Updated on 2024/08/06

写真a

 
UMEDA,Rui
 
Organization
Faculty of Chemistry, Materials and Bioengineering Professor
Title
Professor
Contact information
メールアドレス
External link

Degree

  • 博士(工学)

Research Interests

  • 有機機能性材料

  • 共役π電子系;多環式芳香族化合物;有機機能性材料

  • 多環式芳香族化合物

  • 共役π電子系

Research Areas

  • Nanotechnology/Materials / Structural organic chemistry and physical organic chemistry

  • Nanotechnology/Materials / Synthetic organic chemistry

  • Nanotechnology/Materials / Organic functional materials

  • Life Science / Bioorganic chemistry

Education

  • Osaka University   Graduate School, Division of Engineering Science

    2006

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  • Osaka University   Graduate School, Division of Engineering Science

    2003

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  • Osaka University   Faculty of Engineering Science

    - 2001

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  • Kurume National College of Technology

    - 1999

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  • Osaka University   Graduate School, Division of Engineering Science

    2006

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  • Osaka University   Graduate School, Division of Engineering Science

    2003

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Professional Memberships

Papers

  • Rhenium-catalyzed Disproportionation of Allylic Alcohols and Selective Reduction of Allylic Alcohol with Secondary Alcohol Reviewed

    Y. Nishiyama, T. Yamamoto, S. Mori, R. Umeda

    Tetrahedron Lett.   2024, 134   154836   2024.1

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  • Rhenium-catalyzed Synthetic Method of 1,2-Dihydroisoquinolines and Isoquinolines by the Intramolecular Cyclization of 2-Alkynylaldimines or 2-Alkynylbenzylamines Reviewed

    R. Umeda, T. Ishida, S. Mori, H. Yashima, T. Yajima, I. Osaka, R. Takata, Y. Nishiyama

    Tetrahedron   2024, 154   133854   2023.9

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  • Synthesis and Photophysical Properties of Diethynylated Bibenzofuran and Bibenzofuran Derivatives Reviewed

    T. Hibino, R. Umeda

    Heterocycles   2023, 106, 734-741.   2023.3

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  • One-pot Synthesis of 1,2-Dihydronaphthalenes by Cu-Catalyzed Reaction of 2-(Alkynyl)benzaldehydes and Alcohols Reviewed

    R. Umeda, N. Kimura, S. Ishii, Y. Nishiyama

    Synlett   2023, 134   188 - 192   2023.3

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  • Rhenium Complex-Catalyzed N-Allylation and N-Benzylation of Amines with Alcohols Reviewed

    R. Umeda, S. Shimaoka, S. Mori, T. Takagishi, Y. Nishiyama

    Tetrahedron Lett.   2023, 119, 154412.   2023.2

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  • Rhenium Complex-catalyzed Deoxygenation and Silylation of Alcohols with Hydrosilane Reviewed

    Y. Nishiyama, S. Xu, Y. Hanatani, S. Tsuda, R. Umeda

    Tetrahedron Lett.   2022, 99   153839   2022.6

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    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 Reviewed

    R. Umeda, R. Ueda, T. Tanaka, A. Hayashi, M. Ikeshita, S. Suzuki, T. Naota, Y. Nishiyama

    Tetrahedron   2021, 79, 131872.   2020.12

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  • Synthesis and Physical Properties of π-Extended Molecules having p-Methylenequinone Unit Reviewed

    R. Umeda, M. Nakatsukasa, Y. Nishiyama

    Heterocycles   2020, 101, 318-327.   2019.7

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  • Facile and Practical Synthesis of π-Extended Oxepins by Benzannulation and Intramolecular Cyclization Reviewed

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

    Tetrahedron Lett.   2019, 60, 183-186.   2018.12

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  • Rhenium-Catalyzed α-Alkylation of Enol Acetates with Alcohols or Ethers Reviewed

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

    J. Organomet. Chem.   2018, 877, 92-101.   2018.9

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  • Rhenium Complex-Catalyzed Carbon-Carbon Formation of Alcohols and Organosilicon Compounds Reviewed

