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Asymmetric C-H Bond Functionalization with Heterodinuclear Asymmetric Catalysts

Research Project

Project/Area Number 26288043
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypePartial Multi-year Fund
Section一般
Research Field Synthetic chemistry
Research InstitutionHokkaido University (2015-2017)
The University of Tokyo (2014)

Principal Investigator

MATSUNAGA Shigeki  北海道大学, 薬学研究院, 教授 (50334339)

Research Collaborator KATO Shota  
KOJIMA Masahiro  
TANAKA Ryo  
IKEMOTO Hideya  
SATAKE Shun  
BUNNO Youka  
SUN Bo  
SUZUKI Yudai  
Project Period (FY) 2014-04-01 – 2018-03-31
Project Status Completed (Fiscal Year 2017)
Budget Amount *help
¥16,510,000 (Direct Cost: ¥12,700,000、Indirect Cost: ¥3,810,000)
Fiscal Year 2016: ¥4,940,000 (Direct Cost: ¥3,800,000、Indirect Cost: ¥1,140,000)
Fiscal Year 2015: ¥4,940,000 (Direct Cost: ¥3,800,000、Indirect Cost: ¥1,140,000)
Fiscal Year 2014: ¥6,630,000 (Direct Cost: ¥5,100,000、Indirect Cost: ¥1,530,000)
KeywordsC-H活性化 / 触媒 / 不斉触媒 / 脱水素 / 立体制御 / 複素環 / 有機金属 / 生物活性化合物
Outline of Final Research Achievements

We have succeeded in stereocontrol in catalytic carbon-hydrogen bond activation reactions by using newly developed catalysts. We also investigated new catalysts that enable control of radical reactive species. Although asymmetric variants have not yet been succeeded, we realized acceptor-less dehydrogenation of tetrahydronaphthalenes and indolines under visible light irradiation at ambient temperature. Finally, we also developed a new chiral heterodinuclear Schiff base catalyst for asymmetric allylic C-H bond functionalization. There still remain rooms for improvement in the enantioselectivity with the heterodinuclear catalyst, but the preliminary results in this study clearly indicated the utility of the present strategy.

Report

(5 results)
  • 2017 Annual Research Report   Final Research Report ( PDF )
  • 2016 Annual Research Report
  • 2015 Annual Research Report
  • 2014 Annual Research Report
  • Research Products

    (8 results)

All 2017 2016 2015 2014 Other

All Journal Article (1 results) (of which Peer Reviewed: 1 results) Presentation (6 results) (of which Invited: 2 results) Remarks (1 results)

  • [Journal Article] Hybrid Catalysis Enabling Room-Temperature Hydrogen Gas Release from N-Heterocycles and Tetrahydronaphthalenes2017

    • Author(s)
      Shota Kato, Yutaka Saga, Masahiro Kojima, Hiromu Fuse, Shigeki Matsunaga, Arisa Fukatsu, Mio Kondo, Shigeyuki Masaoka, and Motomu Kanai
    • Journal Title

      J. Am. Chem. Soc.

      Volume: 139 Issue: 6 Pages: 2204-2207

    • DOI

      10.1021/jacs.7b00253

    • Related Report
      2017 Annual Research Report 2016 Annual Research Report
    • Peer Reviewed
  • [Presentation] キラル対アニオンを導入したCp*Rh(III)錯体によるC-H活性化を経た触媒的不斉1,4-付加反応2017

    • Author(s)
      佐竹瞬、栗原拓丸、西川圭祐、望月拓哉、波多野学、石原一彰、吉野達彦、松永茂樹
    • Organizer
      CSJフェスタ
    • Related Report
      2017 Annual Research Report
  • [Presentation] キラル対アニオンを導入したCp*Rh(III)錯体によるC-H活性化を経た触媒的不斉1,4-付加反応2017

    • Author(s)
      佐竹瞬、栗原拓丸、西川圭祐、望月拓哉、波多野学、石原一彰、吉野達彦、松永茂樹
    • Organizer
      第43回反応と合成の進歩シンポジウム
    • Related Report
      2017 Annual Research Report
  • [Presentation] Cp*Co触媒を用いたピロールのC-Hアルケニル化反応2016

    • Author(s)
      田中亮、池本英也、吉野達彦、金井求、松永茂樹
    • Organizer
      第6回CSJフェスタ2016
    • Place of Presentation
      タワーホール船堀(東京都・江戸川区)
    • Year and Date
      2016-11-14
    • Related Report
      2016 Annual Research Report
  • [Presentation] Rh(II)アミダート錯体を用いたRawalジエンとキラルなアルデヒドとのジアステレオ選択的ヘテロDiels-Alder反応2015

    • Author(s)
      佐竹瞬、鈴木拓郎、棚田文也、渡邊雄大、穴田仁洋、松永茂樹、橋本俊一
    • Organizer
      第5回CSJ化学フェスタ2015
    • Place of Presentation
      タワーホール船堀(東京都江戸川区)
    • Year and Date
      2015-10-13
    • Related Report
      2015 Annual Research Report
  • [Presentation] C-C Bond-Forming Reactions under Proton-Transfer Process -from Asymmetric Catalysis to C-H Functionalization-2015

    • Author(s)
      松永茂樹
    • Organizer
      MBLA10周年記念シンポジウム
    • Place of Presentation
      日大船橋キャンパス
    • Year and Date
      2015-03-29
    • Related Report
      2014 Annual Research Report
    • Invited
  • [Presentation] 第一遷移金属触媒を活用した精密有機合成~不斉合成およびC-H結合直截変換反応~2014

    • Author(s)
      松永茂樹
    • Organizer
      三井化学講演会
    • Place of Presentation
      三井化学袖ヶ浦研究所
    • Year and Date
      2014-11-06
    • Related Report
      2014 Annual Research Report
    • Invited
  • [Remarks]

    • URL

      http://www.pharm.hokudai.ac.jp/yakuzou/publication.html

    • Related Report
      2017 Annual Research Report

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Published: 2014-04-04   Modified: 2019-03-29  

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