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Development of Highly Efficient Methods for Introduction of Boryl Groups for Synthesis of Boron-cotaining Functional p-Electoron Materials

Research Project

Project/Area Number 16K13987
Research Category

Grant-in-Aid for Challenging Exploratory Research

Allocation TypeMulti-year Fund
Research Field Synthetic chemistry
Research InstitutionHokkaido University

Principal Investigator

Ishiyama Tatsuo  北海道大学, 工学研究院, 准教授 (00232348)

Co-Investigator(Kenkyū-buntansha) 関 朋宏  北海道大学, 工学研究院, 助教 (50638187)
Research Collaborator Shishido Ryosuke  
Project Period (FY) 2016-04-01 – 2019-03-31
Project Status Completed (Fiscal Year 2018)
Budget Amount *help
¥3,770,000 (Direct Cost: ¥2,900,000、Indirect Cost: ¥870,000)
Fiscal Year 2018: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2017: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000)
Fiscal Year 2016: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000)
Keywords有機エレクトロニクス / 芳香族C-Hホウ素化反応 / ジアリールボロン誘導体 / 機能性有機材料 / 炭素ー水素結合の活性化 / ジメシチルボリル化 / ベンゾフラン / 合成化学 / 有機材料化学 / ホウ素化反応 / 炭素ー水素結合活性化 / ファインケミカルズ
Outline of Final Research Achievements

Utilization boron, a group 13 element, as a key element for developing new functional electronic and optoelectronic materials is an important direction in the organoboron chemistry. Boron has several characteristic features, such as trigonal planar geometry for trivalent boron compounds, high Lewis acidity, and effective orbital interaction with pai-conjugated frameworks through the vacant p-orbital. To introduce boryl groups into pai-conjugated systems, one of the most simple and efficient methods is aromatic C-H boryation. We found that aromatic C-H borylation of Furan and its dervatives by dimesitylborylsilane derivatives proceeded smoothly in the presence of catalytic amount of (IMes)Ir(cod)Cl and AgOAc to provide the corresponding dimesytylborylfuran and its derivatives in high yields.

Academic Significance and Societal Importance of the Research Achievements

ホウ素を介して連結したπ共役系分子は、高いπ電子受容性をもち、特異な発光特性を示すため、電子輸送材料や有機EL材料への応用が期待される重要なホウ素化合物である。本研究では、官能基許容性、経済性、環境、および原子効率にも配慮した力量ある共役有機化合物へのジアリールホウ素基の導入法として、遷移金属触媒を用いたsp2炭素―水素結合のテトラアリールジボロン、ジアリールボロンあるいはシリルジアリールボロンによる直接的なホウ素化反応の開発を行った。

Report

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

    (9 results)

All 2018 2017 2016

All Journal Article (2 results) (of which Int'l Joint Research: 2 results,  Peer Reviewed: 2 results,  Open Access: 2 results,  Acknowledgement Compliant: 1 results) Presentation (7 results) (of which Int'l Joint Research: 2 results)

  • [Journal Article] Regioselective C-H Borylation of Heteroaromatic Aldimines with Iridium Complexes2016

    • Author(s)
      Sasaki, I.; Ikeda, T.; Amou, T.; Taguchi, J.; Ito, H.; Ishiyama, T.
    • Journal Title

      Synlett

      Volume: 27 Issue: 10 Pages: 1582-1586

    • DOI

      10.1055/s-0035-1561578

    • NAID

      120005981400

    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Open Access / Int'l Joint Research / Acknowledgement Compliant
  • [Journal Article] Iridium(I)-catalyzed C-H Borylation of α,β-Unsaturated Esters with Bis(pinacolato)diboron2016

    • Author(s)
      Sasaki, I.; Taguchi, J.; Doi, H.; Ito, H.; Ishiyama, T.
    • Journal Title

      Chem. Asian J.

      Volume: 11 Issue: 9 Pages: 1400-1405

    • DOI

      10.1002/asia.201600078

    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Presentation] Iridium-Catalyzed C-H Dimesitylborylation of Benzofurans with Silyldimesitylborane2018

    • Author(s)
      SHISHIDO, Ryosuke; SASAKI, Ikuo; SEKI, Tomohiro; ISHIYAMA, Tatsuo; ITO, Hajime
    • Organizer
      日本化学会第98春季年会
    • Related Report
      2018 Annual Research Report 2017 Research-status Report
  • [Presentation] Direct Introduction of Dimesitylboryl Group into Benzofurans via Iridium-Catalyzed C-H Activation2018

    • Author(s)
      Ryosuke Shishido, Ikuo Sasaki, Tomohiro Seki, Tatsuo Ishiyama, Hajime Ito
    • Organizer
      16th Boron Chemistry Meeting in the Americas
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research
  • [Presentation] イリジウム触媒による芳香族C-H結合活性化を用いたベンゾフランへのジメシチルボリル基導入反応の開発2018

    • Author(s)
      宍戸 亮介
    • Organizer
      第51回有機金属若手の会
    • Related Report
      2018 Annual Research Report
  • [Presentation] Iridiumu-Catalyzed C-H Dimesitylborylation of Benzofurans2018

    • Author(s)
      宍戸 亮介
    • Organizer
      第4回野依フォーラム若手育成塾
    • Related Report
      2018 Annual Research Report
  • [Presentation] Development of Direct Introduction Method of Dimesitylboryl Group via Iridium-Catalyzed Aromatic C-H Activation2018

    • Author(s)
      Ryosuke Shishido, Ikuo Sasaki, Tomohiro Seki, Tatsuo Ishiyama, Hajime Ito
    • Organizer
      The Fourth International Symposium on C-H Activation
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research
  • [Presentation] イリジウム触媒によるベンゾフラン類のC-Hジメシチルボリル化反応の開発2017

    • Author(s)
      宍戸 亮介・佐々木 郁雄・関 朋宏・石山 竜生・伊藤 肇
    • Organizer
      第50回有機金属若手の会夏の学校
    • Related Report
      2017 Research-status Report
  • [Presentation] イリジウム触媒を用いたα,β-不飽和カルボニル化合物のビニルC-H結合ホウ素化反応2016

    • Author(s)
      田口純平
    • Organizer
      第49回有機金属若手の会
    • Place of Presentation
      東海大学嬬恋高原研修センター(群馬県吾妻郡嬬恋村)
    • Year and Date
      2016-07-11
    • Related Report
      2016 Research-status Report

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Published: 2016-04-21   Modified: 2020-03-30  

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