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Development of Catalytic Processes I nvo I v i ng Multiple Elements Based on Formation of Metalloid裕ransition Metal Intermediates and Control of Their Reactions

Research Project

Project/Area Number 22685010
Research Category

Grant-in-Aid for Young Scientists (A)

Allocation TypeSingle-year Grants
Research Field Synthetic chemistry
Research InstitutionKyoto University

Principal Investigator

OHMURA Toshimichi  京都大学, 工学研究科, 准教授 (00378803)

Project Period (FY) 2010 – 2012
Project Status Completed (Fiscal Year 2012)
Budget Amount *help
¥25,350,000 (Direct Cost: ¥19,500,000、Indirect Cost: ¥5,850,000)
Fiscal Year 2012: ¥4,420,000 (Direct Cost: ¥3,400,000、Indirect Cost: ¥1,020,000)
Fiscal Year 2011: ¥4,420,000 (Direct Cost: ¥3,400,000、Indirect Cost: ¥1,020,000)
Fiscal Year 2010: ¥16,510,000 (Direct Cost: ¥12,700,000、Indirect Cost: ¥3,810,000)
Keywords遷移金属触媒 / メタロイド元素 / 結合形成 / 反応活性種 / 合成化学 / シリレン / 有機ケイ素化合物 / 有機ホウ素化合物
Research Abstract

Transition-metal-catalyzed bond-forming reactions of unsaturated organic substrates with silylene, divalent silicon species, was established, in which silylboronic esters were used as thermally stable and storable silylene precursors. We also found that addition reactions of boron reagents took place efficiently into nitrogen-containing aromatic compounds in the presence of a transition metal catalyst to give dearomatized products. It was suggested that a key accelerating factor in these catalytic processes was boron-nitrogen bond formation.

Report

(4 results)
  • 2012 Annual Research Report   Final Research Report ( PDF )
  • 2011 Annual Research Report
  • 2010 Annual Research Report
  • Research Products

    (35 results)

All 2012 2011 2010 Other

All Journal Article (7 results) (of which Peer Reviewed: 7 results) Presentation (20 results) (of which Invited: 2 results) Book (4 results) Remarks (4 results)

  • [Journal Article] Catalytic Functionalization of Methyl Group on Silicon: Iridium-Catalyzed C(sp3)-H Borylation of Methylchlorosilanes2012

    • Author(s)
      Toshimichi Ohmura, Takeru Torigoe, Michinori Suginome
    • Journal Title

      J. Am. Chem. Soc.

      Volume: 134 Issue: 42 Pages: 17416-17419

    • DOI

      10.1021/ja307956w

    • Related Report
      2012 Annual Research Report 2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] Dearomatizing Conversion of Pyrazines to 1,4-Dihydropyrazine Derivatives via Transition-Metal-FreeDiboration2012

    • Author(s)
      Kazuyuki Oshima, Toshimichi Ohmura, Michinori Suginome
    • Journal Title

      Silaboration, and Hydroboration, Chem. Commun.

      Volume: 48 Issue: 68 Pages: 8571-8573

    • DOI

      10.1039/c2cc34086k

    • Related Report
      2012 Annual Research Report 2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] Regioselective Synthesis of 1,2-Dihydropyridines by Rhodium-Catalyzed Hydroboration of Pyridines2012

    • Author(s)
      Kazuyuki Oshima, Toshimichi Ohmura, Michinori Suginome
    • Journal Title

      The Journal of American Chemical Society

      Volume: 134 Issue: 8 Pages: 3699-3702

    • DOI

      10.1021/ja3002953

    • Related Report
      2012 Final Research Report 2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Palladium-Catalyzed Regioselective Silaboration of Pyridines Leading to the Synthesis of Silylated Dihydropyridines2011

    • Author(s)
      Kazuyuki Oshima, Toshimichi Ohmura, Michinori Suginome
    • Journal Title

      J. Am. Chem. Soc

      Volume: 138 Pages: 7324-7327

    • Related Report
      2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] 2-Vinylindoles as the Four-Atom Component in a Catalytic [4+1] Cycloaddition with a Silylene-Palladium Species2011

    • Author(s)
      Kohei Masuda, Toshimichi Ohmura, Michinori Suginome
    • Journal Title

      Organometallics

      Volume: 30 Issue: 6 Pages: 1322-1325

    • DOI

      10.1021/om200135u

    • Related Report
      2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] Palladium-Catalyzed Regioselective Silaboration of Pyridines Leading to the Synthesis of Silylated Dihydropyridines2011

    • Author(s)
      Kazuyuki Oshima, Toshimichi Ohmura, Michinori Suginome
    • Journal Title

      The Journal of American Chemical Society

      Volume: 133 Issue: 19 Pages: 7324-7327

    • DOI

      10.1021/ja2020229

    • Related Report
      2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] 2-Vinylindoles As the Four-Atom Component in a Catalytic [4+1] Cycloaddition with a Silylene-Palladium Species Generated from (Aminosilyl) boronic Ester2011

    • Author(s)
      Kohei Masuda, Toshimichi Ohmura, Michinori Suginome
    • Journal Title

