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Development of Electrophilic C-H Borylation Using Boron Triiodide

Research Project

Project/Area Number 18K14228
Research Category

Grant-in-Aid for Early-Career Scientists

Allocation TypeMulti-year Fund
Review Section Basic Section 33020:Synthetic organic chemistry-related
Research InstitutionKwansei Gakuin University

Principal Investigator

Oda Susumu  関西学院大学, 理工学部, 助教 (00789901)

Project Period (FY) 2018-04-01 – 2020-03-31
Project Status Completed (Fiscal Year 2019)
Budget Amount *help
¥3,900,000 (Direct Cost: ¥3,000,000、Indirect Cost: ¥900,000)
Fiscal Year 2019: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
Fiscal Year 2018: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
Keywords求電子的C-Hホウ素化反応 / 有機ホウ素化合物 / 三ヨウ化ホウ素 / 求電子的C-Hホウ素化 / ホウ素化反応 / 芳香族化合物
Outline of Final Research Achievements

Electrophilic C-H borylation has attracted considerable attention as a transition metal-free approach for the synthesis of arylboron compounds. However, conventional methods require stoichiometric amounts of additives such as Lewis acids and bases. Therefore, development of additive-free borylation processes with a broad substrate scope is highly desirable. Herein, we report the electrophilic C-H borylation of arenes by employing BI3 in the absence of precious metal catalysts and additives. This simple system is applicable to the preparation of various arylboron compounds and multiple borylation of polycyclic aromatic compounds.

Academic Significance and Societal Importance of the Research Achievements

近年,求電子的C-Hホウ素化反応は,有機ホウ素化合物の簡便な合成法として注目されている。しかしながら,従来の手法では化学量論量の添加剤を用いる必要があるため,産業廃棄物が増えるなどの問題が挙げられる。これに対し,本研究では高活性かつ安価な反応剤である三ヨウ化ホウ素を用いることで,添加剤を必要としない求電子的C-Hホウ素化反応の開発に成功した。これにより,環境への負荷の低減だけでなく,ホウ素化反応における大幅なコスト削減が見込まれる。また,創薬や触媒化学,材料化学,高分子化学といった多様な分野における分子設計に新たな選択肢を与えることが期待される。

Report

(3 results)
  • 2019 Annual Research Report   Final Research Report ( PDF )
  • 2018 Research-status Report
  • Research Products

    (6 results)

All 2020 2019

All Journal Article (4 results) (of which Peer Reviewed: 4 results) Presentation (2 results) (of which Int'l Joint Research: 1 results)

  • [Journal Article] Multiple Electrophilic C-H Borylation of Arenes Using Boron Triiodide2020

    • Author(s)
      Oda Susumu、Ueura Kenta、Kawakami Bungo、Hatakeyama Takuji
    • Journal Title

      Organic Letters

      Volume: 22 Issue: 2 Pages: 700-704

    • DOI

      10.1021/acs.orglett.9b04483

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Multiple Resonance Effect-Induced Sky-Blue Thermally Activated Delayed Fluorescence with a Narrow Emission Band2019

    • Author(s)
      Oda Susumu、Kawakami Bungo、Kawasumi Ryosuke、Okita Ryota、Hatakeyama Takuji
    • Journal Title

      Organic Letters

      Volume: 21 Issue: 23 Pages: 9311-9314

    • DOI

      10.1021/acs.orglett.9b03342

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of Tetracoordinate Boron‐Fused Benzoaceanthrylene Analogs via Tandem Electrophilic C-H Borylation2019

    • Author(s)
      Oda Susumu、Abe Hiroaki、Yasuda Nobuhiro、Hatakeyama Takuji
    • Journal Title

      Chemistry - An Asian Journal

      Volume: 印刷中 Issue: 10 Pages: 1657-1661

    • DOI

      10.1002/asia.201801682

    • Related Report
      2018 Research-status Report
    • Peer Reviewed
  • [Journal Article] Tetracoordinate Boron-Fused Double [5]Helicenes as Cathode Active Materials for Lithium Batteries2019

    • Author(s)
      Oda Susumu、Shimizu Takeshi、Katayama Takazumi、Yoshikawa Hirofumi、Hatakeyama Takuji
    • Journal Title

      Organic Letters

      Volume: 21 Issue: 6 Pages: 1770-1773

    • DOI

      10.1021/acs.orglett.9b00337

    • Related Report
      2018 Research-status Report
    • Peer Reviewed
  • [Presentation] Synthesis and Physical Properties of Tetracoordinate Boron-Fused Double Helicenes2019

    • Author(s)
      Susumu Oda, Takeshi Shimizu, Takazumi Katayama, Hirofumi Yoshikawa, and Takuji Hatakeyama
    • Organizer
      The 18th International Symposium on Novel Aromatic Compounds
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research
  • [Presentation] 4配位ホウ素を縮環部に有するダブルヘリセンの合成と物性2019

    • Author(s)
      小田 晋,清水 剛志,片山 敬純,吉川 浩史,畠山 琢次
    • Organizer
      日本化学会第99春季年会
    • Related Report
      2018 Research-status Report

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Published: 2018-04-23   Modified: 2021-02-19  

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