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

    Tetrahedron Lett.   2018, 59, 1121-1124.   2018.2

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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, Y. Nishiyama

    Chemistry Letters   2018, 47 ( 6 )   753 - 755   2018

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    Authorship:Lead author   Language:English   Publishing type:Research paper (scientific journal)   Publisher:Chemical Society of 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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  • Rhenium Complex-Catalyzed Meinwald Rearrangement Reactions of Oxirane, Tetrahedron Lett. 2017, 58, 2393-2395. Reviewed

    R. Umeda, M. Muraki, Y. Nakamura,, T. Tanaka, K. Kamiguchi, Y. Nishiyama

    Tetrahedron Lett.   2017, 58, 2393-2395.   2017.5

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

    R. Umeda, N. Ikeda, M. Ikeshita, K. Sumino, S. Nishimura, Y. Nishiyama

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

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    Authorship:Lead author   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 Reviewed

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

    2016, 89   110 - 112   2016

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    Authorship:Lead author, Corresponding author   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 Reviewed

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

    Synth. Commun.   2016, 46 ( 6 )   546 - 550   2016

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    Authorship:Lead author, Corresponding author   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

    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 Reviewed

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

    Heterocycles   2015, 91 ( 11 )   2172 - 2179   2015

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

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

    Rui Umeda, Hiromasa Tabata, Yoshito Tobe, Yutaka Nishiyama

    Chemistry Letters   43 ( 6 )   883 - 884   2014

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    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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  • Synthesis and Physical Properties of Zethrene Derivatives bearing Donor/Acceptor Substituents at 7,14-Positions Reviewed

    Org. Biomol. Chem.   2013, 11, 8256-8261.   2013.10

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

    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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  • Molecular Propellers Consisting of Dehydrobenzo[14]annulene Blade Reviewed

    Nobusue, Shunpei, Mukai, Yuichi, Fukumoto, Yo, Umeda, Rui, Tahara, Kazukuni, Sonoda, Motohiro, Tobe, Yoshito

    Chemistry A European Journal   18 ( 40 )   12814 - 12824   2012.10

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

    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 Reviewed

    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

    Rui Umeda, Takumi Yuasa, Namika Anahara, Yutaka Nishiyama

    JOURNAL OF ORGANOMETALLIC CHEMISTRY   696 ( 9 )   1916 - 1919   2011.5

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    The first example of the FBW rearrangement using of lanthanum metal and a catalytic amount of iodine was disclosed. When gem-diiodo-and gem-dibromoalkenes were treated with lanthanum metal in the presence of a catalytic amount of iodine, the reductive dehalogenation of these compounds smoothly proceeded to produce the corresponding alkynes in moderate to good yields. (C) 2011 Elsevier B.V. All rights reserved.

    DOI: 10.1016/j.jorganchem.2011.02.014

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  • PtCl2-Catalyzed Cyclization of o-Diethynylbenzene Derivatives Triggered by Intramolecular Nucleophilic Attack Reviewed

    Koji Miki, Hiroyuki Kuge, Rui Umeda, Motohiro Sonoda, Yoshito Tobe

    SYNTHETIC COMMUNICATIONS   41 ( 7 )   1077 - 1087   2011

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    [image omitted] PtCl2-catalyzed cyclization of o-diethynylbenzene derivatives bearing a hydroxyethyl group yielded naphthofuran derivatives by initial intramolecular cyclization of the hydroxy group to an activated ethynyl group followed by attack of the second ethynyl group to a vinylplatinum intermediate. When the ethynyl terminal is substituted by a hydroxypropyl group, not only homologous naphthodihydropyran but also indenylidenetetrahydrofuran derivatives were formed.

