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Dearomatizing Conversion of Aromatic Compounds Based on Addition Reactions of Boron Reagents

Research Project

Project/Area Number 25620082
Research Category

Grant-in-Aid for Challenging Exploratory Research

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

Principal Investigator

Ohmura Toshimichi  京都大学, 工学(系)研究科(研究院), 准教授 (00378803)

Project Period (FY) 2013-04-01 – 2016-03-31
Project Status Completed (Fiscal Year 2015)
Budget Amount *help
¥4,160,000 (Direct Cost: ¥3,200,000、Indirect Cost: ¥960,000)
Fiscal Year 2015: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Fiscal Year 2014: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Fiscal Year 2013: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Keywords合成化学 / 芳香族化合物 / 複素環状化合物 / ホウ素 / 付加反応
Outline of Final Research Achievements

Addition of a diboron reagent into aromatic compounds containing two nitrogen atoms, that is 4,4’-bipyridines, took place efficiently at 60-110 °C under transition-metal-free conditions to give dearomatized compounds in good yields. The boryl group on the dearomatized compounds might be transferred to unsaturated organic molecules, such as pyrazines and alkynes, under mild conditions (room temperature ~ 60 °C). Based on these two elementary reactions, 4,4’-bipyridine-catalyzed diboration of pyrazines and alkynes was established. The insights obtained by this research would be useful for development of molecular transformations based on dearomatization.

Report

(4 results)
  • 2015 Annual Research Report   Final Research Report ( PDF )
  • 2014 Research-status Report
  • 2013 Research-status Report
  • Research Products

    (17 results)

All 2015 2014 2013 Other

All Journal Article (2 results) (of which Peer Reviewed: 2 results,  Acknowledgement Compliant: 1 results) Presentation (13 results) (of which Invited: 6 results) Remarks (2 results)

  • [Journal Article] Organocatalytic Diboration Involving “Reductive Addition” of a Boron-Boron σ-Bond to 4,4’-Bipyridine2015

    • Author(s)
      Toshimichi Ohmura, Yohei Morimasa, Michinori Suginome
    • Journal Title

      J. Am. Chem. Soc.

      Volume: 137 Issue: 8 Pages: 2852-2855

    • DOI

      10.1021/jacs.5b00546

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] 不飽和有機分子の触媒的ボリル化・シリル化の新展開:遷移金属触媒による精密反応制御と有機合成への応用2013

    • Author(s)
      大村智通
    • Journal Title

      有機合成化学協会誌

      Volume: 71 Pages: 804-817

    • NAID

      10031191017

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Presentation] Novel Molecular Transformations Based on Catalytic Activation of Boron-Containing σ-Bonds by Transition Metals or 4,4'-Bipyridines2015

    • Author(s)
      Toshimichi Ohmura
    • Organizer
      Pacifichem 2015
    • Place of Presentation
      Honolulu, Hawaii, USA
    • Year and Date
      2015-12-18
    • Related Report
      2015 Annual Research Report
    • Invited
  • [Presentation] ホウ素反応剤を用いる触媒的分子変換反応の開拓 -常識を越える新反応を求めて-2015

    • Author(s)
      大村智通
    • Organizer
      触媒学会有機金属研究会  オルガノメタリックセミナー2015 「新しい分子変換に挑戦する有機金属化学」
    • Place of Presentation
      東北大学
    • Year and Date
      2015-10-30
    • Related Report
      2015 Annual Research Report
    • Invited
  • [Presentation] ホウ素-ホウ素σ結合の”還元的付加”を鍵とする有機分子触媒ジホウ素化反応2015

    • Author(s)
      大村智通、守政陽平、杉野目道紀
    • Organizer
      第62回有機金属化学討論会
    • Place of Presentation
      関西大学
    • Year and Date
      2015-09-08
    • Related Report
      2015 Annual Research Report
  • [Presentation] 4,4'-Bipyridine-Catalyzed Diboration through "Reductive Addition" of Boron-Boron σ-Bond2015

