Updated on 2026/03/07

写真a

 
TSUTIMOTO TERUHISA
 
Organization
Undergraduate School School of Science and Technology Professor
Title
Professor
External link

Degree

  • Ph. D ( Tokyo Institute of Technology )

Research Areas

  • Nanotechnology/Materials / Synthetic organic chemistry

Papers

  • β-Selective Addition of Pyrroles to Electron-Deficient Alkenes in Both Catalytic and Stoichiometric Modes on B(C<sub>6</sub>F<sub>5</sub>)<sub>3</sub>

    Seina Sekine, Miho Kashiwa, Maho Kawakami, Takumi Sonoda, Arisa Ono, Teruhisa Tsuchimoto

    ACS Omega   10 ( 21 )   21510 - 21518   2025.5

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    Publishing type:Research paper (scientific journal)   Publisher:American Chemical Society (ACS)  

    DOI: 10.1021/acsomega.5c00371

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  • Inside front cover: Direct Suzuki–Miyaura cross-coupling of C(sp2)–B(dan) bonds: designed in pursuit of usability

    Organic Chemistry Frontiers   12 ( 13 )   3742 - 3742   2025

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    Publishing type:Research paper (scientific journal)   Publisher:Royal Society of Chemistry (RSC)  

    DOI: 10.1039/d5qo90052b

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  • Direct Suzuki–Miyaura cross-coupling of C(sp<sup>2</sup>)–B(dan) bonds: designed in pursuit of usability

    Hiroki Andoh, Ryo Nakagawa, Tatsuya Akutagawa, Eiko Katata, Teruhisa Tsuchimoto

    Organic Chemistry Frontiers   12 ( 13 )   3759 - 3774   2025

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    Publishing type:Research paper (scientific journal)   Publisher:Royal Society of Chemistry (RSC)  

    We developed practical reaction conditions and a procedure for the direct Suzuki–Miyaura cross-coupling of C(sp<sup>2</sup>)–B(dan) bonds.

    DOI: 10.1039/d5qo00230c

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  • Quaternary Ammonium Salts: Catalysts for Hydrosilylation of Alkynes with Hydrosilanes

    Hiroki Andoh, Kosuke Nakamura, Yusuke Nakazawa, Tomoko Ikeda-Fukazawa, Satoki Okabayashi, Teruhisa Tsuchimoto

    Advanced Synthesis and Catalysis   365 ( 24 )   4583 - 4594   2023.12

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    Publishing type:Research paper (scientific journal)  

    DOI: 10.1002/adsc.202300423

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  • Cover Picture: Quaternary Ammonium Salts: Catalysts for Hydrosilylation of Alkynes with Hydrosilanes (Adv. Synth. Catal. 24/2023)

    Hiroki Andoh, Kosuke Nakamura, Yusuke Nakazawa, Tomoko Ikeda‐Fukazawa, Satoki Okabayashi, Teruhisa Tsuchimoto

    Advanced Synthesis &amp; Catalysis   365 ( 24 )   4318 - 4318   2023.11

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    Publishing type:Research paper (scientific journal)   Publisher:Wiley  

    DOI: 10.1002/adsc.202301235

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  • Discussion Addendum for: Indium‐Catalyzed Heteroaryl–Heteroaryl Bond Formation through Nucleophilic Aromatic Substitution: Preparation of 2‐Methyl-3-(thien-2‐yl)‐1H-indole

    Teruhisa Tsuchimoto

    Organic Syntheses   100   287 - 303   2023

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    Publishing type:Research paper (scientific journal)   Publisher:Organic Syntheses  

    DOI: 10.15227/orgsyn.100.0287

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  • Stepwise Suzuki−Miyaura Cross‐Coupling of Triborylalkenes Derived from Alkynyl−B(dan)s: Regioselective and Flexible Synthesis of Tetrasubstituted Alkenes Invited Reviewed

    Tomohiro Tani, Naomi Takahashi, Yuuki Sawatsugawa, Mana Osano, Teruhisa Tsuchimoto

    Advanced Synthesis & Catalysis   363 ( 9 )   2427 - 2442   2021.4

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    Authorship:Last author, Corresponding author   Publishing type:Research paper (scientific journal)   Publisher:Wiley  

    DOI: 10.1002/adsc.202001116

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    Other Link: https://onlinelibrary.wiley.com/doi/full-xml/10.1002/adsc.202001116

  • In(ONf)3-catalyzed 7-membered carbon-ring-forming annulation of heteroarylindoles with α,β-unsaturated carbonyl compounds Reviewed

    Teruhisa Tsuchimoto, Takahiro Johshita, Kazuhiro Sambai, Naoki Saegusa, Takumi Hayashi, Tomohiro Tani, Mana Osano

    Organic Chemistry Frontiers   8 ( 12 )   2882 - 2892   2021

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    <p>We developed the two recipes, on the indium-catalyzed reductive and oxidative 7-membered carbon-ring-forming annulations of heteroarylindoles with a,β-unsaturated carbonyl compounds.</p>

    DOI: 10.1039/d1qo00050k

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  • Front cover: In(ONf)3-catalyzed 7-membered carbon-ring-forming annulation of heteroarylin- doles with α,β-unsaturated carbonyl compounds

    Teruhisa Tsuchimoto, Takahiro Johshita Kazuhiro Sambai, Naoki Saegusa, Takumi Hayashi, Tomohiro Tani and Mana Osano

    Organic Chemistry Frontiers   8 ( 12 )   2867 - 2867   2021

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    <p>We developed the two recipes, on the indium-catalyzed reductive and oxidative 7-membered carbon-ring-forming annulations of heteroarylindoles with a,β-unsaturated carbonyl compounds.</p>