    DOI: 10.1080/00397911003797817

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

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

    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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  • Tetradehydrodinaphtho[10]annulene and its transformation into zethrene: A hitherto unknown dehydroannulene and a forgotten aromatic hydrocarbon Reviewed

    Rui Umeda, Daijiro Hibi, Koji Miki, Yoshito Tobe

    Pure and Applied Chemistry   82 ( 4 )   871 - 878   2010

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    Language:English   Publishing type:Research paper (international conference proceedings)  

    The synthesis and structural characterization of a hitherto unknown tetradehydro - dinaphtho[10]annulene, which had eluded isolation since attempts initiated during the late 1960s, was achieved. Moreover, the dehydroannulene was transformed into stable derivatives of zethrene, which was first reported in 1955, but forgotten for a long time. These molecules are substituted at the 7,14-positions and open the door to the zethrene family for potential application as optoelectronic materials. © 2010 IUPAC.

    DOI: 10.1351/PAC-CON-09-10-12

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

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

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

    Synlett   2010, 3089-3091. ( 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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  • Rhenium-Catalyzed Reaction of Carbonyl Compounds with Ketene Silyl Acetals Reviewed

    Nishiyama Yutaka, Kaiba Kenta, Umeda Rui

    Tetrahedron Lett.   793-795 (2010)   2009.12

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  • Cesium Carbonate-Catalyzed α-Phenylchalcogenation of Carbonyl Compounds with Diphenyl Dichalcogenide Reviewed

    Nishiyama Yutaka, Koguma Yuya, Tanaka Toshimasa, Umeda Rui

    Molecules   3367-3375 (2009)   2009.9

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  • Tetradehydrodinaphtho[10]annulene: A Hitherto Unknown Dehydroannulene and a Viable Precursor to Stable Zethrene Derivatives Reviewed

    Umeda Rui, Hibi Daijiro, Miki Koji, Tobe Yoshito

    Org. Lett.   4104-4106 (2009)   2009.7

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  • Selective Metallation of 3-Halothiophenes: Practical Methods for the Synthesis of 2-Bromo-3-formylthiophene Reviewed

    Motohiro Sonoda, Shoko Kinoshita, Thanh Luu, Hiroshi Fukuda, Koji Miki, Rui Umeda, Yoshito Tobe

    SYNTHETIC COMMUNICATIONS   39 ( 18 )   3315 - 3323   2009

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

    Selective lithiation of 3-bromothiophene was accomplished under controlled conditions without formation of undesired thienyllithium compounds. A thienyl Grignard reagent derived from 2-bromo-3-iodothiophene was transformed into 2-bromo-3-formylthiophene in high selectivity by formylation with dimethylformamide (DMF) at optimal reaction temperature.

    DOI: 10.1080/00397910902763904

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  • Formation of Naphthodithiophene Isomers by Flash Vacuum Pyrolysis of 1,6-Di(2-thienyl)- and 1,6-Di(3-thienyl)-1,5-hexadien-3-ynes Reviewed

    Umeda Rui, Fukuda Hiroshi, Miki Koji, Rahman, S. M. A, Sonoda Motohiro, Tobe Yoshito

    Compt. Rend., Chimie   378-384 (2009)   2008.11

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  • Ag-catalyzed stereoselective cyclohexadienyl transfer: A novel entry into arylphenylmethanols Reviewed

    Rui Umeda, Armido Studer

    ORGANIC LETTERS   10 ( 5 )   993 - 996   2008.3

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

    The letter describes a novel concept for the synthesis of biologically important arylphenylmethanols. Stereoselective cyclohexadienyl transfer from 1,4-cyclohexadienyltributyltin to various aromatic aldehydes using AgOTf/BINAP as a catalyst precursor provides 1,4-cyclohexadienylphenylmethanols that are readily oxidized to the corresponding arylphenylmethanols. Fifteen examples are presented.

    DOI: 10.1021/ol703080a

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  • Desymmetrization of 1,4-cyclohexadienyltriisopropoxysilane using copper catalysis Reviewed

    Rui Umeda, Armido Studer

    ORGANIC LETTERS   9 ( 11 )   2175 - 2178   2007.5

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    The first catalytic desymmetrization in the field of allylsilane chemistry is presented. Desymmetrization of cyclohexadienyltriisopropoxysilane is achieved using coppper catalysis. High diastereo- and enantioselectivities are obtained, and the product dienes are highly valuable building blocks for natural product synthesis.