      Organometallics

      Volume: 30 Pages: 1322-1325

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Presentation] Dearomatizing Conversion of Nitrogen-Containing Aromatic Compounds via Addition Reaction of Boron Reagents2012

    • Author(s)
      Toshimichi Ohmura
    • Organizer
      The 2nd International Kyoto Symposium on Organic Nanostructures
    • Place of Presentation
      京都大学桂キャンパス(京都市)
    • Year and Date
      2012-11-08
    • Related Report
      2012 Final Research Report
  • [Presentation] Transition-Metal- Catalyzed Synthetic Reactions Using Amino(boryl)silane as a Silylene Equivalent2012

    • Author(s)
      Toshimichi Ohmura
    • Organizer
      The 4th Asian Silicon Svmnosium
    • Place of Presentation
      つくば国際会議場(つくば市
    • Year and Date
      2012-10-22
    • Related Report
      2012 Final Research Report
  • [Presentation] Rhodium-Catalyzed Regioselective Hydroboration of Pyridines, Giving1 ,2-Dihydropyridines2012

    • Author(s)
      Toshimichi Ohmura, Kazuyuki Oshima, Michinori Suginome
    • Organizer
      XXV International Conference on OrganometallicChemistry
    • Place of Presentation
      リスボン(ポルトガル
    • Year and Date
      2012-09-03
    • Related Report
      2012 Final Research Report
  • [Presentation] ホウ素反応剤を用いる遷移金 属触媒反応の新展開2012

    • Author(s)
      大村智通
    • Organizer
      第45回有機金属 若手の会夏の学校
    • Place of Presentation
      ホ テルェバーグリーン富士(山梨県)
    • Year and Date
      2012-07-10
    • Related Report
      2012 Final Research Report
  • [Presentation] アミノシリル)ボランとパラジウム触媒を用いる炭素一酸素結合へのシリレンの二重挿入によるジシラン生成2012

    • Author(s)
      大村智通、高瀬一郎、杉野目道紀
    • Organizer
      日本化学会第91春季年会
    • Year and Date
      2012-03-11
    • Related Report
      2012 Final Research Report
  • [Presentation] パラ ジウムシリレン種を利用する有機ケイ素 化合物合成:2一ビニルインドールとの触媒 的[4+11環化付加反応2011

    • Author(s)
      大村智通、増田幸平、杉野目道紀
    • Organizer
      第15回ケイ素化 学協会シンポジウム
    • Place of Presentation
      シーパル須磨(兵庫県)
    • Year and Date
      2011-10-22
    • Related Report
      2012 Final Research Report
  • [Presentation] パラジウムシリレン種を利用する有機ケイ素化合物合成:2-ビニルインドールとの触媒的[4+1]環化付加反応2011

    • Author(s)
      大村智通
    • Organizer
      第15回ケイ素化学協会シンポジウム
    • Place of Presentation
      シーパル須磨(兵庫県)
    • Year and Date
      2011-10-22
    • Related Report
      2011 Annual Research Report
  • [Presentation] Palladium -Catalyzed Synthesis of Organosilicon Compounds via Cycloaddition and Insertion of Silylene Equivalent Generated from Silylboronic Esters2011

    • Author(s)
      Toshimichi Ohmura, Kohei Masuda, Ichiro Takase, Michinori Suginome
    • Organizer
      The 16th IUPAC Iternational Symposium on Organometallic Chemistry Directed Towards OrganicSvnthesis
    • Place of Presentation
      上海(中国)
    • Year and Date
      2011-07-25
    • Related Report
      2012 Final Research Report
  • [Presentation] Palladium-Catalyzed Synthesis of Organosilicon Compounds via Cycloaddition and Insertion of Silylene Equivalent Generated from Silylboronic Esters2011

    • Author(s)
      Toshimichi Ohmura
    • Organizer
      The 16th IUPAC International Symposium on Organometallic Chemistry Directed Towards Organic Synthesis (OMCOS-16)
    • Place of Presentation
      Shanghai, China
    • Year and Date
      2011-07-25
    • Related Report
      2011 Annual Research Report
  • [Presentation] (アミノシリル)ボランとパラジウム触媒を用いる炭素-酸素結合へのシリレンの二重挿入によるジシラン生成2011

    • Author(s)
      大村智通
    • Organizer
      日本化学会第91春季年会
    • Place of Presentation
      日本化学会第91春季年会(2011)講演予稿集
    • Year and Date
      2011-03-11
    • Related Report
      2010 Annual Research Report
  • [Presentation] Silylboronic Esters Bearing a Dialkylamino Group on Silicon: New Silylene Equivalents for Palladium-Catalyzed C-Si Bond Formation2010

    • Author(s)
      Toshimichi Ohmura, Kohei Masuda, Ichiro Takase, Michinori Suginome
    • Organizer
      Pacifichem 2010
    • Place of Presentation
      ホノルル(アメリカ)
    • Year and Date
      2010-12-15
    • Related Report
      2012 Final Research Report
  • [Presentation] Silylboronic Esters Bearing a Dialkylamino Group on Silicon : New Silylene Equivalents for Palladium-Catalyzed C-Si Bond Formation2010