    DOI: 10.1039/d1qo90050a

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  • Front Cover Picture: Zinc/Indium Bimetallic Lewis Acid Relay Catalysis for Dehydrogenative Silylation/Hydrosilylation Reaction of Terminal Alkynes with Bis(hydrosilane)s (Adv. Synth. Catal. 19/2020)

    Tomohiro Tani, Yudai Sohma, Teruhisa Tsuchimoto

    Advanced Synthesis & Catalysis   362 ( 19 )   3925 - 3925   2020.10

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    DOI: 10.1002/adsc.202000968

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    Other Link: https://onlinelibrary.wiley.com/doi/full-xml/10.1002/adsc.202000968

  • Zinc/Indium Bimetallic Lewis Acid Relay Catalysis for Dehydrogenative Silylation/Hydrosilylation Reaction of Terminal Alkynes with Bis(hydrosilane)s Reviewed

    Tomohiro Tani, Yudai Sohma, Teruhisa Tsuchimoto

    Advanced Synthesis & Catalysis   362 ( 19 )   4098 - 4108   2020.10

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    DOI: 10.1002/adsc.202000501

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    Other Link: https://onlinelibrary.wiley.com/doi/full-xml/10.1002/adsc.202000501

  • Direct Suzuki–Miyaura Coupling with Naphthalene-1,8-diaminato (dan)-Substituted Organoborons Reviewed

    Hiroto Yoshida, Michinari Seki, Shintaro Kamio, Hideya Tanaka, Yuki Izumi, Jialun Li, Itaru Osaka, Manabu Abe, Hiroki Andoh, Tomoki Yajima, Tomohiro Tani, Teruhisa Tsuchimoto

    ACS Catalysis   10 ( 1 )   346 - 351   2020.1

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    DOI: 10.1021/acscatal.9b03666

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  • A Drastic Effect of TEMPO in Zinc‐Catalyzed Stannylation of Terminal Alkynes with Hydrostannanes via Dehydrogenation and Oxidative Dehydrogenation Reviewed

    Yuichi Kai, Shinya Oku, Tomohiro Tani, Kyoko Sakurai, Teruhisa Tsuchimoto

    Advanced Synthesis & Catalysis   361 ( 18 )   4314 - 4323   2019.9

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    Authorship:Last author, Corresponding author   Publishing type:Research paper (scientific journal)   Publisher:Wiley  

    DOI: 10.1002/adsc.201900540

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    Other Link: https://onlinelibrary.wiley.com/doi/full-xml/10.1002/adsc.201900540

  • Cover Picture: Alkylation of Terminal Alkynes under Zinc Lewis Acid Catalysis and Its Mechanistic Studies (Adv. Synth. Catal. 12/2019)

    Mana Osano, Takeru Kida, Kyohei Yonekura, Teruhisa Tsuchimoto

    Advanced Synthesis & Catalysis   361 ( 12 )   2736 - 2736   2019.6

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    DOI: 10.1002/adsc.201900598

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    Other Link: https://onlinelibrary.wiley.com/doi/full-xml/10.1002/adsc.201900598

  • Alkylation of Terminal Alkynes under Zinc Lewis Acid Catalysis and Its Mechanistic Studies Reviewed

    Mana Osano, Takeru Kida, Kyohei Yonekura, Teruhisa Tsuchimoto

    Advanced Synthesis & Catalysis   361 ( 12 )   2825 - 2831   2019.6

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    Authorship:Last author, Corresponding author   Publishing type:Research paper (scientific journal)   Publisher:Wiley  

    DOI: 10.1002/adsc.201801685

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    Other Link: https://onlinelibrary.wiley.com/doi/full-xml/10.1002/adsc.201801685

  • Front Cover Picture: Alkynyl−B(dan)s in Various Palladium‐Catalyzed Carbon−Carbon Bond‐Forming Reactions Leading to Internal Alkynes, 1,4‐Enynes, Ynones, and Multiply Substituted Alkenes (Adv. Synth. Catal. 8/2019)

    Tomohiro Tani, Yuuki Sawatsugawa, Yusuke Sano, Yo Hirataka, Naomi Takahashi, Sadahiro Hashimoto, Tetsuya Sugiura, Teruhisa Tsuchimoto

    Advanced Synthesis & Catalysis   361 ( 8 )   1699 - 1699   2019.4

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    DOI: 10.1002/adsc.201900239

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    Other Link: https://onlinelibrary.wiley.com/doi/full-xml/10.1002/adsc.201900239

  • Alkynyl−B(dan)s in Various Palladium‐Catalyzed Carbon−Carbon Bond‐Forming Reactions Leading to Internal Alkynes, 1,4‐Enynes, Ynones, and Multiply Substituted Alkenes Reviewed

    Tomohiro Tani, Yuuki Sawatsugawa, Yusuke Sano, Yo Hirataka, Naomi Takahashi, Sadahiro Hashimoto, Tetsuya Sugiura, Teruhisa Tsuchimoto

    Advanced Synthesis & Catalysis   361 ( 8 )   1815 - 1834   2019.4

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    DOI: 10.1002/adsc.201801527

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    Other Link: https://onlinelibrary.wiley.com/doi/full-xml/10.1002/adsc.201801527

  • A Heteroarylamine Library: Indium-Catalyzed Nucleophilic Aromatic Substitution of Alkoxyheteroarenes with Amines Reviewed

    Kyohei Yonekura, Yasuhiro Yoshimura, Mizuri Akehi, Teruhisa Tsuchimoto

    Advanced Synthesis and Catalysis   360 ( 6 )   1159 - 1181   2018.3

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    Authorship:Last author, Corresponding author   Language:English   Publishing type:Research paper (scientific journal)   Publisher:Wiley-VCH Verlag  

