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Development of Efficient and Practical Synthetic Method of Silicon- and Boron-Containing Heteroaromatic Compounds by Dehydrogenative Coupling Reaction

Research Project

Project/Area Number 15K05505
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Synthetic chemistry
Research InstitutionMeiji University

Principal Investigator

Tsuchimoto Teruhisa  明治大学, 理工学部, 専任教授 (80313716)

Research Collaborator Matsui Fumiya  
Iketani Yoshihiko  
Sekine Masaru  
Kamakura Daiki  
Sawatsugawa Yuuki  
Utsugi Hirokazu  
Sugiura Tetsuya  
Horio Shin  
Tanabe Mikio  
Tani Tomohiro  
Sano Yusuke  
Hirataka Yo  
Takahashi Naomi  
Hashimoto Sadahiro  
Yonekura Kyohei  
Project Period (FY) 2015-04-01 – 2019-03-31
Project Status Completed (Fiscal Year 2018)
Budget Amount *help
¥4,940,000 (Direct Cost: ¥3,800,000、Indirect Cost: ¥1,140,000)
Fiscal Year 2017: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2016: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Fiscal Year 2015: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Keywords脱水素カップリング / ケイ素 / ホウ素 / 亜鉛 / アルキン / インドール / ピロール / アニリン / ルイス酸 / 複素環 / 反応機構
Outline of Final Research Achievements

During the research period of four years, I developed the following three types of dehydrogenative coupling reactions including synthetic applications of products: (1) zinc Lewis acid-catalyzed dehydrogenative silylation of indoles, pyrroles, and anilines; (2) zinc Lewis acid-catalyzed dehydrogenative borylation of alkynes for synthesizing alkynyl-B(dan)s and their synthetic applications; (3) zinc-indium Lewis acid-catalyzed one-step synthesis of gem-disilylalkenes by sequential reaction of dehydrogenative coupling followed by cyclization.

Academic Significance and Societal Importance of the Research Achievements

本研究では,インドール,ピロール,アニリン,アルキンといった,様々な有機化合物を,ケイ素化合物の H-Si 結合やホウ素化合物の H-B 結合と,脱水素カップリングさせる際に,世界で初めて,ルイス酸触媒を利用することに成功した。これまで,この種の反応には,高価で希少な後周期遷移金属からなる錯体が触媒に使われてきたが,研究代表者が実現した反応は,豊富な金属資源としての,安価な,亜鉛からなる金属塩を触媒に使うものであり,従来の反応とは一線を画すものである。この実現は,持続可能な科学技術の実現を目指す本国にとって,極めて意義深いものであり,本研究の実現による学術的意義や社会的意義は大きい。

Report

(5 results)
  • 2018 Annual Research Report   Final Research Report ( PDF )
  • 2017 Research-status Report
  • 2016 Research-status Report
  • 2015 Research-status Report
  • Research Products

    (11 results)

All 2019 2018 2017 2016 2015 Other

All Journal Article (2 results) (of which Peer Reviewed: 2 results) Presentation (6 results) (of which Int'l Joint Research: 1 results) Remarks (2 results) Patent(Industrial Property Rights) (1 results)

  • [Journal Article] Alkynyl-B(dan)s in Various Palladium‐Catalyzed Carbon-Carbon Bond‐Forming Reactions Leading to Internal Alkynes, 1,4‐Enynes, Ynones, and Multiply Substituted Alkenes2019

    • Author(s)
      Tani Tomohiro、Sawatsugawa Yuuki、Sano Yusuke、Hirataka Yo、Takahashi Naomi、Hashimoto Sadahiro、Sugiura Tetsuya、Tsuchimoto Teruhisa
    • Journal Title

      Advanced Synthesis & Catalysis

      Volume: 361 Issue: 8 Pages: 1815-1834

    • DOI

      10.1002/adsc.201801527

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Zinc-Catalyzed Dehydrogenative Silylation of Indoles2017

    • Author(s)
      Kyohei Yonekura , Yoshihiko Iketani, Masaru Sekine, Tomohiro Tani, Fumiya Matsui, Daiki Kamakura, and Teruhisa Tsuchimoto*
    • Journal Title

      Organometallics

      Volume: 36 Issue: 17 Pages: 3234-3249

    • DOI

      10.1021/acs.organomet.7b00382

    • Related Report
      2017 Research-status Report
    • Peer Reviewed
  • [Presentation] 医薬品や電子材料を指向した,アルキニル-B(dan) の四置換アルケン合成への利用2018

    • Author(s)
      髙橋尚美・澤津川友輝・谷 智弘・土本晃久
    • Organizer
      第 8 回 CSJ 化学フェスタ
    • Related Report
      2018 Annual Research Report
  • [Presentation] Synthetic Utilization of a C(sp)-B(dan) bond under Palladium Catalysis2018

    • Author(s)
      Tomohiro Tani, Tetsuya Sugiura, Naomi Takahashi, Sadahiro Hashimoto, Teruhisa Tsuchimoto
    • Organizer
      The 14th International Kyoto Conference on New Aspects of Organic Chemistry (IKCOC-14)
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Zinc-Catalyzed Dehydrogenative Stannylation of Terminal Alkynes with Hydrostannanes2017

    • Author(s)
      甲斐雄一・屋伸哉・土本晃久
    • Organizer
      有機金属化学討論会
    • Related Report
      2017 Research-status Report
  • [Presentation] 亜鉛-ピリジン触媒システムによる末端アルキンの脱水素ボリル化反応2016

    • Author(s)
      平高遥・谷智弘・卯都木裕一・杉浦哲也・堀尾慎・佐野悠介・土本晃久
    • Organizer
      第 6 回 CSJ 化学フェスタ 2016
    • Place of Presentation
      タワーホール船堀・東京
    • Year and Date
      2016-11-14
    • Related Report
      2016 Research-status Report
  • [Presentation] Zinc-Catalyzed Dehydrogenative Borylation of Terminal Alkynes2016

    • Author(s)
      谷智弘・卯都木裕一・杉浦哲也・堀尾慎・佐野悠介・土本晃久
    • Organizer
      有機金属化学討論会
    • Place of Presentation
      早稲田大学・東京
    • Year and Date
      2016-09-14
    • Related Report
      2016 Research-status Report
  • [Presentation] 亜鉛触媒によるヒドロシランを用いたインドール類の脱水素シリル化反応2015

    • Author(s)
      松井史也・池谷 慶彦・関根 大・鎌倉 大貴・土本 晃久
    • Organizer
      第 32 回有機合成化学セミナー
    • Place of Presentation
      湯河原・静岡 (ニューウェルシティ湯河原)
    • Year and Date
      2015-09-15
    • Related Report
      2015 Research-status Report
  • [Remarks] 土本研究室ホームページ

    • URL

      http://www.isc.meiji.ac.jp/~tsuchi/

    • Related Report
      2018 Annual Research Report 2017 Research-status Report 2015 Research-status Report
  • [Remarks] 土本研究室ホームページ

    • URL

      http://www.isc.meiji.ac.jp/~tsuchi/index.html

    • Related Report
      2016 Research-status Report
  • [Patent(Industrial Property Rights)] 新規なトリボリルアルケン,その製造方法,及び多置換アルケンの製造方法2018

    • Inventor(s)
      土本晃久
    • Industrial Property Rights Holder
      土本晃久
    • Industrial Property Rights Type
      特許
    • Industrial Property Number
      2018-126542
    • Filing Date
      2018
    • Related Report
      2018 Annual Research Report

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Published: 2015-04-16   Modified: 2021-12-27  

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