ronshu   63   131 - 138   2013.3

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    There is much beauty to be found among the theorems of geometry. This article introduces Van Aubel's theorem (1878), and provides proofs using (i) vectors and complex numbers and (ii) elementary geometry. The beauty of this theorem lies both in the theorem itself and also in its proofs. The appearance of geometry problems in university entrance examinations has declined dramatically since the adoption of mark sheets. Geometry is one of mathematics' great resources, and the author suggests the revival of geometry problems in the mathematics curriculum.

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  • Flexible geometry: the topology of an entangled ring puzzle (Special Issue of the Faculty of Information Technology and Social Sciences)

    Nishiyama Yutaka

    Osaka Keidai ronshu   63   19 - 26   2013.1

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    This article introduces the weird world of topology using a coin and string puzzle. The puzzle is based on the 'African ball', and its mathematical structure is explained. Human levitation and entanglement puzzles involve many uses of topology, and the author believes these kinds of wonderful mathematical ideas may be put to good use in society and government. Presenting students with familiar and appealing educational resources is also important in the teaching mathematics.

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  • Pattern matching probabilities and paradoxes--A new vaiation on Penney's coin game (Special Issue of the Faculty of Business Administration)

    Nishiyama Yutaka

    Osaka Keidai ronshu   63   269 - 276   2012.11

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    This paper gives an outline of an interesting probability game related to coin arrangements discovered by Walter Penney in 1969, and explains John Conway's concept of leading numbers and his algorithm for using them to automatically calculate mutual odds of winning. I will show that Conway's elegant algorithm is correct by using average waiting times as proposed by Stanley Collings, and discuss the effect of applying the rules of this coin game to a card game instead.

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  • The Kruskal Principle

    Nishiyama Yutaka

    Osaka Keidai ronshu   63   53 - 60   2012.9

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    Martin Kruskal invented an interesting card trick. After thoroughly shuffling and laying out a deck of cards, you use card values to determine how many cards to advance. Starting on the either the 1st or 2nd card in the series, you will end up at the same location with a very high probability. This can also be applied to Steve Humble's "walking game", which I will describe as we use geometric distributions and Markov chains to calculate probabilities and further investigate this mystery.

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    Other Link: http://www.i-repository.net/il/meta_pub/G0000031Repository_01003397

  • The probability of cards meeting after a shuffle (Special Issue of the Faculty of Economics; Studies Presented to Prof. Hiroshi Izumi, Prof. Kazuko Mano on Their Retirement)

    Nishiyama Yutaka

    Osaka Keidai ronshu   63   149 - 155   2012.7

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    Even after giving a standard 52-card deck a good shuffle, there will likely be instances where two cards with the same number end up next to each other. This article concerns my investigations into the probability of such ann occurrence. In the end I found that this is by no means an uncommmon event, there being a 21.7% probability of finding two cards of a given number adjacent, and a 95.4% chance of finding at least one pair of adjacent same-numbered cards. I made these calculations using combinations for up to 20 cards, and a random number-based simulation for the cases of 24 to 52 cards.

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  • Unit Fractions that Sum to 1

    Nishiyama Yutaka

    Osaka Keidai ronshu   63   21 - 28   2012.5

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    This paper presents and solves a problem related to decomposing 1 into a sum of unit fractions. Decomposition into two terms, composition of two terms, decomposition into three terms, and other methods are used to find ways to maximize the number of unique terms, and a decomposition into 42 terms is demonstrated.

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  • Benham's top (Special Issue of the Faculty of Human Sciences; Studies Presented to Prof. Ryuichi Kobayashi on his Retirement)

    Nishiyama Yutaka

    Osaka Keidai ronshu   62   87 - 94   2012.3

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    It is still a mystery why colors emerge from the black and white pattern of Benham's top. After a brief overview of previous research on subjective colors, this article explains the nature of color and how we humans perceive a color. This article also introduces a hypothesis about subjective colors based on neuronal simulation, the characteristics of sensation, and in particular neural transmission delay.

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  • Why \200\ notes are unpopular (Special Issue of the Faculty of Information Management)

    Nishiyama Yutaka

    Osaka Keidai ronshu   62   1 - 6   2012.1

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    The Japanese government issued new \2000 yen notes as part of the year 2000 millennial celebrations, but contrary to expectations they are rarely seen in circulation. While there are existing mathematical theories about the best denominations to use to minimize the amount of change given in financial transactions, this problem can also be reexamined as a difference between Eastern and Western cultures and their respective predilection for even and odd numbers, which might explain why the \2000 bill has not taken root here.

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  • The Mathematics of Direction in Writing (Special Issue of the Faculty of Business Administration)

    Nishiyama Yutaka

    Osaka Keidai ronshu   62   109 - 116   2011.11

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    This artilce explains historically the reason why the order in which characters are written in English is from left to right, but in Arabic it is from right to left. There were all patterns of direction in writing: horizontal or vertical, right to left, left to right, reversed character horizontally or vertically, 90 degreee rotation. Ancient Hieroglyphs had all patterns, but English, Arabic and Kanji differed. Another expects those may deeply relate to ritht hand manner.

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  • Fixed Points in Similarity Transformations (Essays in Memory of the Late Professor Hiroyasu Yamada)

    Nishiyama Yutaka

    Osaka Keidai ronshu   62   129 - 136   2011.9

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    A new method of constructing fixed points in congruence transformations is introduced, and a detailed explanation of fixed points in similarity transformations then follows. Constructions in Euclidean geometry generally require the use of a compass and ruler, but the new method is very simple, requiring the use of only a ruler. The new construction can also be applied to affine transformations.

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  • Burnside's Lemma (Special Issue of the Faculty of Economics; Studies Presented to Prof. Tsuneto Yamamoto, Associate Prof. Takumi Sasano on Their Retirement)

    Nishiyama Yutaka

    Osaka Keidai ronshu   62   205 - 212   2011.7

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    There is a famous problem which involves discriminating the faces of a die using 3 colors: how many different patterns can be produced? This article introduces Burnside's lemma which is a powerful method for handling such problems. It requires a knowledge of group theory, but is not so difficult and is likely to be understood by elementary school pupils.

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  • Machin's Formula and Pi

    Nishiyama Yutaka

    Osaka Keidai ronshu   62   1 - 8   2011.5

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    This article explains the calculation of Pi historically, focusing on Machin's formula. Archimedes' formula is shown first, followed by Machin's formula using Gregory's formula. Machin's formula makes particularly ingenious use of the tan double and quadruple angle trigonometric addition formulae. The chapter closes with an explanation of Takano's formula.

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  • The Brachistochrone Curve: The Problem of Quickewst Descent (Special Issue of the Faculty of Human Sciences; Studies Presented to Prof. Mieko Sakurai, Prof. Kunio Tanaka, Prof. Teruo Tarumoto on Their Retirement)

    Nishiyama Yutaka

    Osaka Keidai ronshu   61   309 - 316   2011.3

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    This article presents tyhe problem of quickest descent, or the Brachistochrone curve, that may be solved by the calculus of variations and the Euler-Lagrange equation. The cycloid is the quickest curve and also has the property of isochronism by which Huygens improved on Galileio's pendulum.

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  • Gauss' Method of Constructing a Regular Heptadecagon (Special Issue of the Faculty of Information Management)

    Nishiyama Yutaka

    Osaka Keidai ronshu   61   11 - 20   2011.1

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    This article explains how to construct a regular heptadecagon according to the theory of cyclotonic equations which was discovered by Gauss in 1796. The author also shows how to construct any root or fraction.

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  • Sudoku: the New Smash Hit Puzzle Game (Special Issue of the Faculty of Business Administration)

    Nishiyama Yutaka

    Osaka Keidai ronshu   61   205 - 212   2010.11

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    Sudoku is now popular in many countries. This article explains the history and mathematics behind sudoku. This includes the basic rules of sudoku, a trial-and-error solution method, a discussion of the number of patterns completed, minimum sudoku, and the application of Euler's Latin squares. The popularity of sudoku in the UK is also discussed.

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  • Calculating √2

    Nishiyama Yutaka

    Osaka Keidai ronshu   61   43 - 50   2010.9

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  • Unexpected Probabilities (Special Issue of the Faculty of Economics; Studies Presented to Prof. Saburo Honda on his Retirement)

    Nishiyama Yutaka

    Osaka Keidai ronshu   61   345 - 352   2010.7

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    This article presents 2 unexpected probabilities. If there are at least 23 people in a class, then the probability that there is a shared birthday exceeds one half. This is explained by the idea of complementary events. What are the chances of there being a student who ends up in the same seat when everyone in the class is reseated? This probability is arount 2/3 irrespective of the number of students, and was solved by Montmort(1708).

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  • Synthesis of Alkynes by the Reaction of 1, 1-Dihaloalkenes with Lanthanum Metal

    ANAHARA Namika, YUASA Takumi, UMEDA Rui, NISHIYAMA Yutaka

    ( 56 )   26 - 27   2010.5

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  • Numerical plaindromes and the 196 Problem (Essays in Memory of the Late Satoshi Okuda, Lecturer at Osaka University of Economics)

    Nishiyama Yutaka

    Osaka Keidai ronshu   61   157 - 163   2010.5

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    The numbers 727,1991,38483 and so on, are the same when read forwards or backwards. These numbers are known as numerical plaindromes. Let's pick an arbitrary number, recorded the digits in reverse and add it to the original number. It is said that repeating this operation eventurally leads to a plaindrome. Numbers in the sequence derived from 196 however, do not yield a plaindrome. This is an unresolved mathematical problem.

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  • Turning Things Inside Out (Special Issue of the Faculty of Human Sciences)

    Nishiyama Yutaka

    Osaka Keidai ronshu   60   197 - 204   2010.3

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    This article presents 3 puzzles which turn things inside out: the cube puzzle, turning a paper strip inside out, and hexaflexagons. Readers who wish to find the solutions for themselves are advised not to read the full explanations.

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  • Counting with the Fingers (Special Issue of the Faculty of Information Management; Studies Presented to Prof. Izumi Watanabe on his Retirement)

    Nishiyama Yutaka

    Osaka Keidai ronshu   60   17 - 24   2010.1

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    It has been written that across the world there are 17 types of counting method using the fingers. For example, there are various methods for starting to count 'one' by bending their left little finger. Counting using the fingers differs according to region, ethnicity, and historical period. This chapter also discusses the 'evolutionary theory' of counting methods.

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  • Cultures of Curves and Staright Lines (Special Issue of the Faculty of Business Administration)

    Nishiyama Yutaka

    Osaka Keidai ronshu   60   131 - 138   2009.11

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    Japanese buildings are constructed with straight lines. European buildings however, tend to have arched rather than straight horizontal lines. Roofs, window frames and the tops of doors are often arched. Euroeapn buildings are made not from wood but from stone. The reason for these differences is explained by mechanical theory.

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  • From Oldham's Coupling to Air Conditioners

    Nishiyama Yutaka

    Osaka Keidai ronshu   60   77 - 84   2009.9

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    Oldham's coupling is a really interesting device. It is possible to understand the method with a knowledge of only junior high-school geometry. Compressors in air conditioners also use this idea, where involute curves are used for the teeth of the cogs in the compressor. Mathematics doesn't just reside in textbooks; it's alive in our daily lives.