    DOI: 10.1002/adsc.201701452

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  • Indium-Catalyzed Annulation of o-Acylanilines with Alkoxyheteroarenes: Synthesis of Heteroaryl[b]quinolines and Subsequent Transformation to Cryptolepine Derivatives Invited Reviewed

    Kyohei Yonekura, Mika Shinoda, Yuko Yonekura, Teruhisa Tsuchimoto

    Molecules   23 ( 4 )   838;1 - 18   2018

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    Authorship:Last author, Corresponding author   Language:English   Publishing type:Research paper (scientific journal)   Publisher:MDPI AG  

    DOI: 10.3390/molecules23040838

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  • Zinc-Catalyzed Dehydrogenative Silylation of Indoles Reviewed

    Kyohei Yonekura, Yoshihiko Iketani, Masaru Sekine, Tomohiro Tani, Fumiya Matsui, Daiki Kamakura, Teruhisa Tsuchimoto

    ORGANOMETALLICS   36 ( 17 )   3234 - 3249   2017.9

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    DOI: 10.1021/acs.organomet.7b00382

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  • Indium-Catalyzed Regioselective beta-Alkylation of Pyrroles with Carbonyl Compounds and Hydrosilanes and Its Application to Construction of a Quaternary Carbon Center with a beta-Pyrrolyl Group Reviewed

    Shota Nomiyama, Takahiro Ogura, Hiroaki Ishida, Kazuki Aoki, Teruhisa Tsuchimoto

    JOURNAL OF ORGANIC CHEMISTRY   82 ( 10 )   5178 - 5197   2017.5

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    DOI: 10.1021/acs.joc.7b00446

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  • Naked d-orbital in a centrochiral Ni(II) complex as a catalyst for asymmetric [3+2] cycloaddition Reviewed

    Yoshihiro Sohtome, Genta Nakamura, Atsuya Muranaka, Daisuke Hashizume, Sylvain Lectard, Teruhisa Tsuchimoto, Masanobu Uchiyama, Mikiko Sodeoka

    NATURE COMMUNICATIONS   8   14875;1 - 10   2017.4

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

    DOI: 10.1038/ncomms14875

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  • Indium-Catalyzed Formal N-Arylation and N-Alkylation of Pyrroles with Amines Reviewed

    Kyohei Yonekura, Kenji Oki, Teruhisa Tsuchimoto

    ADVANCED SYNTHESIS & CATALYSIS   358 ( 18 )   2895 - 2902   2016.9

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    Authorship:Last author, Corresponding author   Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.1002/adsc.201600656

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  • Easy Access to a Library of Alkylindoles: Reductive Alkylation of Indoles with Carbonyl Compounds and Hydrosilanes under Indium Catalysis Reviewed

    Shota Nomiyama, Takehiro Hondo, Teruhisa Tsuchimoto

    ADVANCED SYNTHESIS & CATALYSIS   358 ( 7 )   1136 - 1149   2016.3

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    Authorship:Last author, Corresponding author   Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.1002/adsc.201500502

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  • Carboxylative cyclization of propargylic amines with CO2 catalyzed by dendritic N-heterocyclic carbene-gold(I) complexes Reviewed

    Ken-ichi Fujita, Kensuke Inoue, Junichi Sato, Teruhisa Tsuchimoto, Hiroyuki Yasuda

    TETRAHEDRON   72 ( 9 )   1205 - 1212   2016.3

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

    DOI: 10.1016/j.tet.2016.01.016

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  • Alkynylboranes: A Practical Approach by Zinc-Catalyzed Dehydrogenative Coupling of Terminal Alkynes with 1,8-Naphthalenediaminatoborane Reviewed

    Teruhisa Tsuchimoto, Hirokazu Utsugi, Tetsuya Sugiura, Shin Horio

    ADVANCED SYNTHESIS & CATALYSIS   357 ( 1 )   77 - 82   2015.1

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    Authorship:Last author, Corresponding author   Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.1002/adsc.201400767

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  • Metal-Free Regioselective beta-Alkylation of Pyrroles with Carbonyl Compounds and Hydrosilanes: Use of a Bronsted Acid as a Catalyst Reviewed

    Shota Nomiyama, Teruhisa Tsuchimoto

    ADVANCED SYNTHESIS & CATALYSIS   356 ( 18 )   3881 - 3891   2014.12

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    Authorship:Last author, Corresponding author   Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.1002/adsc.201400497

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  • RE12 derivatives displaying Vaccinia H1-related phosphatase (VHR) inhibition in the presence of detergent and their anti-proliferative activity against HeLa cells Reviewed

    Frederic Thuaud, Shuntaro Kojima, Go Hirai, Kana Oonuma, Ayako Tsuchiya, Takako Uchida, Teruhisa Tsuchimoto, Mikiko Sodeoka

    BIOORGANIC & MEDICINAL CHEMISTRY   22 ( 9 )   2771 - 2782   2014.5

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

    DOI: 10.1016/j.bmc.2014.03.012

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  • Aqueous media carboxylative cyclization of propargylic amines with CO2 catalyzed by amphiphilic dendritic N-heterocyclic carbene-gold(I) complexes Reviewed

    Ken-ichi Fujita, Junichi Sato, Kensuke Inoue, Teruhisa Tsuchimoto, Hiroyuki Yasuda

    TETRAHEDRON LETTERS   55 ( 19 )   3013 - 3016   2014.5

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    DOI: 10.1016/j.tetlet.2014.03.074

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  • Indium-catalyzed heteroaryl–heteroaryl bond formation through nucleophilic aromatic substitution: preparation of 2-methyl-3-(thien-2-yl)-1H-indole Reviewed

    Nagase, Y, Tsuchimoto, T

    Org. Synth.   91   273 - 282   2014.3

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  • Zinc-Catalyzed Direct Cyanation of Indoles and Pyrroles: Nitromethane as a Source of a Cyano Group Reviewed