    DOI: 10.1021/ol070689d

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  • Resonance Raman spectra of polyyne molecules C10H2 and C12H2 in solution

    Tomonari Wakabayashi, Hiroshi Tabata, Tatsuya Doi, Hiroyuki Nagayama, Koji Okuda, Rui Umeda, Ichiro Hisaki, Motohiro Sonoda, Yoshito Tobo, Toshie Minematsu, Kenro Hashimoto, Shinji Hayashi

    CHEMICAL PHYSICS LETTERS   433 ( 4-6 )   296 - 300   2007.1

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    Resonance Raman spectra of hydrogen-capped linear carbon molecules, polyynes H(-C equivalent to C-)(n)H (n = 5,6), were measured in n-hexane. For C10H2, the peaks at 2123 cm(-1) and 2017 cm(-1) were identified as the nu(3)(sigma(g)) and nu(4)(sigma(g)) modes in D-infinity h symmetry, respectively. For C12H2, the peaks of nu(3)(sigma(g)) at 2097 cm(-1) and nu(4) (sigma(g)) at 2053 cm(-1) were identified. The relative intensities of the first-order Stokes lines and their resonance enhancement are discussed in terms of the Franck-Condon overlap and resonance absorption relevant to the fully-allowed electronic transition of (1)Sigma(+)(u) <-> (Chi) over tilde (1)Sigma(+)(g). (c) 2006 Elsevier B.V. All rights reserved.

    DOI: 10.1016/j.cplett.2006.11.077

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  • Gas Phase Generation of Highly Reactive Hexatriyne-Bridged [6n]Paracyclophyne Reviewed

    Umeda, Rui, Morinaka, Takayoshi, Sonoda, Motohiro, Tobe, Yoshito

    The Journal of Organic Chemistry   70 ( 15 )   6133 - 6136   2005.7

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  • Size-selective Formation of C78 Fullerene from a Three-dimensional Polyyne Precursor Reviewed

    Tobe, Yoshito, Umeda, Rui, Sonoda, Motohiro, Wakabayashi, Tomonari

    Chemistry--A European Journal   11 ( 5 )   1603 - 1609   2005.2

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  • Expanded Radialenes with Bicyclo[4.3.1]decatriene Units: New Precursors to Cyclo[n]carbons Reviewed

    Tobe, Yoshito, Umeda, Rui, Iwasa, Naruhito, Sonoda, Motohiro

    Chemistry--A European Journal   9 ( 22 )   5549 - 5559   2003.11

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  • Synthesis and facile rearrangement of 10,10-dicarbonyl-substituted [4.3.1]propellane derivatives Reviewed

    Y Tobe, T Kusumoto, S Minakata, R Umeda, M Sonoda, K Naemura

    CHEMISTRY LETTERS   32 ( 4 )   398 - 399   2003.4

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    While an attempt to prepare 10, 10-diformyl [4.3.1]propella-1,4-diene was not successful owing to its facial skeletal rearrangement, the corresponding diacetyl derivative was isolated, which would serve as a useful precursor of carbene sources.

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  • Vinylidene to alkyne rearrangement to form polyynes: synthesis and photolysis of dialkynylmethylenebicyclo[4.3.1]deca-1,3,5-triene derivatives Reviewed

    Y Tobe, N Iwasa, R Umeda, M Sonoda

    TETRAHEDRON LETTERS   42 ( 32 )   5485 - 5488   2001.8

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

    Dialkynylmethylenebicyclo[4.3.1]deca-1,3,5-triene derivatives were synthesized as precursors to generate dialkynylvinylidenes by extrusion of an aromatic fragment, indane. Photolysis of the trienes gave linear polyynes as the major products produced by rearrangement of the vinylidenes, together with the isomerization products having a methylenecycloheptatriene moiety. (C) 2001 Elsevier Science Ltd. All rights reserved.

