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Development of New Methods for Sequential Remote Bond Formation Based on the Chain Walking Mechanism

Research Project

Project/Area Number 18H01985
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Review Section Basic Section 33020:Synthetic organic chemistry-related
Research InstitutionKeio University

Principal Investigator

Kochi Takuya  慶應義塾大学, 理工学部(矢上), 准教授 (70396779)

Project Period (FY) 2018-04-01 – 2022-03-31
Project Status Completed (Fiscal Year 2022)
Budget Amount *help
¥17,290,000 (Direct Cost: ¥13,300,000、Indirect Cost: ¥3,990,000)
Fiscal Year 2021: ¥3,770,000 (Direct Cost: ¥2,900,000、Indirect Cost: ¥870,000)
Fiscal Year 2020: ¥3,770,000 (Direct Cost: ¥2,900,000、Indirect Cost: ¥870,000)
Fiscal Year 2019: ¥3,770,000 (Direct Cost: ¥2,900,000、Indirect Cost: ¥870,000)
Fiscal Year 2018: ¥5,980,000 (Direct Cost: ¥4,600,000、Indirect Cost: ¥1,380,000)
Keywords遠隔官能基化 / 連続的結合形成 / パラジウム触媒 / ジエン類 / ジボロン / ヒドロボラン / チェーンウォーキング / 環化反応 / ヒドロホウ素化 / ジエン / アルケン / 遠隔位連続結合形成反応 / 連続的結合形成反応
Outline of Final Research Achievements

Various sequential formation of distant bonds was achieved by the use of functionalization reagents such as diborons and hydroboranes in the palladium-catalyzed chain-walking cyclization of 1,n-dienes. Sequential formation of "three" distant bonds, which is unprecedented and difficult to achieve otherwise, was also realized in the reactions of 1,n-dienes (n>6) with diborons. Formal sigma-bond metathesis between Pd-C and B-B bonds,a rarely considered process,is suggested to be involved in the final step of the catalytic cycles of the reaction using diborons and to proceed easily.

Academic Significance and Societal Importance of the Research Achievements

本研究では、離れた位置における連続的結合形成という今までにないタイプの反応をいくつも実現することができた。これらの反応開発は複雑な分子骨格をもつ有機化合物を一挙に作り上げることを可能にするものである。複雑な構造をもつ有機分子の合成には多段階の工程が必要となり、それに伴って多くの化学・エネルギー資源を必要とするが、その効率化・短工程化は環境調和型合成の開発につながる重要な過程である考えられる。

Report

(5 results)
  • 2022 Final Research Report ( PDF )
  • 2021 Annual Research Report
  • 2020 Annual Research Report
  • 2019 Annual Research Report
  • 2018 Annual Research Report
  • Research Products

    (16 results)

All 2023 2022 2021 2019 2018

All Journal Article (7 results) (of which Peer Reviewed: 7 results) Presentation (9 results) (of which Int'l Joint Research: 5 results,  Invited: 2 results)

  • [Journal Article] Desymmetrization of prochiral methylenes by asymmetric chain-walking cyclization using bioxazoline palladium catalysts2023

    • Author(s)
      Shigekane Masayuki、Arai Tomonori、Tamura Makoto、Uchida Tatsuya、Kakiuchi Fumitoshi、Kochi Takuya
    • Journal Title

      Tetrahedron Letters

      Volume: 114 Pages: 154292-154292

    • DOI

      10.1016/j.tetlet.2022.154292

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Palladium-Catalyzed Hydroboration/Cyclization of 1,n-Dienes2023

    • Author(s)
      Kanno Shota、Kakiuchi Fumitoshi、Kochi Takuya
    • Journal Title

      The Journal of Organic Chemistry

      Volume: 88 Issue: 4 Pages: 2621-2630

    • DOI

      10.1021/acs.joc.2c02781

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Remote Arylative Substitution of Alkenes Possessing an Acetoxy Group via β‐Acetoxy Elimination2021

    • Author(s)
      Muto Kazuma、Kumagai Takaaki、Kakiuchi Fumitoshi、Kochi Takuya
    • Journal Title

      Angewandte Chemie International Edition

      Volume: 60 Issue: 46 Pages: 24500-24504

    • DOI

      10.1002/anie.202111396

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Palladium-Catalyzed Remote Diborylative Cyclization of Dienes with Diborons via Chain Walking2021

    • Author(s)
      Kanno Shota、Kakiuchi Fumitoshi、Kochi Takuya
    • Journal Title