    Yuta Nagase, Tetsuya Sugiyama, Shota Nomiyama, Kyohei Yonekura, Teruhisa Tsuchimoto

    ADVANCED SYNTHESIS & CATALYSIS   356 ( 2-3 )   347 - 352   2014.2

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    DOI: 10.1002/adsc.201301073

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  • Indium-catalyzed Annulation of Indoles with Ethyl (2-Ethynylaryl)methyl Carbonates: Synthesis and Photo luminescent Properties of Aryl- and Heteroaryl[b]carbazoles Reviewed

    Yuta Nagase, Takuhiro Miyamura, Kensuke Inoue, Teruhisa Tsuchimoto

    CHEMISTRY LETTERS   42 ( 10 )   1170 - 1172   2013.10

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

    DOI: 10.1246/cl.130402

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  • Indium-catalyzed annulation of 3-aryl- and 3-heteroarylindoles with propargyl ethers: synthesis and photoluminescent properties of aryl- and heteroaryl[c]carbazoles Reviewed

    Yuta Nagase, Hiroyuki Shirai, Masayoshi Kaneko, Eiji Shirakawa, Teruhisa Tsuchimoto

    ORGANIC & BIOMOLECULAR CHEMISTRY   11 ( 9 )   1456 - 1459   2013

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    Authorship:Last author, Corresponding author   Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.1039/c3ob27407a

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  • Homogeneous Dihydroxylation of Olefins Catalyzed by OsO42- Immobilized on a Dendritic Backbone with a Tertiary Nitrogen at Its Core Position Reviewed

    Ken-ichi Fujita, Kensuke Inoue, Teruhisa Tsuchimoto, Hiroyuki Yasuda

    CHEMICAL & PHARMACEUTICAL BULLETIN   60 ( 12 )   1594 - 1598   2012.12

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

    DOI: 10.1248/cpb.c12-00682

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  • Dehydrogenative Silylation of Terminal Alkynes with Hydrosilanes under Zinc-Pyridine Catalysis Reviewed

    Teruhisa Tsuchimoto, Masakazu Fujii, Yoshihiko Iketani, Masaru Sekine

    ADVANCED SYNTHESIS & CATALYSIS   354 ( 16 )   2959 - 2964   2012.11

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    DOI: 10.1002/adsc.201200310

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  • Zinc-Catalyzed Dehydrogenative N-Silylation of Indoles with Hydrosilanes Reviewed

    Teruhisa Tsuchimoto, Yoshihiko Iketani, Masaru Sekine

    CHEMISTRY-A EUROPEAN JOURNAL   18 ( 31 )   9500 - 9504   2012.7

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    DOI: 10.1002/chem.201200651

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  • Development of New Catalytic Reactions Based on Activation of Hydrocarbon Functional Groups by Lewis Acids

    Teruhisa Tsuchimoto

    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN   69 ( 8 )   889 - 903   2011.8

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    Language:Japanese   Publishing type:Research paper (scientific journal)  

    DOI: 10.5059/yukigoseikyokaishi.69.889

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  • Catalytic Asymmetric alpha-Chlorination of 3-Acyloxazolidin-2-one with a Trinary Catalytic System

    Yoshitaka Hamashima, Tatsuya Nagi, Ryo Shimizu, Teruhisa Tsuchimoto, Mikiko Sodeoka

    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY   ( 20-21 )   3675 - 3678   2011.7

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    DOI: 10.1002/ejoc.201100453

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  • Magnetically recoverable osmium catalysts for dihydroxylation of olefins

    Ken-ichi Fujita, Satoshi Umeki, Manabu Yamazaki, Taku Ainoya, Teruhisa Tsuchimoto, Hiroyuki Yasuda

    TETRAHEDRON LETTERS   52 ( 24 )   3137 - 3140   2011.6

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    DOI: 10.1016/j.tetlet.2011.04.030

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  • Selective Synthesis of beta-Alkylpyrroles

    Teruhisa Tsuchimoto

    CHEMISTRY-A EUROPEAN JOURNAL   17 ( 15 )   4064 - 4075   2011.4

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    DOI: 10.1002/chem.201002248

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  • Reductive Alkylation of Indoles with Alkynes and Hydrosilanes under Indium Catalysis

    Teruhisa Tsuchimoto, Mitsutaka Kanbara

    ORGANIC LETTERS   13 ( 5 )   912 - 915   2011.3

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    DOI: 10.1021/ol1029673

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  • Microwave-assisted organic functionalization of silica surfaces: Effect of selectively heating silylating agents

    Norihisa Fukaya, Hiroshi Yamashita, Hisato Haga, Teruhisa Tsuchimoto, Syun-ya Onozawa, Toshiyasu Sakakura, Hiroyuki Yasuda

    JOURNAL OF ORGANOMETALLIC CHEMISTRY   696 ( 4 )   825 - 828   2011.2

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    DOI: 10.1016/j.jorganchem.2010.10.008

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  • Indium-Catalyzed Heteroaryl-Heteroaryl Bond Formation through Nucleophilic Aromatic Substitution

    Teruhisa Tsuchimoto, Mami Iwabuchi, Yuta Nagase, Kenji Oki, Hiroshi Takahashi

    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION   50 ( 6 )   1375 - 1379   2011

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    DOI: 10.1002/anie.201005750

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  • Organic functionalization of the surface of silica with arylsilanes. A new method for synthesizing organic-inorganic hybrid materials

    Norihisa Fukaya, Hisato Haga, Teruhisa Tsuchimoto, Syun-ya Onozawa, Toshiyasu Sakakura, Hiroyuki Yasuda

    JOURNAL OF ORGANOMETALLIC CHEMISTRY   695 ( 23 )   2540 - 2542   2010.11

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    DOI: 10.1016/j.jorganchem.2010.08.023