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Books

  • 古くて新しい芳香族化合物~有機エレクトロニクス材料への応用~

    梅田 塁( Role: Sole author)

    理工学と技術(関西大学理工学会誌) 

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  • ポリインの合成

    戸部 義人, 梅田 塁

    シーエムシー出版・(新材料・新素材シリーズ)電子共役系有機材料の創製・機能開発・応用 

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  • Cyclic Alkynes

    Tobe Yoshito, Umeda Rui

    Science of Synthesis 

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  • Ir触媒による光学活性アリルアミン合成

    梅田 塁, 西山 豊

    月刊化学(化学同人) 

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  • ミュンスター大学、Studer研究室での留学生活 [海外研究室レポート]

    梅田 塁( Role: Sole author)

    Organo Metallicニュース (近畿化学協会有機金属部会誌) 

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MISC

  • 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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    Language:Japanese  

    CiNii Books

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  • Approaches to size-selective formation of fullerenes by cyclization of highly reactive polyyne chains

    R Umeda, M Sonoda, T Wakabayashi, Y Tobe

    CHEMISTRY LETTERS   34 ( 12 )   1574 - 1579   2005.12

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    Language:English   Publishing type:Book review, literature introduction, etc.   Publisher:CHEMICAL SOC JAPAN  

    As an approach to size-selective formation of fullerenes, we developed a method based on the cyclization of reactive cyclic polyynes which were generated by [2+2] cycloreversion of [4.3.2] propellatriene units. This method was proven to work successfully for the first time for the formation of fullerene ions C-60(+) and C-60(-) in the gas phase. This protocol is useful for generation of a small three-dimensional carbon cluster ion C-36(-) and a large fullerene C-78(-), as well.

    DOI: 10.1246/cl.2005.1574

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Presentations

  • Kinetic Stabilization of Unstable Molecules by Highly Hindered π-System

    R. Umeda, Y. Nishiyama

    18th International Symposium on Novel Aromatic Compounds (ISNA-18)  2019.7 

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    Event date: 2019.7

    Venue:Sapporo Convention Center  

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  • ナフタレン構築反応を利用する分子設計の指針

    梅田 塁

    ヘテロ原子部会 平成30年度第3回懇話会  2019.1 

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    Event date: 2019.1

    Venue:大阪科学技術センター6階605号室  

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  • Synthesis and Photophysical Properties of Dicyanobisbenzodioxin

    H. Enomoto, R. Umeda, Y. Nishiyama

    The 14th International Kyoto Conference on New Aspects of Organic Chemistry (IKCOC-14)  2018.11 

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    Event date: 2018.11

    Venue:Rihga Royal Hotel Kyoto  

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  • Synthesis of Tetraarylethylene Derivatives by Benzannulation Reaction and Their Photophysical Properties

    Y. Miki, R. Umeda, Y. Nishiyama

    The 14th International Kyoto Conference on New Aspects of Organic Chemistry (IKCOC-14)  2018.11 

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    Event date: 2018.11

    Venue:Rihga Royal Hotel Kyoto  

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  • Benzannulation反応を利用した短段階拡張パイ電子系の創出

    梅田 塁

    構造有機化学若手研究者研究会 2017  2017.8 

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    Event date: 2017.8

    Venue:岡山理科大学 A1号館1階プレゼンテーションルーム  

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

    Y. Nishiyama, R. Umeda

    2016.6 

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  • Reaction of Benzanthrone with Metal Acetylide

    Y. Shimizu, T. Namba, 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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  • 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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  • Selective Synthesis of 1-Halonaphthalenes by Copper-catalyzed Benzannulation

    R. Ueda, T.Tanaka, 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 Regioselective Synthesis of Multiple Substituted Polycyclic Aromatic Compounds

    R. Umeda, Y. Nishiyama

    2014.7 

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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

    The Eighth International Symposium on Integrated Synthesis (ISIS-8)  2013.11 

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    Event date: 2013.11 - 2013.12

    Venue:Todaiji Temple Cultural Center  

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  • パイ電子が高密度に集積化したらせん分子の合成・構造・光学特性

