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Development of Novel Chiral Dinuclear Complexes for Catalytic Asymmetric C-H Bond Functionalization

Research Project

Project/Area Number 17H03049
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Research Field Synthetic chemistry
Research InstitutionHokkaido University

Principal Investigator

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

Project Period (FY) 2017-04-01 – 2020-03-31
Project Status Completed (Fiscal Year 2020)
Budget Amount *help
¥17,810,000 (Direct Cost: ¥13,700,000、Indirect Cost: ¥4,110,000)
Fiscal Year 2019: ¥5,850,000 (Direct Cost: ¥4,500,000、Indirect Cost: ¥1,350,000)
Fiscal Year 2018: ¥5,850,000 (Direct Cost: ¥4,500,000、Indirect Cost: ¥1,350,000)
Fiscal Year 2017: ¥6,110,000 (Direct Cost: ¥4,700,000、Indirect Cost: ¥1,410,000)
Keywords不斉触媒 / 不斉合成 / C-H活性化 / パラジウム / シッフ塩基 / 複核触媒 / 不斉配位子
Outline of Final Research Achievements

In this research, we tried to develop a new catalyst for enantio-induction. The generation of active metal species for C-H activation under unique chiral environment was the key. To achieve original and novel chiral system, dinucleating Schiff base system was designed. After intensive optimization of the catalyst structure and catalysts modules, we found that the chiral dinuclear Schiff base catalyst consisted of chiral binaphthyl diamine, chiral sulfoxide unit, palladium and copper was the best, showing high catalytic activity as well as enantioselctivity in intramolecular allylic C-H amination reactions. Broad substrate scope was also confirmed using the Pd-Cu Schiff base catalyst.

Academic Significance and Societal Importance of the Research Achievements

有機化合物に普遍的に存在する炭素ー水素結合のうち、特定の部分を化学選択的に活性化し、化学変換するプロセスは廃棄物の少ない環境調和性の高い合成手法の開発に繋がる。特に、医薬品に見られる含窒素化合物の立体選択的な合成法は得られる生成物の付加価値が高く、その効率的かつ環境調和性の高い合成法の開発が強く求められている。本研究では、炭素ー水素結合を選択的に活性化し、窒素基を導入する新しいキラル触媒の創出に取り組み、従来法では得られない生成物を得る手法を確立した。

Report

(4 results)
  • 2020 Final Research Report ( PDF )
  • 2019 Annual Research Report
  • 2018 Annual Research Report
  • 2017 Annual Research Report
  • Research Products

    (15 results)

All 2021 2020 2019 2018 2017 Other

All Journal Article (5 results) (of which Peer Reviewed: 4 results) Presentation (9 results) (of which Int'l Joint Research: 3 results,  Invited: 4 results) Remarks (1 results)

  • [Journal Article] Metal-Containing Schiff Base/Sulfoxide Ligands for Pd(II)-Catalyzed Asymmetric Allylic C-H Aminations2021

    • Author(s)
      Bunno Youka、Tsukimawashi Yuta、Kojima Masahiro、Yoshino Tatsuhiko、Matsunaga Shigeki
    • Journal Title

      ACS Catalysis

      Volume: 11 Issue: 5 Pages: 2663-2668

    • DOI

      10.1021/acscatal.0c05261

    • NAID

      120007191784

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] One-Step Synthesis of 4H-3,1-Benzoxazin-4-ones from Weinreb Amides and 1,4,2-Dioxazol-5-ones via Cobalt-Catalyzed C-H Bond Activation2019

    • Author(s)
      Tanimoto Iku、Kawai Kentaro、Sato Akane、Yoshino Tatsuhiko、Matsunaga Shigeki
    • Journal Title

      HETEROCYCLES

      Volume: 99 Issue: 1 Pages: 118-118

    • DOI

      10.3987/com-18-s(f)48

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] 5-((3-Bromoallyl)Sulfonyl)-1H-Tetrazoles for Bromodiene Synthesis2018

    • Author(s)
      Matsunaga Shigeki、Suzuki Takuro、Fukagawa Seiya、Yoshino Tatsuhiko、Anada Masahiro
    • Journal Title