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  • A recyclable dendritic osmium catalyst for homogeneous dihydroxylation of olefins

    Ken-ichi Fujita, Manabu Yamazaki, Taku Ainoya, Teruhisa Tsuchimoto, Hiroyuki Yasuda

    TETRAHEDRON   66 ( 44 )   8536 - 8543   2010.10

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    DOI: 10.1016/j.tet.2010.08.062

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  • Development of innovative one-step synthesis of .beta.-alkylpyrroles

    Meiji Daigaku Kagaku Gijyutsu Kenkyusho Nenpo   50   68-69   2010.3

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  • Homogeneous dihydroxylation of olefins catalyzed by a recyclable OsO42- core dendrimer

    Ken-ichi Fujita, Taku Ainoya, Teruhisa Tsuchimoto, Hiroyuki Yasuda

    TETRAHEDRON LETTERS   51 ( 5 )   808 - 810   2010.2

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    DOI: 10.1016/j.tetlet.2009.11.126

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  • Exclusive Synthesis of beta-Alkylpyrroles under Indium Catalysis: Carbonyl Compounds as Sources of Alkyl Groups

    Teruhisa Tsuchimoto, Motohiro Igarashi, Kazuki Aoki

    CHEMISTRY-A EUROPEAN JOURNAL   16 ( 30 )   8975 - 8979   2010

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    DOI: 10.1002/chem.201000733

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  • Indium-Catalyzed Reductive Alkylation of Pyrroles with Alkynes and Hydrosilanes: Selective Synthesis of beta-Alkylpyrroles

    Teruhisa Tsuchimoto, Tatsuya Wagatsuma, Kazuki Aoki, Jun Shimotori

    ORGANIC LETTERS   11 ( 10 )   2129 - 2132   2009.5

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    DOI: 10.1021/ol900651u

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  • Synthesis of Methanes Having Four Different Carbon Substituents Utilizing Indium-Catalyzed Cleavage of Carbon-Pyrrolyl Bonds

    Teruhisa Tsuchimoto, Taku Ainoya, Kazuki Aoki, Tatsuya Wagatsuma, Eiji Shirakawa

    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY   ( 15 )   2437 - 2440   2009.5

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    DOI: 10.1002/ejoc.200900246

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  • Indium-Catalyzed Annulation of 2-Aryl- and 2-Heteroarylindoles with Propargyl Ethers: Concise Synthesis and Photophysical Properties of Diverse Aryl- and Heteroaryl-Annulated[a]carbazoles

    Teruhisa Tsuchimoto, Hiromichi Matsubayashi, Masayoshi Kaneko, Yuta Nagase, Takuhiro Miyamura, Eiji Shirakawa

    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY   130 ( 47 )   15823 - 15835   2008.11

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

    DOI: 10.1021/ja803954e

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  • Lewis acid catalyzed addition of pyrazoles to alkynes: Selective synthesis of double and single addition products

    Teruhisa Tsuchimoto, Kazuki Aoki, Tatsuya Wagatsuma, Yuichi Suzuki

    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY   ( 23 )   4035 - 4040   2008.8

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    DOI: 10.1002/ejoc.200800353

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  • Direct coupling of N-H bond and H-C bond

    Organometallic News   ( 2 )   82   2008.5

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  • Stereochemistry in Lewis acid-catalyzed silylation of alcohols, silanols, and methoxysilanes with optically active methyl(1-naphthyl)phenylsilane

    Satoshi Shinke, Teruhisa Tsuchimoto, Yusuke Kawakami

    Silicon Chemistry   3 ( 5 )   243 - 249   2007.4

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    DOI: 10.1007/s11201-007-9026-y

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  • Ruthenium-catalyzed addition of terminal alkynes to alkynylstannanes with migration of the stannyl group

    Eiji Shirakawa, Kouji Nakayama, Ryotaro Morita, Teruhisa Tsuchimoto, Yusuke Kawakami, Toshiaki Matsubara

    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN   79 ( 12 )   1963 - 1976   2006.12

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    DOI: 10.1246/bcsj.79.1963

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  • Studies on carbon-carbon bond forming reactions utilizing activation of unsaturated hydrocarbons and heteroaromatic compounds by metal sulfonate catalysts

    Teruhisa Tsuchimoto

    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN   64 ( 7 )   752 - 765   2006.7

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    DOI: 10.5059/yukigoseikyokaishi.64.752

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  • Nickel-catalyzed addition of organoboronates to 1,2-dienes and the corresponding three-component reaction with an alkyne

    Go Takahashi, Eiji Shirakawa, Teruhisa Tsuchimoto, Yusuke Kawakami

    ADVANCED SYNTHESIS & CATALYSIS   348 ( 7-8 )   837 - 840   2006.5

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    DOI: 10.1002/adsc.200505445

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  • A simple catalyst system for the palladium-catalyzed coupling of aryl halides with terminal alkynes

    E Shirakawa, T Kitabata, H Otsuka, T Tsuchimoto

    TETRAHEDRON   61 ( 41 )   9878 - 9885   2005.10

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    DOI: 10.1016/j.tet.2005.07.099

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  • Indium-catalysed synthesis of aryl- and heteroaryl-annulated carbazoles: systematic inveatigation of their emission properties

    IUPAC OMCO-13 Abstracts Geneva   2005.7

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  • Synthesis of multisubstituted 1,3-butadienes using the ruthenium-catalysed double addition of trimethylsilyldiazomethane to alkynylboronates

    R Morita, E Shirakawa, T Tsuchimoto, Y Kawakami

    ORGANIC & BIOMOLECULAR CHEMISTRY   3 ( 7 )   1263 - 1268   2005

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    DOI: 10.1039/b501990g

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  • Easy access to aryl- and heteroaryl-annulated[a]carbazoles by the indium-catalyzed reaction of 2-arylindoles with propargyl ethers