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  • Sicherman Dice: Equivalent Sums with a Pair of Dice (Special Issue of the Faculty of Economics; Studies Presented to Prof. Akira Shigemori on his Retirement)

    Nishiyama Yutaka

    Osaka Keidai ronshu   60   185 - 192   2009.7

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    George Sicherman discovered an interesting pair of dice whose sums have the same probalitiy distribution as a pair of standard dice, and this was reported by Martin Gardner in 1978. This pair of dice is numbered, 1,3,4,5,6,8 and 1,2,2,3,3,4, and is unique. In order to prove the uniqueness of his combination three methods are shown: trial-and-error with pencil and paper, a Visual Basic program, and factorization of polynomials. The third is the most elegant solution and was presented by Gallian and Rusin, as well as Broline in 1979.

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  • Miura Folding: Applying Origami to Space Exploration

    Nishiyama Yutaka

    Osaka Keidai ronshu   60   17 - 24   2009.5

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    Miura folding is famous all over the world. It is an element of the ancient Japanese tradition of origami and reaches as far as astronautical engineering throught the construction of solar panels. This article explains how to achieve the Miura folding, and describes its application to maps. The author also suggests in this context that nature may abhor the right angle, according to observation of the wing base of a dragonfly.

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  • What's in a Barcode?: Duplicated Combinations (Special Issue of the Faculty of Human Sciences; Studies Presented to Prof. Motoo Mitsuda on his Retirement)

    Nishiyama Yutaka

    Osaka Keidai ronshu   59   147 - 155   2009.3

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    This article explains how barcodes are read mathematically. One numeral is constructed from 7 modules in a barcode. Firstly, a counting method is presented through which the number of different characters which can be expressed is obtained. After touching upon formulae for permutations and combinations, duplicated combinations are expressed explicitly. The use of a modulus of 10 is mentioned with regard to the calculation of check digits.

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  • Increasing and Decreasing of Areas (Special Issue of the Faculty of Information Management; Studies Presented to Prof. Yoshiharu Matsumoto on his Retirement)

    Nishiyama Yutaka

    Osaka Keidai ronshu   59   15 - 21   2009.1

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    This article explains how to help junior-high school students enjoy studying geometry using some card magic. Area may be increased and decreased by arranging pieces of card according to the images on either the front or back of the card. There are some interesting stories associated with this puzzzle, including 'Sunflowers Facing the Sun' and 'The UFO-Spotting Brothers.'

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  • Measuring Areas: from Polygons to Land Maps (Special Issue of the Faculty of Business Administration)

    Nishiyama Yutaka

    Osaka Keidai ronshu   59   149 - 155   2008.11

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    This article explains how to measure are using both simple and complicated measurement methods. Elementary school children obtain area by counting triangles; junior-high school students use Cartesian coordinates; and high-school students study Heron's formula. In this article additional methods such as the trapezoid formula and Amsler's linear planimeter are presented.

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  • Opening the Black Box of Random Numbers

    Nishiyama Yutaka

    Osaka Keidai ronshu   59   1 - 7   2008.9

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    Random numbers are frequently used all around us, but many people do not know the basis of random numbers. After touching upon prime numbers and prime nember thoery, this article explains the principles of random number generation using primes and primitive roots, and explains how they are actually handled inside computers.

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  • The Sepak Takrow Ball Puzzle (Special Issue of the Faculty of Economics)

    Nishiyama Yutaka

    Osaka Keidai ronshu   59   141 - 149   2008.7

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    This article explains the truncated icosahedron by making a sepak takrow ball, which is used in a popular ball game in Thailand. Next, many popular topics for examination questions on spatial diagrams are presented such as: how many regular polyhedra can be made, Euler's polyhedron formula, F-E+V=2, and the number of regular pentagons and hexagons in a soccer ball.

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  • Stairway Light Swithces

    Nishiyama Yutaka

    Osaka Keidai ronshu   59   11 - 18   2008.5

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    This article explains stariway light switches which can be turned on or off from different plances. This idea is based on the binary system of Boolean algebra. Mathematics is hidden everywhere in daily life and we may enjoy it if we study the mathematics relating to everyday things.

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  • The Weirdness of Number 6174 (Special Issue of the Faculty of Human Sciences; Studies Presented to Prof. Shigeru Morikawa on his Retirement)

    Nishiyama Yutaka

    Osaka Keidai ronshu   58   93 - 100   2008.3

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    The number 6174 is a really mysterious number. At first glance, it might not seem so obvious, but as we are about to see, anyone who can subtract can uncover the mystery that makes 6174 so special.

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  • The Mathematics of Pleated Folding (Special Issue of the Faculty of Economics; Essays in Memory of the Late Professor Otohei Doi)

    Nishiyama Yutaka

    Osaka Keidai ronshu   58   253 - 261   2008.1

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    This article explains all about Hexaflexagons; how to make, how to operate them and mathematical theory. Hexaflexagons are known surfaces with no inside or outside as same as Mobius strip. Refereeing to the articles of Gardner M. and Madachy J.S. author found out the general solution for multiple foldings of Hexaflexagons.

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  • Mathematics of Fans (Special Issue of the Faculty of Information Management)

    Nishiyama Yutaka

    Osaka Keidai ronshu   58   13 - 20   2007.7

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    This paper explains why some fans appear to rotate backwards by stroboscopic effect. That phenomenon is often seen as fans in the movies. After estimating fan rotation by mathematical formulae many applications of stroboscopes are shown.

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  • Burnside's Lemma and its Application (Speical Issue of the Faculty of Information Management)

    Nishiyama Yutaka

    Osaka Keidai ronshu   57   47 - 60   2007.1

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  • Culture and History of Numbers

    NISHIYAMA Yutaka

    Study of economic history : keizaishi kenkyu   8   146 - 174   2004.3

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    Other Link: http://www.osaka-ue.ac.jp/research/nikkeisi/lab/contents/08.html

  • Organic Reactions in Supercritcal Conditions

    Nishiyama Yutaka

    Engineering & technology   12 ( 4 )   51 - 52   2002.11

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  • The Flightdynamics of Boomerangs

    Nishiyama Yutaka

    Osaka Keidai ronshu   46 ( 3 )   45 - 132   1995.9

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  • Puzzle "Once Upon a Time in Japan"

    Nishiyama Yutaka

    Osaka Keidai ronshu   185   77 - 90   1988.9

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  • On a Difference Solution for Bessel Differential Equation

    Nishiyama Yutaka

    Osaka Keidai ronshu   167   111 - 115   1985.9

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▼display all

Presentations

  • Deoxygenative Dimerization of Diaryl Ketones with Lanthanum Metal under Carbon Dioxide

    Yutaka Nishiyama, R. Umeda

    Rare Earths 2016  2016.6 

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    Event date: 2016.6

    Venue:Hokkaido University, Hokkaido, Japan  

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  • Selective Synthesis of 1-Halonaphthalenes by Copper-catalyzed Benzannulation

    R. Ueda, T.Tanaka, R. Umeda, Y. Nishiyama

    2015.11 

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  • Reaction of Benzanthrone with Metal Acetylide

    Y. Shimizu, T. Namba, R. Umeda, Y. Nishiyama

    2015.11 

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  • Synthesis and Properties of 2,3-Dinaphthoquinone Derivatives Having Bulky Substituents at 1,4 Positions

    S. Nishimura, A. Ozeki, R. Umeda, Y. Nishiyama

    2015.11 

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  • Synthesis of Isocoumarins by the Rhenium-catalyzed 6-Endo Cyclization of o-Ethynylbenzoic Acids

    K. Yamashita, S. Yoshikawa, R. Umeda, Y. Nishiyama

    2015.11 

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  • Rhenium-catalyzed Reaction of Alcohol and Vinyl Acetate

    T. Yamamoto, Y. Takahashi, R. Umeda, Y. Nishiyama

    2015.11 

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  • Rhenium-Catalyzed Regioselective Synthesis of Multiple Substituted Polycyclic Aromatic Compounds

    R. Umeda, Y. Nishiyama

    2014.7 

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  • レニウム触媒を用いた新規合成反応の開発

    西山 豊

    第6回触媒化学融合研究センター講演会  2014.1 

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    Event date: 2014.1

    Venue:産総研第5事業所第2本館第4会議室  

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  • Synthesis and Photophysical Properties of 9,10-Di(3-aryl-2-naphthyl)anthracenes

    R. Umeda, M. Kimura, Y. Nishiyama, Y. Tobe

    2013.11 

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    Event date: 2013.11 - 2013.12

    Venue:Todaiji Temple Cultural Center  

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  • 無水ベンゼンセレニン酸を用いたN,N-ジアリールアミンの酸化反応

    芳村 暁, 梅田 塁, 西山 豊

    日本化学会第93春季年会  2013.3 

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    Event date: 2013.3

    Venue:立命館大学びわこ・くさつキャンパス  

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  • 一酸化炭素-セレン触媒系を用いた、ニトロブタノン誘導体からの多置換ピロール誘導体の合成

    増野 司, 梅田 塁, 西山 豊

    日本化学会第93春季年会  2013.3 

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    Event date: 2013.3

    Venue:立命館大学びわこ・くさつキャンパス  

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  • レニウム触媒存在下、アルコールとアルケニルシランの反応によるアルケン合成

    内山 浩平, 荒木 奈々瀬, 梅田 塁, 西山 豊

    日本化学会第93春季年会  2013.3 

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    Event date: 2013.3

    Venue:立命館大学びわこ・くさつキャンパス  

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  • ベンゾフェノンと求電子試薬との反応

    問屋俊介, 梅田 塁, 西山 豊

    日本化学会第93春季年会  2013.3 

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    Event date: 2013.3

    Venue:立命館大学びわこ・くさつキャンパス  

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  • 一酸化炭素を利用した含ヘテロ化合物合成

    西山 豊, 梅田 塁

    第17回関西大学先端科学技術シンポジウム  2013.1 

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    Event date: 2013.1

    Venue:関西大学100周年記念会館  

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  • 一酸化炭素-セレン触媒系を利用した多置換ピロールの効率的合成

    増野 司, 梅田 塁, 西山 豊

    第17回関西大学先端科学技術シンポジウム  2013.1 

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    Venue:関西大学100周年記念会館  

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  • 電極活物質への利用を目的とした拡張パイ共役分子の合成と物性

    梅田 塁, 西山 豊

    第17回関西大学先端科学技術シンポジウム  2013.1 

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    Event date: 2013.1

    Venue:関西大学100周年記念会館  

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  • p-メチレンキノン構造を組み込んだ縮環型芳香族ケトンの合成と物性

    中務雅教, 梅田 塁, 西山 豊

    合同研究発表会(日本エネルギー学会関西支部 第57回研究発表会、石油学会関西支部 第21回研究発表会)  2012.12 

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    Event date: 2012.12

    Venue:大阪大学中之島センター  

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  • フェニルアセトアルデヒド等価体とアルキンの反応による1,2-二置換ナフタレンの選択的合成

    西 悟, 梅田 塁, 西山 豊

    合同研究発表会(日本エネルギー学会関西支部 第57回研究発表会、石油学会関西支部 第21回研究発表会)  2012.12 

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    Event date: 2012.12

    Venue:大阪大学中之島センター  

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  • セレン触媒存在下、ニトロブタノン誘導体と一酸化炭素の反応によるピロール誘導体の合成

    増野 司, 梅田 塁, 西山 豊

    第39回 有機典型元素化学討論会  2012.12 

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    Event date: 2012.12

    Venue:いわて県民情報交流センター(アイーナ)  

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  • ベンゾフェノンと金属ランタンより発生させた活性種の反応

    問屋俊介, 梅田 塁, 西山 豊

    第32回有機合成若手セミナー  2012.11 

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    Event date: 2012.11

    Venue:神戸薬科大学ききょう記念ホール  

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  • ベンズアントロンへの位置選択的アリール、アミノ基の導入法の開発