    • Author(s)
      Toshimichi Ohmura, Yohei Morimasa, Michinori Suginome
    • Organizer
      18th IUPAC International Symposium on Organometallic Chemistry Directed Towards Organic Synthesis (OMCOS 18)
    • Place of Presentation
      Barcelona, Spain
    • Year and Date
      2015-07-29
    • Related Report
      2015 Annual Research Report
  • [Presentation] Novel Molecular Transformations Using Boron Reagents and Catalysts2015

    • Author(s)
      Toshimichi Ohmura
    • Organizer
      Chuo Organometallic Seminar
    • Place of Presentation
      Chuo University, Tokyo
    • Year and Date
      2015-06-27
    • Related Report
      2015 Annual Research Report
    • Invited
  • [Presentation] 4,4'-Bipyridine-Catalyzed Boron-Boron Bond Activation for Diboration of Alkynes2015

    • Author(s)
      Toshimichi Ohmura, Yohei Morimasa, Michinori Suginome
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      日本大学
    • Year and Date
      2015-03-28
    • Related Report
      2014 Research-status Report
  • [Presentation] ホウ素反応剤を用いる触媒的分子変換の新展開2015

    • Author(s)
      大村智通
    • Organizer
      近畿化学協会ヘテロ原子部会平成26年度第3回懇話会
    • Place of Presentation
      大阪科学技術センター
    • Year and Date
      2015-02-12
    • Related Report
      2014 Research-status Report
    • Invited
  • [Presentation] ビピリジンによるホウ素-ホウ素結合切断を触媒的に利用した多置換ピラジンのホウ素化脱芳香化2014

    • Author(s)
      大村智通、守政陽平、杉野目道紀
    • Organizer
      第4回CSJ化学フェスタ
    • Place of Presentation
      タワーホール船堀(東京都)
    • Year and Date
      2014-10-16
    • Related Report
      2014 Research-status Report
  • [Presentation] Transition-Metal-Free Diboration of 4,4'-Bipyridines and Pyrazines: Dearomatization of Nitrogen-Containing Aromatic Compouds on the Basis of B-N Bond Formation2014

    • Author(s)
      Toshimichi Ohmura, Yohei Morimasa, Michinori Suginome
    • Organizer
      IME boron XV
    • Place of Presentation
      Prague, Czech Republic
    • Year and Date
      2014-08-27
    • Related Report
      2014 Research-status Report
  • [Presentation] ホウ素反応剤と遷移金属触媒による新分子変換

    • Author(s)
      大村智通
    • Organizer
      第68回有機化学研究会講演会(白鷺セミナー)
    • Place of Presentation
      大阪府立大学
    • Related Report
      2013 Research-status Report
    • Invited
  • [Presentation] Dearomatizing conversion of pyrazines and bipyridines to their dehydro-derivatives via transition-metal-free addition reaction of boron reagents

    • Author(s)
      Toshimichi Ohmura, Yohei Morimasa, Kazuyuki Oshima, Michinori Suginome
    • Organizer
      14th Tetrahedron Symposium Asia Edition
    • Place of Presentation
      ソウル(韓国)
    • Related Report
      2013 Research-status Report
  • [Presentation] Functionalization of Inert Organic Molecules via Transition-Metal-Catalyzed Reactions with Boron Reagents

    • Author(s)
      Toshimichi Ohmura
    • Organizer
      1st Japanese-American Chemical Society Meeting in Yamaguchi University
    • Place of Presentation
      山口大学
    • Related Report
      2013 Research-status Report
    • Invited
  • [Presentation] ホウ素-窒素結合形成を鍵とする含窒素芳香環の脱芳香化

    • Author(s)
      大村 智通、守政 陽平、杉野目 道紀
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋大学
    • Related Report
      2013 Research-status Report
  • [Remarks] 研究室ホームページ

    • URL

      http://www.sbchem.kyoto-u.ac.jp/suginome-lab/jp/

    • Related Report
      2015 Annual Research Report 2014 Research-status Report
  • [Remarks] 研究室ホームページ

    • URL

      http://www.sbchem.kyoto-u.ac.jp/suginome-lab/jp/

    • Related Report
      2013 Research-status Report

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Published: 2014-07-25   Modified: 2019-07-29  

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