    T Tsuchimoto, H Matsubayashi, M Kaneko, E Shirakawa, Y Kawakami

    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION   44 ( 9 )   1336 - 1340   2005

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    DOI: 10.1002/anie.200462280

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  • Alkynes as activators in the nickel-catalysed addition of organoboronates to aldehydes

    G Takahashi, E Shirakawa, T Tsuchimoto, Y Kawakami

    CHEMICAL COMMUNICATIONS   ( 11 )   1459 - 1461   2005

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    DOI: 10.1039/b417353h

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  • 'Synthetic strategy for functionalized polyacene atructure using nickel-catalyzed alkynylstannylation of 1,2-dienes'

    Trans. MRS-J.   29   pp93-96   2004.11

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  • Nickel-catalyzed acylstannylation and alkynylstannylation of 1,2-dienes

    Y Nakao, E Shirakawa, T Tsuchimoto, T Hiyama

    JOURNAL OF ORGANOMETALLIC CHEMISTRY   689 ( 23 )   3701 - 3721   2004.11

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    DOI: 10.1016/j.jorganchem.2004.07.037

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  • Ruthenium-catalyzed hydrogenation of alkynylstannanes with migration of the stannyl group

    E Shirakawa, R Morita, T Tsuchimoto, Y Kawakami

    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY   126 ( 42 )   13614 - 13615   2004.10

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    DOI: 10.1021/ja0458827

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  • Nickel-catalyzed tandem carbostannylation of alkynes and 1,2-dienes with alkynylstannanes

    E Shirakawa, Y Yamamoto, Y Nakao, S Oda, T Tsuchimoto, T Hiyama

    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION   43 ( 26 )   3448 - 3451   2004

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    DOI: 10.1002/anie.200353649

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  • Zirconium triflate catalyzed direct coupling reaction of lactams with heterocyclic arenes under atmospheric oxygen

    T Tsuchimoto, Y Ozawa, R Negoro, E Shirakawa, Y Kawakami

    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION   43 ( 32 )   4231 - 4233   2004

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    DOI: 10.1002/anie.200460429

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  • A p-phosphinophenolate ligand for the palladium-catalysed arylation of alkenes

    E Shirakawa, K Ishii, T Tsuchimoto

    CHEMICAL COMMUNICATIONS   ( 23 )   2752 - 2753   2004

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    DOI: 10.1039/b41125g

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  • Indium triflate-catalysed double addition of heterocyclic arenes to alkynes

    T Tsuchimoto, K Hatanaka, E Shirakawa, Y Kawakami

    CHEMICAL COMMUNICATIONS   ( 19 )   2454 - 2455   2003.10

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    DOI: 10.1039/b308319e

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  • Palladium-catalysed dimerization of vinylarenes using indium triflate as an effective co-catalyst

    T Tsuchimoto, S Kamiyama, R Negoro, E Shirakawa, Y Kawakami

    CHEMICAL COMMUNICATIONS   ( 7 )   852 - 853   2003

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    DOI: 10.1039/b301280h

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  • 'Synthesis of polycyclic compounds utilizing the nickel-catalysed alkynylstannylation of 1,2-dienes'

    'RSC Publishing, Chem. Commun.'   pp1962-1963   2002.8

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    DOI: 10.1039/b206240b

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  • Metal triflate-catalyzed addition of arenes to alkynes

    The 2nd JAIST-POSTEC joint symposium Abstracts   p30   2002.3

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  • Nickel-catalysed addition of organoboronates to 1,3-dienes

    E Shirakawa, G Takahashi, T Tsuchimoto, Y Kawakami

    CHEMICAL COMMUNICATIONS   ( 19 )   2210 - 2211   2002

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    DOI: 10.1039/b207185a

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  • 光学活性アミンを不斉源とする華麗な触媒的不斉合成反応

    土本晃久

    日本化学会   54 ( 12 )   1392 - 1392   2001.12

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  • Nickel-catalysed hydroarylation of alkynes using arylboron compounds: selective synthesis of multisubstituted arylalkenes and aryldienes

    E Shirakawa, G Takahashi, T Tsuchimoto, Y Kawakami

    CHEMICAL COMMUNICATIONS   ( 24 )   2688 - 2689   2001.12

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    DOI: 10.1039/b107866f

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  • Dimerization of alkenes catalyzes by a palladium-metal triflate system

    PostOMCO-11 Abstacts   p168   2001.7

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  • Transition metal-catalysed acylation of α,β-unsaturated carbonyl compounds with acylstannanes

    Eiji Shirakawa, Youko Yamamoto, Yoshiaki Nakao, Teruhisa Tsuchimoto, Tamejiro Hiyama

    Chemical Communications   1 ( 19 )   1926 - 1927   2001

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    DOI: 10.1039/b105832k

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  • Bronsted acid-catalyzed hydration of alkynes: A convenient route to diverse carbonyl compounds

    T Tsuchimoto, T Joya, E Shirakawa, Y Kawakami

    SYNLETT   ( 12 )   1777 - 1778   2000.12

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    DOI: 10.1055/s-2000-8707

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  • Friedel-Crafts alkenylation of arenes using alkynes catalysed by metal trifluoromethanesulfonates

    T Tsuchimoto, T Maeda, E Shirakawa, Y Kawakami

    CHEMICAL COMMUNICATIONS   ( 17 )   1573 - 1574   2000

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  • Friedel-Crafts alkenylation of arenes using alkynes catalysed by metal trifluoromethanesulfonates