    梅田 塁, 難波輝壮, 中務雅教, 西山 豊

    第32回有機合成若手セミナー  2012.11 

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    Venue:神戸薬科大学ききょう記念ホール  

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  • p-メチレンキノン構造を有する拡張π共役分子の合成と物性

    中務雅教, 早川真人, 梅田 塁, 西山 豊

    第23回基礎有機化学討論会  2012.9 

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    Event date: 2012.9

    Venue:京都テルサ  

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  • ベンズアヌレーション反応を利用した立体的に込み合った9,10-ジナフチルアントラセン誘導体の合成と物性

    木村正宏, 梅田 塁, 西山 豊, 戸部義人

    第23回基礎有機化学討論会  2012.9 

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    Venue:京都テルサ  

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  • レニウム触媒を用いたフェニルアセトアルデヒドジメチルアセタールとアルキンとの反応による、1,2-二置換ナフタレンの位置選択的合成

    西 悟, 梅田 塁, 西山 豊

    第59回有機金属化学討論会  2012.9 

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    Venue:大阪大学吹田キャンパス  

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  • Facile Synthesis of 2,2'-Binaphthyl Derivatives by Benzannulation Reaction

    H. Tabata, R. Umeda, Y. Nishiyama, Y. Tobe

    2012.9 

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  • Synthesis and Physical Properties of π-Extended Molecules Having p-Methylenequione Unit

    M. Nakatsukasa, M. Hayakawa, R. Umeda, Y. Nishiyama

    2012.9 

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  • Regioselective Synthesis of 1,2-Disubstituted Naphthalenes: Rhenium-Catalyzed Coupling Reaction of Alkynes with Phenylacetaldehyde Dimethylacetal

    S. Nishi, R. Umeda, Y. Nishiyama

    2012.9 

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  • Synthesis and Physical Properties of Sterically Hindered 9,10-Dinaphtylanthracenes

    R. Umeda, M. Kimura, Y. Nishiyama, Y. Tobe

    2012.9 

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  • ベンズアヌレーション反応による2,2'-ビナフチル誘導体の効率的合成

    田畑博雅, 梅田 塁, 西山 豊, 戸部義人

    第39回有機反応懇談会  2012.8 

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    Event date: 2012.8

    Venue:関西大学千里山キャンパス  

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  • 無水ベンゼンセレニン酸を用いたアニリン類の酸化反応

    芳村 暁, 梅田 塁, 西山 豊

    第39回有機反応懇談会  2012.8 

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    Venue:関西大学千里山キャンパス  

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  • p-メチレンキノン骨格を導入したπ共役拡張インデノンの合成と物性

    早川真人, 中務雅教, 梅田 塁, 西山 豊

    第39回有機反応懇談会  2012.8 

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    Venue:関西大学千里山キャンパス  

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  • Oxidation of N,N-Diarylamines with Benzenseleninic Anhydride

    A. Yoshimura, R. Umeda, Y. Nishiyama

    2012.5 

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  • レニウム触媒を用いたベンズアヌレーション反応による2,2'-ビナフチル誘導体の合成

    田畑博雅(B), 梅田 塁, 西山 豊

    日本化学会第92春季年会  2012.3 

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    Event date: 2012.3

    Venue:慶応義塾大学日吉・矢上キャンパス  

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  • ベンゼンならびにナフタレン環が高密度に集積化したらせん分子の合成と構造

    梅田 塁, 森下 滋(D), 西山 豊, 戸部義人(大阪大学)

    日本化学会第92春季年会  2012.3 

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    Venue:慶応義塾大学日吉・矢上キャンパス  

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  • 6,12-ジアリールインデノ[1,2-b]フルオレン誘導体の合成と物性

    中務雅教(D), 梅田 塁, 西山 豊

    日本化学会第92春季年会  2012.3 

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    Venue:慶応義塾大学日吉・矢上キャンパス  

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  • レニウム触媒存在下、フェニルアセトアルデヒドジメチルアセタールと芳香族アルキンの反応による1,2-二置換ナフタレンの選択的合成

    西 悟 (D), 梅田 塁, 西山 豊

    日本化学会第92春季年会  2012.3 

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    Venue:慶応義塾大学日吉・矢上キャンパス  

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  • 二酸化炭素雰囲気下、カルボニル化合物と金属ランタンの反応

    問屋俊介(D), 梅田 塁, 西山 豊

    日本化学会第92春季年会  2012.3 

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    Event date: 2012.3

    Venue:慶応義塾大学日吉・矢上キャンパス  

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  • 遷移金属触媒を利用した縮合多環芳香族化合物ならびにパイ電子が高密度に集積したらせん分子の合成

    梅田 塁, 西山 豊

    第16回関西大学先端科学技術シンポジウム  2012.1 

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    Event date: 2012.1

    Venue:関西大学100周年記念会館  

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  • 金属未使用プロセスの開発:セレンならびに硫黄触媒系を利用した含窒素ヘテロ環化合物の新規合成法の創出

    小牧祐也 (D), 梅田 塁, 西山 豊

    第16回関西大学先端科学技術シンポジウム  2012.1 

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    Venue:関西大学100周年記念会館  

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  • La触媒を用いた二酸化炭素常圧下でのエポキシドからの環状カーボネート合成

    森下 滋(D), 梅田 塁, 西山 豊

    第16回関西大学先端科学技術シンポジウム  2012.1 

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    Venue:関西大学100周年記念会館  

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  • 環状カーボネート類縁体の1,3-オキサチオラン-2-オンの合成と電解液の添加剤としての利用

    西山 豊, 梅田 塁

    第16回関西大学先端科学技術シンポジウム  2012.1 

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    Venue:関西大学100周年記念会館  

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  • Synthesis of Multiple 2,3-Disubstituted Naphthalenes by Rhenium-Catalyzed Benzannulation of o-Alkynylbenzaldehyde with Alkynes

    S. Morishita (D), K. Kaiba (D), R. Umeda, Y. Nishiyama, Y. Tobe (Osaka Univ.)

    2011.12 

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  • ベンズアントロンと有機金属試薬との反応

    難波輝壮 (D), 梅田 塁, 西山 豊

    合同研究発表会(日本エネルギー学会関西支部 第56回研究発表会、石油学会関西支部 第21回研究発表会)  2011.12 

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    Event date: 2011.12

    Venue:(財)京都教育文化センター  

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  • レニウム触媒を用いたアルコールとビニルアセテート誘導体の反応によるカルボニル化合物合成

    高橋侑己(D), 梅田 塁, 西山 豊

    合同研究発表会(日本エネルギー学会関西支部 第56回研究発表会、石油学会関西支部 第20回研究発表会)  2011.12 

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    Venue:(財)京都教育文化センター  

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  • 金属ランタンを直接用いる還元反応

    西山 豊

    日本希土類学会第29回講演会  2011.11 

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    Venue:千里阪急ホテル  

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  • Benzannulation Approach to Synthesis of Highly Elaborated Helical Molecules Having 2,3-Disubstituted Naphthalene Units

    R. Umeda, S. Morishita (D), Y. Nishiyama, Y. Tobe (Osaka Univ.)

    2011.10 

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  • ベンズアヌレーション反応を利用したナフタレン骨格が高度に集積化したらせん分子の合成

    梅田 塁, 森下 滋(D), 西山 豊, 戸部義人(大阪大学)

    第22回基礎有機化学討論会  2011.9 

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    Event date: 2011.9

    Venue:つくば国際会議場  

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  • ベンズアントロンと様々な有機金属試薬との反応による一段階置換基導入法の開発

    難波輝壮 (D), 梅田 塁, 西山 豊

    第22回基礎有機化学討論会  2011.9 

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    Event date: 2011.9

    Venue:つくば国際会議場  

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  • p-メチレンキノン構造によって拡張した縮環型芳香族ケトンの合成と構造・物性

    中務雅教(D), 梅田 塁, 西山 豊

    第22回基礎有機化学討論会  2011.9 

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    Event date: 2011.9

    Venue:つくば国際会議場  

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  • レニウム触媒を用いたアルキンとo-アルキニルベンズアルデヒドとのベンズアヌレーションによる複数の2,3-二置換ナフタレン骨格を有する化合物の合成

    森下 滋(D), 飼馬健太 (D), 梅田 塁, 西山 豊, 戸部義人(大阪大学)

    第58回有機金属化学討論会  2011.9 

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    Event date: 2011.9

    Venue:名古屋大学東山キャンパス  

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  • フルオレノン、キサントン、アクリジン骨格を有する拡張共役パイ電子化合物の合成と物性

    中務雅教(D), 梅田 塁, 西山 豊

    第38回有機反応懇談会  2011.8 

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    Event date: 2011.8

    Venue:大阪府立大学なかもずキャンパス  

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  • レニウム触媒存在下、フェニルアセトアルデヒドジメチルアセタールとアルキンの反応

    西 悟 (D), 梅田 塁, 西山 豊

    第38回有機反応懇談会  2011.8 

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    Event date: 2011.8

    Venue:大阪府立大学なかもずキャンパス  

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  • レニウム触媒によるベンズアヌレーション反応を利用したパイ電子高集積化芳香族化合物の合成

    梅田 塁, 森下 滋(D), 西山 豊, 戸部義人(大阪大学)

    第38回有機反応懇談会  2011.8 

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    Event date: 2011.8

    Venue:大阪府立大学なかもずキャンパス  

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  • Benzannulation of o-Alkynylbenzaldehyde with Alkyne to Highly Elaborated Polycyclic Aromatic Compounds

    R. Umeda, S. Morishita (D), K. Kaiba (D), Y. Nishiyama, Y. Tobe (Osaka Univ.)

    2011.7 

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    Event date: 2011.7

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  • パイ電子過剰系複素環にナフタルイミドが縮環した蛍光ソルバトクロミック分子の合成と光学特性

    西田博亮 (D), 三河拓也 (B), 乙野元宏 (B), 梅田 塁, 西山 豊

    日本化学会第91春季年会  2011.3 

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    Event date: 2011.3

    Venue:神奈川大学横浜キャンパス  

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  • ランタン化合物を触媒としたエポキシドと二酸化炭素の反応

    小牧祐也 (D), 梅田 塁, 西山 豊

    日本化学会第91春季年会  2011.3 

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    Event date: 2011.3

    Venue:神奈川大学横浜キャンパス  

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  • レニウム触媒を用いた高集積化多環式芳香族化合物の合成と物性

    森下 滋 (D), 飼馬健太 (D), 梅田 塁, 西山 豊, 戸部義人(大阪大学)

    日本化学会第91春季年会  2011.3 

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    Event date: 2011.3

    Venue:神奈川大学横浜キャンパス  

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  • レニウム触媒を用いたビニルアセテートとアルコールの反応によるケトン合成

    高橋侑己 (D), 梅田 塁, 西山 豊

    日本化学会第91春季年会  2011.3 

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    Event date: 2011.3

    Venue:神奈川大学横浜キャンパス  

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  • レニウム触媒を用いたエーテルと酸ハロゲン化物からのエステル合成

    飼馬健太 (D), 西村 崇 (B), 田中利昌 (B), 梅田 塁, 西山 豊

    日本化学会第91春季年会  2011.3 

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    Event date: 2011.3

    Venue:神奈川大学横浜キャンパス  

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  • レニウム触媒を用いたフェニルアセトアルデヒド等価体とアルキンの反応による1,2-二置換ナフタレンの選択的合成

    西 悟 (B), 小島 彩 (B), 梅田 塁, 西山 豊

    日本化学会第91春季年会  2011.3 

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    Event date: 2011.3

    Venue:神奈川大学横浜キャンパス  

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  • ベンズアントロンと有機金属試薬との反応:6-アリールおよび6-エチニルベンズアントロンの選択的合成