      HETEROCYCLES

      Volume: 97 Issue: 2 Pages: 1304-1304

    • DOI

      10.3987/com-18-s(t)90

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Cobalt-Catalyzed C(sp3)-H Functionalization Reactions2018

    • Author(s)
      Yoshino Tatsuhiko、Matsunaga Shigeki
    • Journal Title

      Asian Journal of Organic Chemistry

      Volume: 7 Issue: 7 Pages: 1193-1205

    • DOI

      10.1002/ajoc.201800195

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Total Synthesis of Brasilicardins A and C2017

    • Author(s)
      Anada Masahiro、Hanari Taiki、Kakita Kosuke、Kurosaki Yasunobu、Katsuse Kazuki、Sunadoi Yuta、Jinushi Yu、Takeda Koji、Matsunaga Shigeki、Hashimoto Shunichi
    • Journal Title

      Organic Letters

      Volume: 19 Issue: 20 Pages: 5581-5584

    • DOI

      10.1021/acs.orglett.7b02728

    • Related Report
      2017 Annual Research Report
  • [Presentation] Catalyst Design for Asymmetric C-H Functionalization2021

    • Author(s)
      Shigeki Matsunaga
    • Organizer
      Dalian University of Technology Overseas Partner Universities Series Online Exchange Conference
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Catalyst Design for Asymmetric C-H Functionalization2021

    • Author(s)
      Shigeki Matsunaga
    • Organizer
      Nanyang Technological University Virtual Seminar
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] 不斉C-H結合官能基化を目指した新規キラル触媒の創製2020

    • Author(s)
      松永茂樹
    • Organizer
      近畿化学協会有機金属化学部会第3回例会
    • Related Report
      2019 Annual Research Report
    • Invited
  • [Presentation] 不斉C-H結合官能基化を目指した新規キラル触媒の創製2020

    • Author(s)
      松永茂樹
    • Organizer
      京都大学オンライン特別講演会
    • Related Report
      2019 Annual Research Report
    • Invited
  • [Presentation] 面不斉フェロセンカルボン酸の合成および不斉C-H活性化反応への適用2019

    • Author(s)
      関根大地, 小島正寛, 吉野達彦, 松永茂樹
    • Organizer
      日本化学会第99回春季年会
    • Related Report
      2018 Annual Research Report
  • [Presentation] Cp*Rh/キラルアニオンハイブリッド触媒による不斉分子内オキシアミノ化反応2019

    • Author(s)
      廣瀨純平、佐竹瞬、小島正寛、波多野学、石原一彰、吉野達彦、松永茂樹
    • Organizer
      日本化学会第99回春季年会
    • Related Report
      2018 Annual Research Report
  • [Presentation] Cp*Co(III)触媒によるWeinreb amideを配向基としたC(sp2)-H官能基化反応2018

    • Author(s)
      河合 賢太郎,田中 亮,文野 優華,吉野 達彦,松永 茂樹
    • Organizer
      日本薬学会北海道支部第145回例会
    • Related Report
      2018 Annual Research Report
  • [Presentation] Catalytic Asymmetric Ring-Opening of meso-Aziridines with 2-Fluoromalonetes under Heterodinuclear Rare Earth Metal Schiff Base Catalysis2018

    • Author(s)
      S. Fukagawa, M. Anada, T. Yoshino, S. Matsunaga
    • Organizer
      1st Sino-Japanese Symposium on Catalysis for Precision Synthesis
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research
  • [Presentation] 有機ゲルマニウム化合物の新規合成法の開発とその応用2018

    • Author(s)
      松岡慶太郎, 駒見成実, 小島正寛, 吉野達彦, 松永茂樹
    • Organizer
      第44回反応と合成の進歩シンポジウム
    • Related Report
      2018 Annual Research Report
  • [Remarks] 北海道大学薬学部薬品製造化学研究室:発表論文

    • URL

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

    • Related Report
      2019 Annual Research Report

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Published: 2017-04-28   Modified: 2022-01-27  

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