    T Tsuchimoto, T Maeda, E Shirakawa, Y Kawakami

    CHEMICAL COMMUNICATIONS   ( 17 )   1573 - 1574   2000

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    DOI: 10.1039/b003702h

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  • Synthetic applications of ortho esters

    P Wipf, T Tsuchimoto, H Takahashi

    PURE AND APPLIED CHEMISTRY   71 ( 3 )   415 - 421   1999.3

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    DOI: 10.1351/pac199971030415

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  • Superacid-catalyzed reductive Friedel-Crafts reaction of arenes using arenecarbaldehyde acetals

    S Fukuzawa, T Tsuchimoto, T Hiyama

    JOURNAL OF ORGANIC CHEMISTRY   62 ( 1 )   151 - 156   1997.1

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    DOI: 10.1021/jo961897e

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  • Scandium(III) Triflate-Catalyzed Friedel-Crafts Alkylation Reactions

    Teruhisa Tsuchimoto, Kazuo Tobita, Tamejiro Hiyama, Shin-Ichi Fukuzawa

    Journal of Organic Chemistry   62 ( 20 )   6997 - 7005   1997

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    DOI: 10.1021/jo970599u

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  • Scandium(III) trifluoromethanesulfonate-catalysed reductive Friedel-crafts benzylation of aromatic compounds using arenecarbaldehydes and propane-1,3-diol

    T Tsuchimoto, T Hiyama, S Fukuzawa

    CHEMICAL COMMUNICATIONS   ( 20 )   2345 - 2346   1996.10

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    DOI: 10.1039/cc9960002345

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  • Samarium(II) triflate as a new reagent for the Grignard-type carbonyl addition reaction

    'ACS Publications, J. Org. Chem.'   61   pp5400-5405   1996.7

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    DOI: 10.1021/jo960260s

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  • Scandium (III) triflate catalyzed Friedel-Crafts alkylation with benzyl and allyl alcohols

    T Tsuchimoto, K Tobita, T Hiyama, SI Fukuzawa

    SYNLETT   ( 6 )   557 - &   1996.6

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    DOI: 10.1055/s-1996-5498

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  • Alkylation-annulation of halo esters with organometallic reagent/SmI2 couple leading to cycloalkanols: A facile cyclopropanol synthesis from a 3-halo ester

    S Fukuzawa, H Furuya, T Tsuchimoto

    TETRAHEDRON   52 ( 6 )   1953 - 1960   1996.2

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    DOI: 10.1016/0040-4020(95)01039-4

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  • DIRECT SYNTHESIS OF CHIRAL ACETALS FROM CARBONYL-COMPOUNDS AND CHIRAL DIOLS - SEQUENTIAL ONE-POT ASYMMETRIC SILYLCYANATION REACTION CATALYZED BY SCANDIUM(III) TRIFLATE

    S FUKUZAWA, T TSUCHIMOTO, T HOTAKA, T HIYAMA

    SYNLETT   ( 10 )   1077 - &   1995.10

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  • A FACILE CONVERSION OF SUBSTITUTED CYCLOBUTANONES TO CYCLOPENTANONES BY CH2I2/SMI2 SYSTEM

    S FUKUZAWA, T TSUCHIMOTO

    TETRAHEDRON LETTERS   36 ( 33 )   5937 - 5938   1995.8

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    DOI: 10.1016/0040-4039(95)01199-R

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  • A facile one-pot synthesis of chiral acetals and subsequent C-C bond forming reactions catalyzed by Ln(OTf)3

    IUPAC OMCO-8 Abstracts Santa Barbara   p205   1995.8

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  • YTTERBIUM TRIFLUOROMETHANESULFONATE MEDIATED CROSS-ALDOL REACTION BETWEEN KETONES AND ALDEHYDES

    S FUKUZAWA, T TSUCHIMOTO, T KANAI

    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN   67 ( 8 )   2227 - 2232   1994.8

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    DOI: 10.1246/bcsj.67.2227

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  • Preparation of samarium(II) triflate and it mediated Grignard-type reaction. In situ formation and reaction of new organosamarium reagents

    FUKUZAWA Shin-ichi, TSUCHIMOTO Teruhisa, KANAI Takeshi

    Chem.Lett.   1994 ( 11 )   pp1981-1984 - 1984   1994.8

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    Samarium(II) triflate was readily prepared by the reaction of samarium(III) triflate with <I>sec</I>-butyllithium at room temperature in THF. Its reducing ability was examined by pinacol coupling of carbonyl compounds. Sm(OTf)<SUB>2</SUB> mediated Grignard-type reaction in THF-HMPA effectively; alkylation and allylation of ketones or aldehydes by simple alkyl, allyl, and benzyl halides proceeded <I>via</I> organosamarium intermediates.

    DOI: 10.1246/cl.1994.1981

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  • SAMARIUM(II) DIIODIDE INDUCED INTRAMOLECULAR COUPLING REACTION OF HALOCETALS LEADING TO THE SYNTHESIS OF GAMMA-LACTONES

    S FUKUZAWA, T TSUCHIMOTO

    SYNLETT   ( 10 )   803 - 804   1993.10

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  • Samarium(II) diiodide induced intramolecular coupling reaction of haloacetals leading to synthesis of γ-lactones

    IUPAC OMCO-7 Abstracts   p107   1993.9

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Books

  • 第 2 版有機合成実験法ハンドブック

    ( Role: Joint author19.3.12 章 pp. 654-658)

    有機合成化学協会  2015.11 

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MISC

  • Synthesis and Activation of Chiral Acetals Using Lanthanide Trifrates

    FURUYA H., FUKUZAWA S., TSUCHIMOTO T., HIYAMA T.