    難波輝壮 (D), 梅田 塁, 西山 豊

    日本化学会第91春季年会  2011.3 

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    Event date: 2011.3

    Venue:神奈川大学横浜キャンパス  

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  • p-メチレンキノンによりパイ共役系を拡張させた縮環型芳香族ケトンの合成と物性

    中務雅教 (B), 梅田 塁, 西山 豊

    日本化学会第91春季年会  2011.3 

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    Event date: 2011.3

    Venue:神奈川大学横浜キャンパス  

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  • Rhenium-Catalyzed Benzannulation of o-Alkynylbenzaldehyde with Alkyne

    K. Kaiba (D), R. Umeda, Y. Nishiyama

    2010 International Chemical Congress of Pacific Basin Societies (PACIFICHEM 2010)  2010.12 

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    Event date: 2010.12

    Venue:Hawaii Convention Center, Honolulu, Hawai, USA  

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  • Synthesis and Properties of Aryl and Ethynyl Substitutied Benzanthrone Derivatives

    T. Namba (D), R. Umeda, Y. Nishiyama

    2010 International Chemical Congress of Pacific Basin Societies (PACIFICHEM 2010)  2010.12 

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    Event date: 2010.12

    Venue:Hawaii Convention Center, Honolulu, Hawai, USA  

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  • Selenium-Catalyzed Reductive Deoxygenation of Various Aromatic Nitro Compounds with Carbon Monoxide

    S. Morishita (D), R. Umeda, Y. Nishiyama

    2010 International Chemical Congress of Pacific Basin Societies (PACIFICHEM 2010)  2010.12 

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    Event date: 2010.12

    Venue:Hawaii Convention Center, Honolulu, Hawai, USA  

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  • Synthesis and Properties of Novel Polyheterocyclic Aromatic Compounds Fused Naphthimide Unit

    H. Nishida (D), R. Umeda, Y. Nishiyama

    2010 International Chemical Congress of Pacific Basin Societies (PACIFICHEM 2010)  2010.12 

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    Event date: 2010.12

    Venue:Hawaii Convention Center, Honolulu, Hawai, USA  

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  • Synthesis of 2,1-Benzisoselenazoles and their Complexation toward Copper Salts

    N. Nemoto (D), R. Umeda, Y. Nishiyama

    2010 International Chemical Congress of Pacific Basin Societies (PACIFICHEM 2010)  2010.12 

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    Event date: 2010.12

    Venue:Hawaii Convention Center, Honolulu, Hawai, USA  

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  • Synthesis of Cyclic Carbonates: Lanthanum Metal Compound Catalyzed Reaction of Epoxides with Carbon Dioxide

    Y. Komaki (D), R. Umeda, Y. Nishiyama

    2010 International Chemical Congress of Pacific Basin Societies (PACIFICHEM 2010)  2010.12 

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    Event date: 2010.12

    Venue:Hawaii Convention Center, Honolulu, Hawai, USA  

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  • Reductive Dehalogenation of gem-Dihaloalkenes with Lanthanum Metal

    N. Anahara (D), R. Umeda, Y. Nishiyama

    2010 International Chemical Congress of Pacific Basin Societies (PACIFICHEM 2010)  2010.12 

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    Event date: 2010.12

    Venue:Hawaii Convention Center, Honolulu, Hawai, USA  

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  • Lanthanum Metal-Assisted Coupling Reaction of Diaryl Ketone with Dialkyl Ketone under Carbon Dioxide

    Y. Nishiyama, R. Narishige (D), R. Umeda

    2010 International Chemical Congress of Pacific Basin Societies (PACIFICHEM 2010)  2010.12 

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    Event date: 2010.12

    Venue:Hawaii Convention Center, Honolulu, Hawai, USA  

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  • 二次電池の電極材料を指向した多段階酸化還元能を有する新規有機パイ電子系の創出

    梅田 塁, 西山 豊

    第15回関西大学先端科学技術シンポジウム  2010.12 

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    Event date: 2010.12

    Venue:関西大学100周年記念会館  

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  • 2,1-ベンズイソセレナゾールの合成とその利用

    根本紀彦 (D), 栗山将行 (B), 梅田 塁, 西山 豊

    第37回有機典型元素化学討論会  2010.11 

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    Event date: 2010.11

    Venue:室蘭市民会館ホール  

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  • 一酸化炭素-セレン触媒系を利用したインドロ[1,2-c]キナゾリノン誘導体のOne-pot合成

    森下 滋 (D), 梅田 塁, 西山 豊

    第30回有機合成若手セミナー  2010.11 

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    Event date: 2010.11

    Venue:大阪府立大学学術交流会館  

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  • ナフタルイミドが縮環した非対称なカルバゾールならびにジベンゾフランの光学特性

    西田博亮 (D), 乙野元宏 (B), 三河拓也 (B), 梅田 塁, 西山 豊

    第30回有機合成若手セミナー  2010.11 

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    Event date: 2010.11

    Venue:大阪府立大学学術交流会館  

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  • レニウム触媒を用いたo-アルキニルベンズアルデヒドとアルキンによる選択的な2,3-二置換ナフタレンの合成

    飼馬健太 (D), 梅田 塁, 西山 豊

    第30回有機合成若手セミナー  2010.11 

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    Event date: 2010.11

    Venue:大阪府立大学学術交流会館  

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  • 金属ランタンを用いる還元的脱ハロゲン化を利用した高反応性化学種の発生

    穴原菜美香 (D), 梅田 塁, 西山 豊

    第30回有機合成若手セミナー  2010.11 

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    Event date: 2010.11

    Venue:大阪府立大学学術交流会館  

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  • ベンズアントロンとアリールおよびエチニル金属試薬との反応

    難波輝壮 (D), 梅田 塁, 西山 豊

    第30回有機合成若手セミナー  2010.11 

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    Event date: 2010.11

    Venue:大阪府立大学学術交流会館  

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  • レニウム触媒を用いたアルコールとビニルアセテートからのケトンおよびアルデヒド合成

    高橋侑己 (D), 梅田 塁, 西山 豊

    第30回有機合成若手セミナー  2010.11 

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    Event date: 2010.11

    Venue:大阪府立大学学術交流会館  

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  • ランタンを触媒としたエポキシドと二酸化炭素からの環状カーボネート合成

    小牧祐也 (D), 梅田 塁, 西山 豊

    第30回有機合成若手セミナー  2010.11 

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    Event date: 2010.11

    Venue:大阪府立大学学術交流会館  

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  • 2,1-ベンズイソセレナゾールの合成とキノリン誘導体への変換

    根本紀彦 (D), 栗山将行 (B), 梅田 塁, 西山 豊

    第30回有機合成若手セミナー  2010.11 

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    Event date: 2010.11

    Venue:大阪府立大学学術交流会館  

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  • Synthesis and Photophysical Properties of Carbazoles and Dibenzofurans Having Naphthalimide Unit

    R. Umeda, H. Nishida (D), T. Mikawa (B), M. Otono (B), Y. Nishiyama

    The Sixth International Symposium on Integrated Synthesis (ISIS-6)  2010.10 

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    Event date: 2010.10

    Venue:Seaside Hotel Maiko Villa Kobe, Hyogo, Japan  

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  • レニウム触媒を用いたo-アルキニルベンズアルデヒドとアルキンのベンズアヌレーション反応を利用した2,3-二置換ナフタレン誘導体合成

    飼馬健太 (D), 梅田 塁, 西山 豊

    第57回有機金属化学討論会  2010.9 

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    Event date: 2010.9

    Venue:中央大学多摩キャンパス  

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  • ナフトイミドが縮環した非対称なカルバゾールならびにジベンゾフラン誘導体の合成と蛍光ソルバトクロミック特性

    西田博亮 (D), 乙野元宏 (B), 三河拓也 (B), 梅田 塁, 西山 豊

    第21回基礎有機化学討論会  2010.9 

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    Event date: 2010.9

    Venue:名古屋大学東山キャンパス  

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  • ナフタルイミドが縮環した非対称なカルバゾール誘導体の合成と光学特性

    梅田 塁, 西田博亮 (D), 三河拓也 (B), 乙野元宏 (B), 西山 豊

    第27回有機合成化学セミナー  2010.9 

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    Event date: 2010.9

    Venue:シーサイドホテル舞子ビラ神戸  

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  • 1,1-ジハロアルケンと金属ランタンの反応を利用したアルキン合成

    穴原菜美香 (D), 湯浅拓実 (D), 梅田 塁, 西山 豊

    第27 回希土類討論会  2010.5 

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    Event date: 2010.5

    Venue:北九州国際会議場  

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  • 2,1-ベンズイソセレナゾールとアルキンの反応を利用したキノリン誘導体の合成

    西山 豊, 村田実奈子

    第89回日本化学会春季年会  2009.3 

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    Event date: 2009.3

    Venue:千葉  

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  • 一酸化炭素-セレン触媒反応系を利用したニトロ化合物の還元反応

    西山 豊, 西田博亮

    第89回日本化学会春季年会  2009.3 

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    Event date: 2009.3

    Venue:千葉  

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  • 1,3,2-ジオキサセレノラン-2-オキシド触媒を用いたアルケンの酸化反応

    西山 豊, 神田栄司

    第89回日本化学会春季年会  2009.3 

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    Event date: 2009.3

    Venue:千葉  

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  • 2,1-ベンズイソセレナゾールの新規合成法

    西山 豊, 今井悠介

    第89回日本化学会春季年会  2009.3 

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    Event date: 2009.3

    Venue:千葉  

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  • 金属ランタンを用いた1,1-ジハロアルケンの脱ハロゲン化反応

    西山 豊, 湯浅拓実

    第89回日本化学会春季年会  2009.3 

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    Event date: 2009.3

    Venue:千葉  

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  • レニウム触媒を用いたケテンシリルアセタールとカルボニル化合物の反応

    西山 豊, 飼馬健太

    第89回日本化学会春季年会  2009.3 

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    Event date: 2009.3

    Venue:千葉  

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  • ジフェニルジセレニド触媒存在下, カルボニル化合物とジフェニルジスルフィドの反応

    西山 豊, 安房宏章

    第89回日本化学会春季年会  2009.3 

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    Event date: 2009.3

    Venue:千葉  

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  • プロジェクトで得られた電気二重層キャパシタに関する新技術

    西山 豊, 石川正司, 山縣雅紀, 荒川隆一

    第13回関西大学先端科学技術シンポジウム,プロジェクトセッション 「将来型電気エネルギー社会を支える 『キャパシタ型蓄電システム』 の開発」  2009 

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    Event date: 2009

    Venue:関西大学, 吹田市  

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  • 二酸化セレンと2-メチルフェニルイソシアネートおよび2-メチルアニリンの反応

    西山 豊, 今井悠介

    第35回有機典型元素化学討論会  2008.12 

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    Event date: 2008.12

    Venue:東京  

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  • 1,3,2-ジオキサセレノラン-2-オキシドを用いたアルキンの酸化反応

    西山 豊, 神田栄司

    第35回有機典型元素化学討論会  2008.12 

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    Event date: 2008.12

    Venue:東京  

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  • Oxidation of Alkynes with Cyclic Selenite, The Fifth International Symposium on Integrated Synthesis

    NISHIYAMA Yutaka, E. Kanda

    The Fifth International Symposium on Integrated Synthesis  2008.9 

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    Event date: 2008.9

    Venue:Kobe  

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  • 二酸化セレンとo-アミノトルエンの反応を用いたイソセレナゾールの新規合成法