    • Author(s)
      Toshimichi Ohmura
    • Organizer
      Pacifichem 2010
    • Place of Presentation
      Honolulu, Hawaii(米国)
    • Year and Date
      2010-12-15
    • Related Report
      2010 Annual Research Report
  • [Presentation] ボリルシランをシリレン等価体として用いるパラジウム触媒シリレン挿入反応2010

    • Author(s)
      大村智通、高瀬一郎、増田幸平、杉野目道紀
    • Organizer
      第14回ケイ素化学協会シンポジウム
    • Place of Presentation
      ニューウェルシティー湯河原(静岡県
    • Year and Date
      2010-11-19
    • Related Report
      2012 Final Research Report
  • [Presentation] ボリルシランをシリレン等価体として用いるパラジウム触媒シリレン挿入反応2010

    • Author(s)
      大村智通
    • Organizer
      第14回ケイ素化学協会シンポジウム
    • Place of Presentation
      ニューウェルシティー湯河原(静岡県)
    • Year and Date
      2010-11-19
    • Related Report
      2010 Annual Research Report
  • [Presentation] 遷移金属触媒によるボリル化・シリル化の精密反応制御を鍵とする合成方開発2010

    • Author(s)
      大村智通
    • Organizer
      第27回有機合成化学セミナー
    • Place of Presentation
      シーサイドホテル舞子ビラ神戸(兵庫県)
    • Year and Date
      2010-09-03
    • Related Report
      2012 Final Research Report
  • [Presentation] 遷移金属触媒によるボリル化・シリル化の精密反応制御を鍵とする合成法開発2010

    • Author(s)
      大村智通
    • Organizer
      第27回有機合成化学セミナー
    • Place of Presentation
      シーサイドホテル舞子ビラ神戸(兵庫県)(招待講演)
    • Year and Date
      2010-09-03
    • Related Report
      2010 Annual Research Report
  • [Presentation] ホウ素反応剤を用いる遷移金属触媒反応の新展開

    • Author(s)
      大村智通(代表者)
    • Organizer
      第45回有機金属若手の会 夏の学校
    • Place of Presentation
      ホテルエバーグリーン富士(山梨県)
    • Related Report
      2012 Annual Research Report
    • Invited
  • [Presentation] Rhodium-Catalyzed Regioselective Hydroboration of Pyridines, Giving 1,2-Dihydropyridines

    • Author(s)
      Toshimichi Ohmura(代表者)、Kazuyuki Oshima、Michinori Suginome
    • Organizer
      XXV International Conference on Organometallic Chemistry (ICOMC2012)
    • Place of Presentation
      リスボン(ポルトガル)
    • Related Report
      2012 Annual Research Report
  • [Presentation] Transition-Metal-Catalyzed Synthetic Reactions Using Amino(boryl)silane as a Silylene Equivalent

    • Author(s)
      Toshimichi Ohmura(代表者)
    • Organizer
      The 4th Asian Silicon Symposium (ASiS-4)
    • Place of Presentation
      つくば国際会議場(つくば市)
    • Related Report
      2012 Annual Research Report
    • Invited
  • [Presentation] Dearomatizing Conversion of Nitrogen-Containing Aromatic Compounds via Addition Reactions of Boron Reagents

    • Author(s)
      Toshimichi Ohmura(代表者)
    • Organizer
      The 2nd International Kyoto Symposium on Organic Nanostructures (IKSON-2)
    • Place of Presentation
      京都大学桂キャンパス(京都市)
    • Related Report
      2012 Annual Research Report
  • [Book] Reagents for Silicon-Mediated Organic Synthesis, Handbook of Reagents for Organic Synthesis2011

    • Author(s)
      Toshimich Ohmura, Michinori Suginome
    • Publisher
      Wiley-VCH
    • Related Report
      2012 Final Research Report
  • [Book] Boronic Acids Second Edition2011

    • Author(s)
      Michinori Suginome, Toshimich Ohmura
    • Publisher
      Wiley-VCH
    • Related Report
      2012 Final Research Report
  • [Book] Boronic Acids, Second Edition2011

    • Author(s)
      Michinori Suginome, Toshimichi Ohmura
    • Publisher
      Wiley-VCH
    • Related Report
      2011 Annual Research Report
  • [Book] Handbook of Reagents for Organic Synthesis, Reagents for Silicon-Mediated Organic Synthesis2011

    • Author(s)
      Toshimichi Ohmura, Michinori Suginome
    • Publisher
      Wiley
    • Related Report
      2011 Annual Research Report
  • [Remarks]

    • Related Report
      2012 Final Research Report
  • [Remarks] 研究室ホームページ

    • URL

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

    • Related Report
      2012 Annual Research Report
  • [Remarks]

    • URL

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

    • Related Report
      2011 Annual Research Report
  • [Remarks]

    • URL

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

    • Related Report
      2010 Annual Research Report

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Published: 2010-08-23   Modified: 2019-07-29  

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