    ( 28 )   312 - 313   1996.5

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Presentations

  • Exclusive synthesis of β-alkylpyrroles under indium catalysis

    14th Asian Chemical Congress (14ACC)  2011.9 

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  • 炭化水素官能基とルイス酸:炭素–炭素間結合の活性化を中心に

    理研シンポジウム・第 6 回有機合成化学のフロンティア  2011.7 

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  • ルイス酸による炭化水素の活性化を基軸とする新触媒反応の開発

    第 27 回有機合成化学セミナー  2010.9  有機合成化学協会

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  • ルイス酸による炭化水素の活性化を基軸とする新触媒反応の開発

    神戸大学界面科学セミナー  2010.9 

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  • 金属スルホナート触媒により活性化された炭素求電子種と芳香族複素環化合物の反応

    有機合成化学協会関西支部, 有機合成化学北陸セミナー講演予稿集, 石川, 依頼講演

    平成 16 年度有機合成化学北陸セミナー  2004.10 

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Awards

  • 有機合成化学奨励賞「研究課題:ルイス酸による炭化水素の活性化を基軸とする新触媒反応の開発」

    2010.2  

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Research Projects

  • B(dan) 基含有マルチボリルアルケンの網羅的合成と合成化学的活用に関する研究

    Grant number:23K04739  2023.4 - 2026.3

    日本学術振興会  科学研究費助成事業  基盤研究(C)

    土本 晃久

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    Grant amount:\4680000 ( Direct Cost: \3600000 、 Indirect Cost:\1080000 )

    本申請課題では,当研究室で多様なアルキンからの合成に成功した RCCB(dan) 1 (dan = 1,8-diaminonaphtyl) をプラットフォームとして活用し、同一分子内に同一のボリル基は含まない各種マルチボリルアルケンの,立体及び位置選択的な合成を網羅的に達成することを第一の目的とした。第二の目的は,合成した各種マルチボリルアルケンを位置選択的な炭素-炭素結合伸長反応を初めとする各種変換反応に活用し、多置換アルケンの自在合成を目指すこととした。2023年度は,まずは,第一の目的の実現に向け,実験をおこなった。
    hexyl-CC-B(dan) (1a, hexyl: ヘキシル基) に対してビスピナコラートジボロン [(pin)B-B(pin)] を銅触媒存在下に反応させると,(pin)B-B(pin) のうちの一つのボリル基が 1a の hexyl 基側,水素原子が B(dan) 基側に付加した,B(dan) と B(pin) 基を一つづつ持つジボリルオクテンが,位置および立体選択的に得られることがわかった。なお,この反応の実現には,基質の量比,銅触媒,銅触媒の配位子,塩基,プロトン供給源,溶媒,反応温度,といった、各要因の検討が必要であり,これらを検討した結果,現段階での生成物の収率は 72% である。なお,例えば,塩基としては,KO(t-Bu), NaO(t-Bu), LiOEt, NaOEt, NaOMe, KOH, NaOH、K2CO3, KF, CsF を検討した(Bu: ブチル基,Et: エチル基,Me: メチル基)。溶媒としては,テトファヒドロフラン,1,4-ジオキサン,ジブチルエーテル,ジクロロメタン,クロロベンゼン,を検討した。

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  • アルキニル-B(dan) を多様な有機分子へと導く合成化学的活用に関する研究

    Grant number:19K05484  2019.4 - 2023.3

    日本学術振興会  科学研究費助成事業  基盤研究(C)

    土本 晃久

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

    本申請課題の当初の目的は,当研究室で様々な誘導体の合成に成功したアルキニル-B(dan) 1 を,多様な遷移金属触媒反応の基質として利用できることを明らかにし,これをもとに,有用有機分子の合成に繋げることであった。大別しては,[1] 1 の C(sp)-B(dan) 結合の遷移金属触媒直接変換と,[2] 1 の C≡C結合へのジボリル化と,生じるトリボリルアルケンに対する,位置選択的な繰返しの炭素-炭素結合伸長反応によるπ共役拡張分子の自在合成,の二つの実現を
    目指した。
    [1] に関して:前年度において,銅触媒によって炭素-B(Me2dan) 結合が直接反応に利用できることを明らかにし,アルキニルーB(Me2dan) と 2-オキサゾリジノンを反応さるイナミド合成反応において,生成物がおおよそ 50% の収率で得られる反応条件を見つけていたが,残念ながらこの条件にまさる反応条件の確立には至っていない。収率 80% 以上を目指し,よりよい反応条件の探索を続けているところである。
    [2] に関して:既に B(pin) 基二つと B(dan) 基一つを持つ,多様なトリボリルアルケンの合成を開発・実現し,これを引き続いての位置選択的な鈴木ー宮浦クロスカップリング反応に利用できることを見つけ,研究成果を報告しているが,今回は,全て異なるボリル基からなるトリボリルアルケンが合成できることを見つけた。現状では,このトリボロルアルケンの,引き続いての鈴木ー宮浦クロスカップリング反応が位置選択的に進行するかどうか,について検討している段階である。

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  • 脱水素反応によるケイ素・ホウ素含有芳香族複素環化合物の効率的な実用的合成法の開発

    2015.4 - 2019.3

    基盤研究(C) 

    土本晃久

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    Authorship:Principal investigator  Grant type:Competitive

    Grant amount:\4940000 ( Direct Cost: \3800000 、 Indirect Cost:\1140000 )

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  • 脱水素シリル化反応による有用有機ケイ素化合物の効率的な実用的合成法の開発

    2012.4 - 2015.3

    基盤研究 (C) 

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    Grant type:Competitive

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  • β-アルキルピロール類の実用的な革新的1段階合成法の開発

    2009.4 - 2012.3

    若手研究 (B) 

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    Grant type:Competitive

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  • 芳香族求核置換反応を利用するビアリールおよびトリアリール類の革新的合成法の開発

    2007.4 - 2009.3

    若手研究 (B) 

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