    西山 豊, 今井悠介

    第35回有機反応懇談会  2008.8 

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    Event date: 2008.8

    Venue:大阪市立大学  

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  • 環状セレナイトを用いたアルキン類の触媒的酸化法

    西山 豊, 神田栄司

    第35回有機反応懇談会  2008.8 

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    Event date: 2008.8

    Venue:大阪市立大学  

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  • 金属ランタン存在下,gem-ジハロアルカンとアリルアルコールの反応

    西山 豊, 湯浅拓実, 谷水はな

    第25回希土類討論会  2008.5 

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    Event date: 2008.5

    Venue:東京  

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  • 一酸化炭素-セレン触媒系を利用した脂肪族ニトロ化合物の還元反応

    西山 豊, 池田定達

    日本化学会第88回春季年会  2008 

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    Event date: 2008

    Venue:立教大学  

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  • 無水ベンゼンセレニン酸を用いた芳香族イソシアネートのベンゾキノンイミン誘導体への変換反応

    西山 豊, 今井悠介

    日本化学会第88回春季年会  2008 

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    Event date: 2008

    Venue:立教大学  

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  • 環状セレナイトを用いたアルキンの酸化反応

    西山 豊, 神田栄司

    日本化学会第88回春季年会  2008 

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    Event date: 2008

    Venue:立教大学  

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  • 金属ランタン存在下,gem-ジハロアルカンとアリルアルコール誘導体の反応

    西山 豊, 湯浅拓実

    日本化学会第88回春季年会  2008 

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    Event date: 2008

    Venue:立教大学  

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  • セシウム塩触媒存在下,ジフェニルジカルコゲニドを用いたカルボニル化合物のα-フェニルカルコゲニド化反応

    西山 豊, 小熊友也

    日本化学会第88回春季年会  2008 

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    Event date: 2008

    Venue:立教大学  

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  • レニウム触媒を用いたアリルシランとイミンの[4+2]付加環化反応

    西山 豊, 木内克則

    日本化学会第88回春季年会  2008 

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    Event date: 2008

    Venue:立教大学  

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  • 金属ランタンを用いる,ジアリールケトンの二酸化炭素雰囲気下でのカップリング反応

    西山 豊, 桐山雅成

    日本化学会第88回春季年会  2008 

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    Event date: 2008

    Venue:立教大学  

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  • ジスルフィドを用いたアルキンのモノチオ化反応

    西山 豊, 河端泰輝, 上西祐平

    日本化学会第88回春季年会  2008 

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    Event date: 2008

    Venue:立教大学  

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  • 有機合成反応へのランタノイド金属の利用-特徴ある反応をめざして-

    西山 豊

    第34回有機反応懇談会  2007.7 

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    Event date: 2007.7

    Venue:大阪府立大学  

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  • 芳香族イソシアネート無水ベンゼンセレニン酸の反応

    西山 豊, 今井悠介

    第34回有機典型元素化学討論会  2007 

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    Event date: 2007

    Venue:大阪大学  

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  • 金属ランタンを用いるgem-ジハロアルカンからのカルベンの発生

    西山 豊, 湯浅拓実

    日本化学会第87回春季年会  2007 

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    Event date: 2007

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  • 無水ベンゼンセレニン酸を用いたイソシアネ-トからのナイトレノイドの発生法

    西山 豊, 今井悠介

    日本化学会第87回春季年会  2007 

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    Event date: 2007

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  • レニウム触媒を用いたイミンとアリルシランの反応

    西山 豊, 板井基和

    日本化学会第87回春季年会  2007 

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  • 二酸化炭素雰囲気下, 金属ランタンを用いたジアリールケトンとアルキルアリールケトンのカップリング反応

    西山 豊, 秋吉利泰

    日本化学会第87回春季年会  2007 

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    Event date: 2007

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  • セシウム塩存在下, ジフェニルジカルコゲニドとアルキンの反応

    西山 豊, 小熊友也

    日本化学会第87回春季年会  2007 

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  • 環状セレライトを用いたアルコールの酸化反応

    西山 豊, 神田栄司

    日本化学会第87回春季年会  2007 

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  • セレン触媒を用いたジスルフィドと一酸化炭素, アミンの反応

    西山 豊, 河端泰輝, 小熊友也

    日本化学会第87回春季年会  2007 

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  • 環状セレナイトを用いたアルコール類の酸化反応

    西山 豊, 神田栄司

    第34回有機典型元素化学討論会  2007 

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    Event date: 2007

    Venue:大阪大学  

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  • セシウム塩触媒存在下,アルキンとジフェニルジカルコゲニドとの反応

    西山 豊, 小熊友也, 大西晴子

    第34回有機典型元素化学討論会  2007 

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    Event date: 2007

    Venue:大阪大学  

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  • Cesium Salt Catalyzed Bisphenylchalcogenation of Alkynes with Diphenyl Dichalcogenides

    NISHIYAMA Yutaka, Y. Koguma, H. Ohnishi

    54th Symposium on Organometallic Chemistry  2007 

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    Event date: 2007

    Venue:Japan, Hiroshima Univ  

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  • Lanthanum Metal-Assisted Reaction of Diaryl Ketones with Alkyl Aryl Ketones under Carbon Dioxide

    NISHIYAMA,Yutaka, T. Akiyoshi, R. Narishige

    14th IUPAC International Symposium on Organometallic Chemistry Directed Towards Organic Synthesis  2007 

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    Event date: 2007

    Venue:Nara  

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  • セシウム塩存在下, ジフェニルジカルコゲニドを用いたアセチレン類のビスフェニルカルコゲニド化反応

    西山 豊, 小熊友也, 大西晴子

    第33回有機典型元素化学討論会  2006.12 

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    Event date: 2006.12

    Venue:福岡  

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  • A New Method for the Synthesis of 1,3-Oxathiolan- 2-ones by the Reaction of Oxiranes with Carbon Monoxide and Sulfur

    NISHIYAMA Yutaka, C. Katahira

    22nd International Symposium on the Organic Chemistry of Sulfur  2006.8 

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    Event date: 2006.8

    Venue:Saitama  

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  • Formation of Dithiocarbonates by the Reaction of Disulfide with Carbon Monoxide

    NISHIYAMA Yutaka

    Second Core-to-Core Symposium on Main Group Element Chemistry  2006.8 

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    Event date: 2006.8

    Venue:Tokyo  

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  • Lanthanum Metal-Assisted Reaction of Diaryl Ketones with Dialkyl Ketones under Carbon Dioxide

    NISHIYAMA Yutaka, R. Narishige

    XXII International Conference on Organometallic Chemistry  2006.7 

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    Event date: 2006.7

    Venue:Zaragoza  

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  • オレフィンの触媒的不斉酸化反応

    西山 豊

    第33回有機金属化学セミナー  2006.6 

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    Event date: 2006.6

    Venue:京都  

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  • 二酸化炭素の反応制御作用:金属ランタンを用いたジアリールケトンの新規カップリング反応

    西山 豊, 二宮雅史, 成重良麻

    第23回希土類討論会  2006.5 

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    Event date: 2006.5

    Venue:東京  

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  • 二酸化炭素の反応制御作用に基づく, 金属ランタン存在下, ジアリールケトンの新規カップリング反応

    西山 豊, 成重良麻

    日本化学会第86春季年会  2006 

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    Event date: 2006

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  • 有機合成反応への希土類金属の利用-特徴ある反応をめざして-

    西山 豊

    第13回希土類サマースクール  2005 

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    Event date: 2005

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  • Lanthanum Metal-Assisted Cyclopropanation of Alkenes with gem-Dihaloalkanes

    NISHIYAMA Yutaka, H. Tanimizu, N. Sonoda

    Pacifichem 2005  2005 

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    Event date: 2005

    Venue:Honolulu  

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  • Lanthanum Metal-Assisted Cyclopro panation of Alkenes with gem-Dihaloalkanes

    NISHIYAMA Yutaka, H. Tanimizu, N. Sonoda

    The Third International Symposium on Integrated Synthesis 2005 (ISIS-3)  2005 

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    Event date: 2005

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  • Lanthanum Metal-Assisted Reaction of Diaryl Ketones with Dialkyl Ketones under an Atmosphere of Carbon Dioxide

    NISHIYAMA Yutaka, R. Narishige, N. Sonoda

    The Third International Symposium on Integrated Synthesis 2005 (ISIS-3)  2005 

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  • 触媒を用いる酸化反応

    西山 豊

    第32回有機金属化学セミナー  2005 

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  • 金属ランタン存在下, gem-ジハロアルカンとアルケンの反応

    西山 豊, 谷水はな, 園田 昇

    第22回希土類討論会  2005 

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  • テトラキス(ジメチルアミノ)エチレン(TDAE)を用いるα―ハロケトンの脱ハロゲン化反応

    西山 豊, 小林昭裕, 園田 昇

    日本化学会第85春季年会  2005 

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  • エチレン・一酸化炭素のラジカル共重合に基づく二塩基酸の合成

    西山 豊, 高橋貞充, 園田 昇

    日本化学会第85春季年会  2005 

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  • イソシアナートと無水ベンゼンセレニンの反応より発生させたナイトレノイドの利用

    西山 豊, 中嶋亜希, 園田 昇

    日本化学会第85春季年会  2005 

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  • 銅塩存在下,ジフェニ―ルジセレニドとアルキンの反応

    西山 豊, 岩本雅子

    日本化学会第85春季年会  2005 

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  • 環状セレナイトエステルの合成と酸化剤としての利用

    西山 豊, 富田真裕

    日本化学会第85春季年会  2005 

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  • 二酸化炭素雰囲気下,金属ランタンを用いたジアリールケトンとジアルキルケトンのカップリング反応

    西山 豊, 成重良麻, 二宮雅史, 園田 昇

    日本化学会第85春季年会  2005 

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  • 金属ランタン存在下,gem―ジハロアルカンとアルケンの反応

    西山 豊, 谷水はな, 園田 昇

    日本化学会第85春季年会  2005 

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  • A Novel Reaction of Diaryl Ketones with Lanthanum Metal under an Atmosphere of Carbon Dioxide

    NISHIYAMA Yutaka, R. Narishige, N. Sonoda

    52nd Symposium on Organometallic Chemistry  2005 

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    Event date: 2005

    Venue:Japan  

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  • Lanthanum Metal-Assisted Reaction of Diaryl Ketones under Carbon Dioxide

    NISHIYAMA Yutaka, R. Narishige, N. Sonoda

    Pacifichem 2005  2005 

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    Event date: 2005

    Venue:Honolulu  

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  • 環状セレナイトの合成とその利用

    西山 豊, 富田真裕, 宮藤 聖

    第32回ヘテロ原子化学討論会  2005 

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  • Facile Method for the Synthesis of 1, 3-Oxathiolan-2-ones by Reaction of Oxiranes Sulfur and Carbon Monoxide

    NISHIYAMA Yutaka, C. Katahira, N. Sonoda

    Pacifichem 2005  2005 

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    Event date: 2005

    Venue:Honolulu  

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  • A New Method for the Synthesis of 1, 3-Oxathiolan-2-ones by the Reaction of Epoxides with Carbon Monoxide and Sulfur

    NISHIYAMA Yutaka, T. Katahira, N. Sonoda

    International Symposium on Integrated Synthesis 2004 (ISIS2004)  2004 

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    Event date: 2004

    Venue:Awaji  

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  • Selenium-Catalyzed Synthesis of Carbonothioates