    梅田 塁

    構造有機化学若手研究者 ミニシンポジウム2013  2013.9 

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    Event date: 2013.9

    Venue:北海道大学理学部7号館  

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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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  • 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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  • Oxidation of N,N-Diarylamines with Benzenseleninic Anhydride

    A. Yoshimura, R. Umeda, Y. Nishiyama

    2012.5 

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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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  • 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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  • 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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  • 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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  • 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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    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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    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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    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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    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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    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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    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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    Venue:Hawaii Convention Center, Honolulu, Hawai, USA  

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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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    Venue:Seaside Hotel Maiko Villa Kobe, Hyogo, Japan  

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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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  • Generation of Novel Aromatic Compounds by Controlled Reactions of Accumulated Alkynes

    Grant number:21106011  2009.7 - 2014.3

    Japan Society for the Promotion of Science  Grants-in-Aid for Scientific Research  Grant-in-Aid for Scientific Research on Innovative Areas (Research in a proposed research area)

    TOBE Yoshito, TAHARA Kazukuni, UMEDA Rui

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    Grant amount:\54860000 ( Direct Cost: \42200000 、 Indirect Cost:\12660000 )

    On the basis of the concept of "space-and-time-integration," we developed a methodology to synthesize selectively and effciently aromatic compounds, which are difficult to obtain by conventional synthetic methods, having novel structures and electronic properties by transannular and/or tandem cyclization reactions using highly reactive acetylenic substrates having closely located alkynyl groups. In addition, the reactive intermediates generated during the course of the reactions were furhter transformed into more elaborated products in some cases. The structures, physical properties, and optoelectronic applications of newly synthesized aromatic compounds were investigated including photovoltaic applications of some products.

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  • Synthesis of Zethrene Derivatives by Transannular Cyclization of Tetradehydrodinaphtho[10]annulene and their Physical Properties

    Grant number:21750046  2009 - 2010

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

    UMEDA Rui

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    Grant amount:\2730000 ( Direct Cost: \2100000 、 Indirect Cost:\630000 )

    The synthesis and structural characterization of hitherto unknown tetradehydrodinaphtho[10]annulene was achieved for the first time. Moreover, the dinaphtho[10]annulene was transformed smoothly into stable zethrene derivatives substituted at its 7,14-positions, showing that it serves as a good reservoir of zethrene derivatives. Optical and electrochemicalproperties of a disubstituted zethrene derivative are also investigated.

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  • Creation of Novel Molecules and Molecular Assemblies Utilizing Electronic and Structural Characteristics of Acetylene Derivatives

    Grant number:18205007  2006 - 2008

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

    TOBE Yoshito, HIROSE Keiji, TAHARA Kazukuni, DE SCHRYVER Frans C., DE FEYTER Steven, LEI Shengbin, UMEDA Rui, YAMAGUCHI Yui, FUJITA Takumi

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    Grant amount:\50440000 ( Direct Cost: \38800000 、 Indirect Cost:\11640000 )

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Devising educational methods

  • フレッシュマンゼミナール:1年生の講義であり、受講人数もグループ分けされているため少人数で授業を行うメリットを活かし、全員に質問・発表させるようにした。講義内容は、理系学生としては理解してほしいデータの評価の仕方について身近な問題を取り上げておこない、また環境問題やエネルギー問題についても取り上げた。 基礎化学実験:基礎的な物理・分析実験を通して、データの取り扱い方、結果に導く考え方、考察並びにレポートの作成について指導している。 応用化学実験II:有機合成に用いる、器具ならびに試薬の取り扱いに習熟させるだけでなく、成功・失敗といった短絡的な結果の評価ではなく、一つ一つのプロセスの意味が理解できるように指導している。また、授業で習う内容と絡めることにより、座学と実学とを有機的に結びつけられるように取り組んでいる。

Teaching materials

  • 基礎化学実験 関西大学出版部 2009/3 (改訂作業編集と分担執筆)

Teaching method presentations

  •  特になし

Special notes on other educational activities

  • 北陽中学校連携プログラムならびに小・中学生を対象としたサイエンスセミナーに協力