      Journal of the American Chemical Society

      Volume: 143 Issue: 46 Pages: 19275-19281

    • DOI

      10.1021/jacs.1c09705

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Nondissociative chain walking as a strategy in catalytic organic synthesis2019

    • Author(s)
      Kochi Takuya、Kanno Shota、Kakiuchi Fumitoshi
    • Journal Title

      Tetrahedron Letters

      Volume: 60 Issue: 37 Pages: 150938-150938

    • DOI

      10.1016/j.tetlet.2019.07.029

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Metal-Catalyzed Sequential Formation of Distant Bonds in Organic Molecules: Palladium-Catalyzed Hydrosilylation/Cyclization of 1,n-Dienes by Chain Walking2019

    • Author(s)
      Kochi Takuya、Ichinose Kazuya、Shigekane Masayuki、Hamasaki Taro、Kakiuchi Fumitoshi
    • Journal Title

      Angewandte Chemie International Edition

      Volume: 58 Issue: 16 Pages: 5261-5265

    • DOI

      10.1002/anie.201814558

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Selective Long-Distance Isomerization of Terminal Alkenes via Nondissociative Chain Walking2018

    • Author(s)
      Yamasaki Yuya、Kumagai Takaaki、Kanno Shota、Kakiuchi Fumitoshi、Kochi Takuya
    • Journal Title

      The Journal of Organic Chemistry

      Volume: 83 Issue: 16 Pages: 9322-9333

    • DOI

      10.1021/acs.joc.8b01288

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Presentation] パラジウム触媒による脱離基を有する様々な末端アルケンの遠隔位置換型アリール化反応2022

    • Author(s)
      武藤一馬、垣内史敏、河内卓彌
    • Organizer
      日本化学会第102春季年会
    • Related Report
      2021 Annual Research Report
  • [Presentation] パラジウム触媒を用いたジボロンによる様々な1,n-ジエンの遠隔ジボリル化・環化反応2022

    • Author(s)
      菅野翔太、垣内史敏、河内卓彌
    • Organizer
      日本化学会第102春季年会
    • Related Report
      2021 Annual Research Report
  • [Presentation] Nondissociative Chain Walking of Palladium Catalysts: Applications in Organic Reactions and Mechanistic Analyses2022

    • Author(s)
      Takuya Kochi
    • Organizer
      The 11th Singapore International Chemistry Conference (SICC-11)
    • Related Report
      2021 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] ピリジン-イソキサゾールパラジウム触媒による脱離基をもつ末端アルケンの遠隔位置換型アリール化反応2021

    • Author(s)
      武藤一馬、垣内史敏、河内卓彌
    • Organizer
      第67回有機金属化学討論会
    • Related Report
      2021 Annual Research Report
  • [Presentation] パラジウム触媒を用いたチェーンウォーキングを経るジエンの遠隔ジボリル化・環化反応2021

    • Author(s)
      菅野翔太、垣内史敏、河内卓彌
    • Organizer
      第67回有機金属化学討論会
    • Related Report
      2021 Annual Research Report
  • [Presentation] Palladium-Catalyzed Remote Arylative Substitution of Alkenes Bearing a Distant Acetoxy Group2021

    • Author(s)
      Kazuma Muto, Takaaki Kumagai, Fumitoshi Kakiuchi, and Takuya Kochi
    • Organizer
      The 2021 International Chemical Congress of Pacific Basin Societies (Pacifichem 2021)
    • Related Report
      2021 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Palladium-Catalyzed Remote Diborylative Cyclization of Dienes via Chain Walking2021

    • Author(s)
      Shota Kanno, Fumitoshi Kakiuchi, and Takuya Kochi
    • Organizer
      The 2021 International Chemical Congress of Pacific Basin Societies (Pacifichem 2021)
    • Related Report
      2021 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Development of Effective Strategies for Closure of Catalytic Cycles of Reactions via Palladium-Catalyzed Nondissociative Chain Walking2019

    • Author(s)
      Takuya Kochi
    • Organizer
      The 20th IUPAC International Symposium on Organometallic Catalysis Directed Towards Organic Synthesis
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Nondissociative Chain Walking as an Innovative Strategy for Functionalization of Organic Molecules2018

    • Author(s)
      Takuya Kochi
    • Organizer
      The 4th International Conference on Organometallic and Catalysis 2018 (OM&Cat 2018)
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research / Invited

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Published: 2018-04-23   Modified: 2024-01-30  

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