    NISHIYAMA Yutaka, K. Inazawa, N. Sonoda

    International Symposium on Integrated Synthesis 2004 (ISIS2004)  2004 

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    Event date: 2004

    Venue:Awaji  

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  • Lanthanum Metal Assisted Reaction of DiarylKetones with Dialkyl Ketones under Carbon Monoxide

    NISHIYAMA Yutaka, R. Narishige, N. Sonoda

    51st Symposium on Organometallic Chemistry  2004 

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    Event date: 2004

    Venue:Japan  

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  • セレン触媒を用いたジスルフィドと一酸化炭素の反応

    西山 豊, 稲澤幸治, 園田 昇

    第31回ヘテロ原子化学討論会  2004 

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  • エポキシドと一酸化炭素,硫黄の反応による1,3―オキサチオラン―2―オンの新規合成法

    西山 豊, 片平知里, 園田 昇

    第31回ヘテロ原子化学討論会  2004 

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  • テトラキス(ジメチルアミノ)エチレン(TDAE)を用いた1,2―ビス(ハロゲノメチル)ベンゼンの脱ハロゲン化反応

    西山 豊, 小林昭裕, 園田 昇

    日本エネルギー学会関西支部第49回研究発表会  2004 

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  • エチレンと一酸化炭素のラジカル共重合に基づく二塩基酸合成

    西山 豊, 高橋貞充, 園田 昇

    第34回石油・石油化学討論会  2004 

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  • エポキシと一酸化炭素,硫黄の反応による1,3―オキソチオラン―2―オンの新規合成法

    西山 豊, 片平知里, 園田 昇

    第34回複素環化学討論会  2004 

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  • 触媒を用いる酸化反応

    西山 豊

    第31回有機金属化学セミナー  2004 

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  • 二酸化炭素雰囲気下,ジアリールケトンと金属ランタンの反応

    西山 豊, 二宮雅史, 成重良麻, 園田 昇

    第21回希土類討論会  2004 

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  • エポキシと一酸化炭素,硫黄の反応

    西山 豊, 片平知里, 園田 昇

    石油学会第53回研究発表会  2004 

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  • Lanthanum Metal Assisted Reaction of DiarylKetones under Carbon Monoxide

    NISHIYAMA Yutaka, M. Ninomiya, N. Sonoda

    Rare Earths '04  2004 

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    Event date: 2004

    Venue:Nara, Japan  

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  • Oxidation by Using Heteropolyoxometalates

    NISHIYAMA Yutaka

    1993 

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    Event date: 1993

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  • Direct Use of Lanthanum Metal in Organic Synthesis

    Yutaka Nishiyama

    International Symposium on Organometallic Chemistry of Rare Earths 

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Research Projects

  • Development of rhenium-catalyzed carbon-carbon and carbon-heteroatom bonds

    Grant number:18K05131  2018.4 - 2022.3

    Japan Society for the Promotion of Science  Grants-in-Aid for Scientific Research  Grant-in-Aid for Scientific Research (C)

    Nishiyama Yutaka

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    Grant amount:\4290000 ( Direct Cost: \3300000 、 Indirect Cost:\990000 )

    We have recently disclosed that rhenium complex, such as ReX(CO)5 (X = Br and Cl), serves as an air and moisture-tolerant catalyst for various organic reactions instead of various Lewis acid catalysts. In the continuation of the development of rhenium-catalyzed synthetic reactions, we investigated the new carbon-carbon and carbon-heteroatom bond formations used alcohols, esters, and ethers as the carbon sources in this research. In this research, we have found the rhenium complex acts as a useful catalyst on the carbon-carbon bond formations between alcohols and organosilicon compounds such as alkenyl and allyl silanes. We also found that rhenium catalyzed the deoxygenation and silylation of alcohols by hydrosilane.
    In addition, we have shown that various polycyclic aromatic compounds, which were used as organic functional materials, were easily and efficiently synthesized by the use of rhenium complex catalyst.

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  • Rhenium-Catalyzed Selective Synthesis of Polycyclicaromatic Compounds based on the Activation of Unsaturated Bond

    Grant number:23550130  2011 - 2013

    Japan Society for the Promotion of Science  Grants-in-Aid for Scientific Research  Grant-in-Aid for Scientific Research (C)

    NISHIYAMA Yutaka, UMEDA Rui

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    Grant amount:\5200000 ( Direct Cost: \4000000 、 Indirect Cost:\1200000 )

    The polysubstituted aromatic compounds constituted an attractive class compounds from the view of chemical, biological active molecules and materials science. In this research, we have investigated the development of selective synthetic method of various multisubstituted aromatic compounds based on the activation of unsaturated bonds by rhenium catalyst.
    We now find three novel reactions, (i) the synthesis of quinolines by the reaction of aldimines, which were prepared by treatment of anilines and aldehydes, and allylic silanes, (ii) the selective synthesis of 1,2-disubstituted naphthalenes by the reaction of alkynes and o-alkynyl substituted benzaldehyde, and (iii) the selective synthesis of 2,3-disubstituted naphthalenes by the reaction of alkynes and phenylacetoaldehyde equivalents such styrene oxide or phenylacetoaldehyde dimethylacetal. As the application of these reactions, the synthesis of various orthophenylene derivatives bearing benzene and naphthalene was examined.

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  • The Development of New Reduction System by the Using Carbon Dioxide

    Grant number:18550100  2006 - 2008

    Japan Society for the Promotion of Science  Grants-in-Aid for Scientific Research  Grant-in-Aid for Scientific Research (C)

    NISHIYAMA Yutaka

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    Grant amount:\4230000 ( Direct Cost: \3600000 、 Indirect Cost:\630000 )

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  • Development of New Carbonylation Method by Carbon Monoxide and the Synthesis of Thiocarbonates

    Grant number:15550096  2003 - 2005

    Japan Society for the Promotion of Science  Grants-in-Aid for Scientific Research  Grant-in-Aid for Scientific Research (C)

    NISHIYAMA Yutaka

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    Grant amount:\3700000 ( Direct Cost: \3700000 )

    It was confirmed a unique catalytic ability of selenium on the reaction of dialkyl disulfides with carbon monoxide. The carbonylation of dialkyl disulfide with carbon monoxide was promoted by the selenium catalyst in the presence of DBU to give the corresponding dialkyl dithiocarbonates.
    When dibutyl disulfide was allowed to react with carbon monoxide in the presence of selenium catalyst and DBU as a base at 80℃ for 6h, dibutyl dithiocarbonate, which was the carbonylated product of disulfide, was obtained in 92% yield. The yield of the dithiocarbonate was influenced by the tertiary amine used as a base. The carbonylation of dialkyl disulfides such as dipropyl, dihexyl, and didecyl disulfide also proceeded smoothly in the presence of selenium catalyst to give the corresponding dialkyl dithiocarbonates in good yields. For the reaction of disulfide bearing secondary alkyl chain, the yield of the product based on reacted disulfide was high ; however, the conversion of disulfide was lower that that of primary one. In the case of tertiary dialkyl disulfide, the formation of dialkyl dithiocarbonate was not confirmed and disulfide was recovered. On the contrast, in the case of diphenyl disulfide, the carbonylated product was not obtained at all and thiol was formed in moderate yield.

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  • Development of a new Synthetic Method of Thiol Esters by Using Carbon Monoxide-Disulfide System

    Grant number:12650840  2000 - 2001

    Japan Society for the Promotion of Science  Grants-in-Aid for Scientific Research  Grant-in-Aid for Scientific Research (C)

    SONODA Noboru, NISHIYAMA Yutaka

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    Grant amount:\3600000 ( Direct Cost: \3600000 )

    The development of a convenient and efficient method for the synthesis of S-alkyl and S-arylcarbonothiolates has attracted considerable attention in synthetic and industrial chemistry. Hitherto, although many synthetic methods of S-alkyl- and S-arylcarbonothiolates have been shown, these methods consisted on a multi-step procedures: (i) the preparation of SCO by the reaction of sulfur with carbon monoxide, (ii) the nucleophilic addition of alcohol or thiol and (iii) subsequent alkylation.
    Now we found a one-pot synthetic method of S-alkyl- and S-arylcarbonothiolates by the reaition of alcohol with disulfide and carbon monoxide in the presence of a catalytic amount of selenium. For example, when ethanol was treated with diphenyl disulfide in the presence of a catalytic amount of selenium under an atmosphere pressurized of carbon monoxide, S-phenyl-O-ethylcarboncpthiolate was formed in almost quantitative yield. Similarly, diaryl disulfide substituted various functional groups were reacted with ethanol under the pressure of carbon monoxide to give the corresponding S-aryl-O-ethylcarbonothiolates in moderate to good yields. In this reaction, aliphatic alcohols can also be used as an alcohol, the corresponding thiol esters were formed in moderate yields. On the other hand, in the case of dialkyl disulfide, the mixture of S- alkyl- O- alkylcarbonothiolates and S, S- dialkylcarbonothiolates were obtained.

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  • スタニルラジカル触媒を用いたインターエレメント化合物からのビニルラジカル生成

    Grant number:11120256  1999

    日本学術振興会  科学研究費助成事業  特定領域研究(A)

    西山 豊

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    Grant amount:\2000000 ( Direct Cost: \2000000 )

    スズラジカルのセレンに対する強い親和性に着目し、本研究では1,2,3-セレナジアゾールにスズラジカルを作用させれば、1,2,3-セレナジアゾールからビニルラジカルが温和な条件下、効率良く発生できるのではないかと考え検討した。その結果、1,2,3-セレナジアゾールの分解二量化反応が触媒量のスズラジカルを共存させることで著しく促進され、1,4-ジセレニン誘導体が効率良く得られることが明らかとなった。この反応は、スズラジカルが1,2,3-セレナジアゾールのセレン上を攻撃し、セレン-スズ結合の開裂、窒素分子の脱離を経て、まずビニルラジカルが生成し、生成したビニルラジカルがもう一分子の1,2,3-セレナジアゾールと反応し、1,4-ジセレニン誘導体を生成したと考えられることで反応は上手く説明できる。このように系中でのビニルラジカル種の生成が示唆されることから、本方法により発生させたビニルラジカルの有機合成化学への利用を次に検討した。その結果、触媒量のスズラジカル共存下、1,2,3-セレナジアゾールとオレフィンの反応を行ったところ、ジヒドロセレノフェンが収率良く得られ、本反応がジヒドロセレノフェンの効率良い合成法としても利用できることを見い出した。
    本研究を通して、触媒量のスズラジカルを共存させることで1,2,3-セレナジアゾールとオレフィンの反応がジヒドロセレノフェンの簡便な合成法として利用できることを明らかにしたのみならず、従来ほとんど報告例のないスズラジカルが触媒的に働くという極めて興味深い反応を見い出すことが出来た。

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  • Development of Generation Method of Unstable Chemical Species Using Characteristics of Heteroatom Compounds

    Grant number:10450347  1998 - 1999

    Japan Society for the Promotion of Science  Grants-in-Aid for Scientific Research  Grant-in-Aid for Scientific Research (B)

    SONODA Noboru, NISHIYAMA Yutaka

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    Grant amount:\14000000 ( Direct Cost: \14000000 )

    We have investigated the new generation method of unstable chemical species by the use of the characteristics of heteroatom compounds and the utilization of these species in organic synthesis. In the course of our study, we found that nitre or nitrenoid species were generated efficiently by the reduction of aromatic nitro compounds with carbon monoxide in the presence of a catalytic amount of selenium. N-Heterocyclic compounds such as indols and 4(3H)-quinazolinones were synthesized by the selenium-catalyzed reaction of 0-nitrostyrenes and 0-nitrobenzoylamides with carbon monoxide in moderate to good yields. In addition, we have also developed the new generation method of vinyl radical via the thermal decomposition of 1,2,3-selenadiazoles. When 1,2,3-selenadiazoles were treated with olefins under thermal condition, the addition of vinyl radical generated in situ to carbon-carbon double bond and followed by intramoleculer cyclization proceeded efficiently to give the corresponding dihydroselenophenes in moderated to good yields. This reaction was hardly promoted by the addition of a catalytic amount of organostannyl radical.

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  • Development of Generation Method of Unstable Chemical Species Using Carbon Monoxide

    Grant number:10555317  1998 - 1999

    Japan Society for the Promotion of Science  Grants-in-Aid for Scientific Research  Grant-in-Aid for Scientific Research (B)

    SONODA Noboru, NISHIYAMA Yutaka

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    Grant amount:\13500000 ( Direct Cost: \13500000 )

    We investigated the new generation method of unstable chemical species by the use of the characteristics of carbon monoxide and the utilization of these unstable species in organic synthesis. In the course of this study, we found that nitre or nitrenoid species were generated smoothly by the reduction of aromatic nitro compounds with carbon monoxide in the presence of a catalytic amount of selenium. When 0-nitrostyrenes were treated with carbon monoxide in the presence of a catalytic amount of selenium, deoxyganation of nitro group followed by intramolecular cyclization proceeded efficiently to give the corresponding indols in moderate to good yields. On the reaction of 0-nitrobenzoylamides with carbon monoxide, 4(3H)-quinazolinones were synthesized in moderate to good yields. In addition, we have also developed the rhenium complexes having ligand of carbon monoxide acts as a catalyst on the Friedel-Craft alkylation of arenes with alkyl halides, Aldol type reaction of enol silyl ethers with carbonyl compounds and allylation of carbonyl compounds with allyic stannanes.

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  • セレンを含むインターエレメント化合物の特性を利用した不安定化学種生成に関する研究

    Grant number:10133253  1998

    日本学術振興会  科学研究費助成事業  特定領域研究(A)

    西山 豊

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    Grant amount:\2000000 ( Direct Cost: \2000000 )

    不安定化学種は、有機合成化学における有用な合成手法を与える反応種として多くの研究がなされている。しかし不安定化学種の発生法が極めて限定され、さらにその高い反応性のため反応の制御が困難である場合も多く、効率良く有機合成に利用した例は比較的限られている。本研究では、インターエレメント化合物の化学的特性を追及し、セレンを含むインターエレメント化合物の特性を活用した、不安定化学種の効率的発生法の開発ならびに、発生させた不安定化学種をkey speciesとする新規合成反応の開拓を目的とし検討した。その結果、エナールアセタールとジイソブチルアルミニウムフェニルセレノラートの反応により簡便かつ効率良く合成可能となった1-アルコキシ-3-フェニルセレノ-1-アルケンの脱プロトン化、続くアルキルハライド、カルボニル化合物を用いたアルキル化反応を行ったところ、完全なレジオ選択性でアルキル化反応が進行することを見い出した。また1-アルコキシ-3-フェニルセレノ-1-アルケンは、塩酸等のプロトン酸で扱うことで、β-フェニルセレノアルデヒドへ、過酸化水素水で酸化することでα,β-不飽和アルデヒドへ変換が可能である。また1,2,3-セレナジアゾールをα,β-不飽和カルボニル化合物共存下熱分解反応を行ったところ、1,2,3-セレナジアゾールのセレンα,β-不飽和カルボニル化合物に付加することで生成したと考えられるジヒドロセレノフェンが収率良く得られたことも合わせて見い出した。この結果は、1,2,3-セレナジアゾールの熱分解反応が不安定化学種であるビニルラジカルの新規発生法として利用可能であることを示している。

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  • 環状エーテル類の立体選択的合成法の開発

    Grant number:09750958  1997 - 1998

    日本学術振興会  科学研究費助成事業  奨励研究(A)

    西山 豊

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    Grant amount:\2100000 ( Direct Cost: \2100000 )

    ポリエーテル化合物の中に極めて高い生理・薬理活性を示す化合物や、イオノフォアとしての機能を示す化合物が見い出されている。それらの点からもポリエーテル化合物は天然合成化学のターゲット分子としてのみならず機能性分子としての利用にも興味が持たれて、ポリエーテル化合物の合成法の確立は大きな研究課題の一つである。しかしそれらポリエーテル化合物の合成においては、環状エーテル部位をいかに立体化学を制御しながら、効率良く構築するが力大きな問題となる。そこで本研究ではそれら環状エーテル化合物の立体選択的合成法の確立を目的とし、まずテトラヒドロフラン環に着目し検討した。その結果ルイス酸存在下、シリルシアニド、エノールシリルエーテル、アリルシラン、アリルスタナン、ジエチル亜鉛、アルコール、チオール等の求核剤と環状ヘミケタールの反応を検討したところ、種々の官能基を有する2,2,5-三置換テトラヒドロフラン誘導体が高収率かつ高立体選択的に得られることを見い出した。この手法ではテトラヒドロフラン環の2位へ種々官能基の高立体選択的導入が可能となり、多置換テトラヒドロフランの高立体選択的合成の一手法として利用できるものと考えられる。また、本反応の適用範囲の拡張を目的とし、ルイス酸存在下、二連結環状へミケタールとヒドロシランならびに求核剤を反応させたところ、多置換テトラヒドロフランダイマーが高立体選択的に得られ、本方法がテトラヒド口フランダイマーの合成法としても利用可能であることも明らかとした。

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  • ラジカル創成触媒の開発と合成反応への応用

    Grant number:09238255  1997

    日本学術振興会  科学研究費助成事業  重点領域研究

    石井 康敬, 坂口 聡, 西山 豊

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    Grant amount:\1600000 ( Direct Cost: \1600000 )

    フリーラジカルは最も反応性に富んだ化学種の一種であり、フリーラジカルを触媒的に発生させられることができれば多くの新しい反応が開発できる。我々はN-ヒドロキシフタルイミド(NHPI)が分子状酸素と反応しフリーラジカルであるフタルイミド-N-オキシルラジカル(PINO)を発生できることを見いだしている。本研究はこの点に注目し触媒量のNHPIと少量の酸素からPINOを発生させアルカンから水素を引き抜きアルキルラジカルを生成させ、これを出発物とする反応を開拓した。すなわち、アダマンタンのような環状炭化水素をNHPI(10mol%)を触媒に用い、一酸化炭素(15気圧)と空気(1気圧)よりなる混合ガスと酢酸-ジクロロメタン混合溶媒中で95℃・4時間オートクレーブ中反応させると1-アダマンタンカルボン酸を転化率75%、選択率56%で得ることができた。本カルボキシル化反応の特徴は、まず第一に触媒的に達成された初めてのラジカルカルボキシル化反応であること、また従来のカルボキシル化反応と比べ格段に収率が改善された点等が上げられる。他のアルカン類への拡張を試みたところ、第三級水素を含むポリ環状アルカン類からは同様なカルボキシル化が期待できることがわかった。さらに、アダマンタンを一酸化炭素の代わりに2,3-ブタンジオンを用いて反応を試みたところ、ラジカル触媒的なアセチル化が達成され1-アセチルアダマンタンを収率よく得られることがわかった。
    これらの結果は、これまで行われてきたカルボキシル化やアセチル化に比べ反応条件や反応の選択性など大幅に凌駕し、新しい触媒的ラジカル発生法として注目されるものである。

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  • セレン-金属結合の特性を生かした新規合成反応の開拓

    Grant number:09239250  1997

    日本学術振興会  科学研究費助成事業  重点領域研究

    西山 豊

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    Grant amount:\2000000 ( Direct Cost: \2000000 )

    第16族に属するセレンは種々の原子価状態を取り、また、セレン原子を分子内に有するフェニルセレノ(PhSe)基はそのα-位のアニオン、カチオンいずれも安定化するなどの特性を有している。それらのセレン化合物の特性と他の金属化合物の特性を合わせ持つ化合物を合成し、それら二つの特性を効率良く利用できれば、今までとは異なった新しいタイプの反応が開発できるものと期待される。そこで種々のセレン-メタル結合を有する化合物を合成し、それら化合物と種々の有機化合物の反応を検討することでそれら化合物特有の反応を見いだすことを目的とし研究を行った。
    その結果、セレン-金属結合として、セレン-スズ結合を有するトリブチルスタニルフェニールセレノレート(PhSeSnBu_3)を用いルイス酸存在下エポキシドとの反応を行ったところ、高収率かつ高い位置選択的でエポキシドの開環反応が進行し、β-ヒドロキシフェニールセレニドの効率良い合成法となりえることを見い出した。特に従来の有機セレン試剤では高い位置選択性で反応を進行させることが困難とされるスチレンオキシドを用いた際にも高い位置選択性で反応は進行する。一方セレン-金属結合として、セレン-アルミニウム結合を有するPhSeAlBu_2^iを用いた反応では、アルキンの炭素-炭素三重結合に対しPhSeAlBu_2^iが無触媒条件下で付加反応を起こし、さらに連続して種々の反応剤を加えることで種々の官能基を有するビニルセレニドが得られることから、本反応がビニルセレニドの新規合成法として利用可能であることを見い出した。

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  • Development of oxidation system with molecular oxygen catalyzed by N-hydroxyphthalimide (NHPI)

    Grant number:08455420  1996 - 1997

    Japan Society for the Promotion of Science  Grants-in-Aid for Scientific Research  Grant-in-Aid for Scientific Research (B)

    ISHII Yasutaka, SAKAGUCHI Satoshi, NISHIYAMA Yutaka

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    Grant amount:\5400000 ( Direct Cost: \5400000 )

    N-Hydroxyphthalimide (NHPI) was found to be an efficient catalyst for the aerobic oxidation of various alkanes to the corresponding oxygen-containing products such as alcohols, ketones, and carboxylic acids. The oxidation of cyclohexane catalyzed by NHPI combined with a trace amount of transion metal salt such as Mn (acaca)_2 produced adipic acid in good yield. Isobutane was also oxidized by the use of NHPI and Co (acac)_2 as catalyst to give t-butyl alcohol.
    Furthermore, the selective oxidation of alkylbenzenes such as toluene and xylene were successfully achieved under normal pressure and temperature. For instance, the oxidation of toluene with dioxygen in the presence of catalytic amount of NHPI and Co (OAc)_2 in acetic acid at room temperature for 20 h formed benzoic acid in 81% selectivity at 84% conversion. Although the oxidation of alkylbenzenes has been so far operated under relatively severe reaction conditions, higher temperature (150゜C) and oxygen (or air) pressure (5-10 atm), the NHPI-catalyzed oxidation system is expected to provide a new methodology in the oxidation processes and promises to enhance commercial potentialities by the achievement of oxidation under ambient conditions.

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  • サマリウム(II)錯体を触媒とする新規合成反応の開拓

    Grant number:08220265  1996

    日本学術振興会  科学研究費助成事業  重点領域研究

    石井 康敬, 西山 豊

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    Grant amount:\1900000 ( Direct Cost: \1900000 )

    ランタノイド化合物は典型金属や遷移金属にない多くの特徴を有し、それらの特性を利用した有機合成反応が広く研究されている。特に、サマリウム(II)種であるヨウ化サマリウム(SmI_2)を用いた合成反応が広く展開され、サマリウム(II)種でしか行えない多くの反応が見いだされている。しかしながら、サマリウム(II)種に基づく反応は、いずれもサマリウム試剤を化学量論量または過剰量用いる必要があり、サマリウム(II)を触媒的に活用した例となるとほとんど知られていない。そこで我々はサマリウム(II)の触媒的な利用を目的とし検討を行ない以下の反応を見い出した。
    1)サマリウム種がイミンのアルドール型縮合反応の触媒として働くことを見い出した。特に反応系中でα,β-不飽和イミンの生成と同時に副生するアミンをギ酸エステルまたはアルデヒドで捕捉することで、イミンのアルドール型縮合反応を効率良く進行し、対応するα,β-不飽和イミンが良好な収率で得られた。
    2)すでに1級、2級アルコールならびにアミン類の酢酸イソプロペニルによるアシル化をCp^*_2Sm(thf)_2が効率良く触媒することを見いだしているが、3級アルコールのアシル化に対しては十分に満足のいく結果は得られていなかった。そこで、二価のサマリウム種により炭素一窒素二重結合を効率良く活性化出来ることに着目し、オキシムエステルをアルコール類のアシル化剤として利用することを検討した。その結果、Cp^*_2Sm(thf)_2錯体存在下、オキシムエステルをアシル化剤として用いることで1、2級のみならず3級アルコールのアシル化反応を中性かつ温和な条件下効率良く促進できることを見いだした。

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  • サマリウム(II)種を用いた新規触媒反応の開拓

    Grant number:07230291  1995

    日本学術振興会  科学研究費助成事業  重点領域研究

    石井 康敬, 西山 豊

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    Grant amount:\2400000 ( Direct Cost: \2400000 )

    ランタノイド化合物は典型金属や遷移金属にない多くの特徴を有し、それらの特性を利用した有機合成反応が広く研究されている。特に、サマリウム(II)種であるヨウ化サマリウム(Sml_2)を用いた合成反応が広く展開され、サマリウム(II)種でしか行えない多くの反応が見いだされている。しかし、サマリウム(II)種に基づく反応は、いずれもサマリウム試剤を化学量論量または過剰量用いる必要があり、サマリウム(II)を触媒的に活用した例となるとほとんど知られていない。それゆえ、サマリウム(II)化合物がもつ特有の反応性を生かした触媒反応の開発が期待されている。
    そこで本研究では、サマリウム(II)を触媒に用いた新しい合成反応を開拓することを目的とし検討を行った。その結果、ペンタメチルシクロペンタジエニル基(Cp^*)を配位子とする2価のサマリウム種として比較的安定なCp^*_2Sm(thf)_2が酢酸ビニルとアルデヒドの1:2カップリング反応の効率良い触媒として働き、対応するジエステルが良好な収率で得られることを見い出した。一方Cp^*_2Sm(thf)_2触媒存在下、アルコールおよびアミンとビニルエステルの反応を検討したところ、対応するエステル、アミドが得られ、ビニルエステルがアルコールおよびアミド類のアシル化剤として利用可能であることが明らかとなった。またヨウ化サマリウム(II)を触媒としイミンをギ酸エステル存在下反応を行なうと、イミンがアルドール型縮合反応を起こしたα,β-不飽和イミンを生成することを見い出した。

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  • Aerobic Oxidation Catalyzed by Mixed Addenda Heteropolyoxometarates

    Grant number:06453143  1994 - 1995

    Japan Society for the Promotion of Science  Grants-in-Aid for Scientific Research  Grant-in-Aid for General Scientific Research (B)

    ISHII Yasutaka, NISHIYAMA Yutaka, HAMANAKA Sawako

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    Grant amount:\4600000 ( Direct Cost: \4600000 )

    Oxidations of variountaining vanadium and molybdenum were examined. In addition, the combination of Pd (II) with vanadomolybdophosphate (NPVMo) in the presence of hydroquinone was found to be an efficient catalytic system for the oxidation of alkenes with molecular oxygen. We have obtained the following results in this project.
    1. Oxidation of various organic substrates with molecular oxygen by NPVMo
    Vanadomolybdophosphate (NPVMo), which can be shown as (NH_4) _5H_6PV_4Mo_8O_<40>, catalyzed the oxidation of aromatic amines, benzyl alcohols and phenols to the corresponding imines, bezaldehydes and quinoes with molecular oxygen under relatively mild conditions.
    2. Development of indirect oxidation using molecular oxygen as final oxidant
    Hydroquinone was smoothly dehydrogenated with molecular oxygen to quinone by NPVMo. By combination of Pd (II) and this system, anew oxidation system has been developed. Thus, a variety of cycloalkenes such as cyclohexene underwent the acylation in acetic acid by Pd (II) /hydroquinone/NPVMo/O_2 system to form 3-acetoxy-1-cycloalkenes in quantitative yields. When ethyl acrylate and acrylonitrile was allowed to react in ehtanol by the use of this catalytic system, acetalization took place to form the corresponding acetals in good yields.
    3. Oxidation by the use of N-hydroxyphthalimide as catalyst
    N-Hydroxyphthalimide (NHPI) was found to catalyze the oxidation of benzylic compounds with molecular oxygen to give alcohols or ketones in fair yields. This catalytic oxidation was found to be a novel aerobic oxidation system. The oxidation of alkanes such as cyclohexane was achieved by NHPI in the presence of Co (acac) n (n=2 or 3). For example, cyclohexane was converted to cyclohexanone and adipic acid in fair yields. This method was extended to the aerobic oxidation of various organic substrates.

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  • ランタノイド金属/ハロシラン系から発生させた不安定化学種の利用

    Grant number:06241276  1994

    日本学術振興会  科学研究費助成事業  重点領域研究

    石井 康敬, 西山 豊

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    Grant amount:\2500000 ( Direct Cost: \2500000 )

    サマリウム/有機ハロシラン反応系を用いることにより、新規なSm(II)等価体の調製法を見いだし、本方法を用いることにより望ましい反応性ならびに還元力を持つ低原子価サマリウム種の調製に成功した。本研究では以下の点を明らかにした。
    (1)金属サマリウムとトリメチルクロロシラン(Me_3SiCl)/ヨウ化ナトリウム(NaI)反応剤またはトリメチルブロモシラン(Me_3SiBr)から調製したサマリウム(II)等価体の反応性を利用し種々のケトンやアルデヒド類の還元二量化反応を行ない、これまでHMPAを添加しないとピナコールカップリングが困難であった基質に対してもMe_3SiBr/Sm反応剤いることにより反応を効率よく進行させることができた。
    イミン類とα,β-不飽和エステルのカップリング反応がMe_3SiI/Sm反応剤を用いるよりもMe_3SiBr/Sm反応剤を用いると収率良く進行することがわかった。また、ケトン類とα,β-不飽和エステルより同様にして一段でラクトンが合成できることも明らかとなった。このようにハロシランを選ぶことにより生成する低原子価サマリウム種の反応性を制御でき、それぞれの反応に適したサマリウム種の調製が可能となった。
    (3)ジメチルクロロシラン(Me_3SiHCl)を金属サマリウムでもって処理すると、反応性の高い不安定ケイ素種が発生し、続いて微量のパラジウム触媒存在下末端アルキンを加えると好収率でヒドロシル化反応が起こることがわかった。この方法を用いると、パラジウム触媒のみでは困難な比較的不活性なクロロシラン類のヒドロシリル化反応が可能であることがわかった。また、サマリウム種は反応性の低い金属の活性化法として用いることができる。

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  • Development of Novel Synthetic Reaction Using Cycloalkanones

    Grant number:04555211  1992 - 1994

    Japan Society for the Promotion of Science  Grants-in-Aid for Scientific Research  Grant-in-Aid for Developmental Scientific Research (B)

    ISHII Yasutaka, NISHIYAMA Yutaka, TAMURA Rui

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    Grant amount:\5700000 ( Direct Cost: \5700000 )

    PGB_1 analogues with functionalized alpha-side chain have been synthesized in several steps from 1,3-cyclopentanedion. Introduction of alpha-and omega-side chains into the PGB_1 cyclopentenone skeltone has been accomplished by replacement reaction via stabilized carbanions. The substitution reaction with stabilized carbanion has been confirmed to process via a radical chain mechanism of S_<RN>1 type by the ESR studies. The PGB_1 thus obtained were subjected to the screening test for the biological activities. Among the PGB_1 synthesized in the present study, it was found that 6 samples of these act as insecticide of tick and rice insect. From the consideration of S_<RN>1 type reaction, it was found that a stable radical intermediate is formed in the course of this reaction.By using this methodology, we are able to confirm a general preparation method of cyclized nitroxy radicals bearing quarternary asymmetric carbon.
    On the other hand, the synthesis of 2,6-dialkylphenols which is difficult to prepare by conventional method is accomplished from the direct condensation reaction between cyclohexanone and aldehydes catalyzed by zirconocene complexes. The anti-oxidant property of the resulting phenols was compared with those of commercial avairable ones, and these were comparable or superier to comventinal phenol system of anti-oxidants. This method has been extended to the cyclopentenone synthesis from ketones and aldehydes, and esters by Tishchenko rection.

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  • 新規標識化合物の合成法の開発

    Grant number:04750722  1992

    日本学術振興会  科学研究費助成事業  奨励研究(A)

    西山 豊

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    Grant amount:\900000 ( Direct Cost: \900000 )

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  • The Organic Reactions and Synthesis based on the Utilization of Carbon Monoxide

    Grant number:02650615  1990 - 1992

    Japan Society for the Promotion of Science  Grants-in-Aid for Scientific Research  Grant-in-Aid for General Scientific Research (C)

    HAMANAKA Sawako, NISHIYAMA Yutaka

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    Grant amount:\2000000 ( Direct Cost: \2000000 )

    1. Synthesis utilization reducing ability of carbon monoxide, - Using CO/H_2O/Se reaction system-
    (1) In the reductive dibromination of vic-dibromoalkanes with CO and H_2O in the presence of a catalytic amount of Se, vic-dibromoalkanes were converted to the corresponding alkanes in good yields and stereospecific.
    (2) The selective generation of tertiary amine salts of hydrogen selenide and diselenide has been achived by controlling the reaction conditions. Diorganylselenides and diorganyldiselenides were synthesized in good yields with perfect selectivity.
    (3) Phenyl substituted alpha- and beta-diketones were reduced to corresponding aromatic ketones in moderate to good yields.
    2. Utilization of carbon monoxide as a useful agentas for introducing carbonyl functions into organic molecules.
    (1) Treatment of 1, 1- or 1, 2-diphenylalkanes in benzene with AlCl_3-HCl formed the red-oil involving a phenylalkylcarbocations. When carbon monoxide was introduced to the red-oil, the phenylalkylcarbocations reacted with carbon monoxide to give 2-disubstituted-1-indanones via cyclization of the resulting acylcation.
    (2) 1-adamantanecarboxaldehyde was synthesized by the AlI_3-catalyzed reaction of adamantane with CO in CH_2Cl_2 at < 25゜C

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Devising educational methods

  • 授業評価の定期的な実施(全担当科目、大学の指定した期間) オフェスアワーについては、随時、個人研究室で個別に対応 演習、実験科目では、TAを活用し、きめ細かい指導を心掛ける 演習科目の解答は、授業中に解説すると共に、インフォメーションシステムを利用して開示

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  • 新しい工業化学(化学同人)共著 Organic Experiments(関西大学出版)共著

Teaching method presentations

  • 高大連携プログラム(Kan-Dai1セミナー) 兵庫県立星陵高校(2006/10/27)、 大阪府立堺東高校(2007/1/24)、 兵庫県立御影高校(2010/9/10)、 兵庫県立西宮北高校(2011/7/28)を実施

Special notes on other educational activities

  • 三大学(関西大学、大阪医科大学、大阪薬科大学)医工薬連環科学シンポジウム(第3回)(2010.7.8)で講演