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2008 Fiscal Year Final Research Report

INTRODUCTION OF BORYL OR SILYL GROUPS VIA AROMATIC OR ALIPHATIC CARBON-HYDROGEN BOND ACTIVATION

Research Project

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Project/Area Number 17065001
Research Category

Grant-in-Aid for Scientific Research on Priority Areas

Allocation TypeSingle-year Grants
Review Section Science and Engineering
Research InstitutionHokkaido University

Principal Investigator

ISHIYAMA Tatsuo  Hokkaido University, 大学院工学研究科, 准教授 (00232348)

Project Period (FY) 2005 – 2008
Keywords有機ホウ素化合物 / 有機ケイ素化合物 / 炭素-水素結合活性化 / ホウ素化 / ケイ素化 / 遷移金属触媒
Research Abstract

入手容易で安価な芳香族並びに脂肪族化合物の炭素-水素結合活性化を機軸とするジボロンやヒドロボランあるいはジシランやヒドロシランによる直接的なホウ素化反応およびケイ素化反応が、イリジウムなどの適当な遷移金属錯体を触媒として用いることにより進行することを明らかにした。これらの反応は、有機合成中間体、生理活性物質あるいは機能性分子として注目されている有機ホウ素およびケイ素化合物の経済的で環境調和型かつ効率的な合成法である。

  • Research Products

    (36 results)

All 2009 2008 2007 2006 2005 Other

All Journal Article (9 results) (of which Peer Reviewed: 9 results) Presentation (23 results) Book (2 results) Remarks (1 results) Patent(Industrial Property Rights) (1 results)

  • [Journal Article] Vinylic C-H borylation of cyclic vinyl ethers with bis(pinacolato)diboron catalyzed by an iridium(I)-dtbpy complex2008

    • Author(s)
      Takao Kikuchi, Jun Takagi, Hironori Isou, Tatsuo Ishiyama and Norio Miyaura
    • Journal Title

      Chem. Asian J 3

      Pages: 2082-2090

    • Peer Reviewed
  • [Journal Article] Iridium-catalyzed vinylic C-H borylation of cyclic vinyl ethers by bis(pinacolato)diboron2008

    • Author(s)
      Takao Kikuchi, Jun Takagi, Tatsuo Ishiyama and Norio Miyaura
    • Journal Title

      Chem. Lett 37

      Pages: 664-665

    • Peer Reviewed
  • [Journal Article] Practical synthesis of pinacolborane for one-pot synthesis of unsymmetrical biaryls via aromatic C-H borylation-cross-coupling sequence2008

    • Author(s)
      Takao Kikuchi, Yusuke Nobuta, Junko Umeda, Yasunori Yamamoto, Tatsuo Ishiyama and Norio Miyaura
    • Journal Title

      Tetrahedron 64

      Pages: 4967-4971

    • Peer Reviewed
  • [Journal Article] Improvements of efficiency and regioselectivity in the iridium(I)-catalyzed aromatic C-H silylation of arenes with fluorodisilanes2006

    • Author(s)
      Takeaki Saiki, Yukihiro Nishio, Tatsuo Ishiyama and Norio Miyaura
    • Journal Title

      Organometallics 25

      Pages: 6068-6073

    • Peer Reviewed
  • [Journal Article] Iridium-catalyzed borylation of arenes and heteroarenes via C-H activation2006

    • Author(s)
      Tatsuo Ishiyama and Norio Miyaura
    • Journal Title

      Pure Appl. Chem 78

      Pages: 1369-1375

    • Peer Reviewed
  • [Journal Article] Hartwig、Mechanism of the mild functionalization of arenes by diboron reagents catalyzed by iridium complexes. Intermediacy and chemistry of bipyridine-ligated iridium trisboryl complexes2005

    • Author(s)
      Timothy. M. Boller, Jaclyn M. Murphy, Marco Hapke, Tatsuo Ishiyama, Norio Miyaura and John F
    • Journal Title

      J. Am. Chem. Soc 127

      Pages: 14263-14278

    • Peer Reviewed
  • [Journal Article] Regioselective aromatic C-H silylation of five-membered heteroarenes with fluorodisilanes catalyzed by iridium(I) complexes2005

    • Author(s)
      Tatsuo Ishiyama, Kazuaki Sato, Yukihiro Nishio, Takeaki Saiki and Norio Miyaura
    • Journal Title

      Chem. Commun

      Pages: 5065-5067

    • Peer Reviewed
  • [Journal Article] Iridium-catalyzed C-H borylation of arenes and heteroarenes : 1-chloro-3-iodo-5-(4,4,5,5-tetrameth yl-1,3,2-dioxaborolan-2-yl)benzene and 2-(4,4,5,5,-tetramethyl-1,3,2-dioxab orolan-2-yl)indole2005

    • Author(s)
      Tatsuo Ishiyama, Jun Takagi, Yusuke Nobuta and Norio Miyaura
    • Journal Title

      Org. Synth 82

      Pages: 126-133

    • Peer Reviewed
  • [Journal Article] Transition metal-catalyzed direct borylation and silylation based on C-H activation2005

    • Author(s)
      Tatsuo Ishiyama
    • Journal Title

      J. Syth. Org. Chem., Jpn 63

      Pages: 440-452

    • Peer Reviewed
  • [Presentation] イリジウム触媒を用いたフルオロジシランによるビニル位C-H ケイ素化反応2009

    • Author(s)
      高田瑠美,岸田恵美,石山竜生,宮浦憲夫
    • Organizer
      日本化学会第89春季年会
    • Place of Presentation
      日本大学、船橋
    • Year and Date
      2009-03-30
  • [Presentation] Ortho-Borylation of Benzoate Esters with Diborons Catalyzed by Iridium Complexes2008

    • Author(s)
      Takao Kikuchi, Hironori Isou, Tatsuo Ishiyama and Norio Miyaura
    • Organizer
      55th Symposium on Organometallic Chemistry, Japan
    • Place of Presentation
      Osaka Prefecture University Osaka
    • Year and Date
      2008-09-29
  • [Presentation] Iridium-Catalyzed ortho-Borylation of Benzoate Esters by Diborons2008

    • Author(s)
      Tatsuo Ishiyama, Hironori Isou, Takao Kikuchi and Norio Miyaura
    • Organizer
      XIII International Conference on Boron Chemistry
    • Place of Presentation
      Palau d'Esports I Congressos、Platja d'Aro
    • Year and Date
      2008-09-23
  • [Presentation] Iridium-Catalyzed Aromatic C-H Silylation by 1-Hydrosilatrane2008

    • Author(s)
      Tatsuo Ishiyama and Norio Miyaura
    • Organizer
      Third International Conference on Advanced Organic Synthesis directed toward the Ultimate Efficiency and Practicability
    • Place of Presentation
      Otsu Prince Hotel、Otsu
    • Year and Date
      2008-05-27
  • [Presentation] イリジウム触媒を用いたジボロンによる安息香酸エステルのオルト位ホウ素化反応2008

    • Author(s)
      異相宏典,菊地貴夫,石山竜生,宮浦憲夫
    • Organizer
      日本化学会第88春季年会
    • Place of Presentation
      立教大学、東京
    • Year and Date
      2008-03-30
  • [Presentation] Iridium-Catalyzed Borylation of Cyclic Vinyl Ethers via Vinylic C-H Activation2008

    • Author(s)
      Takao Kikuchi, Tatsuo Ishiyama and Norio Miyaura
    • Organizer
      Catalysis as the Basis for the Innvation in Materials Science
    • Place of Presentation
      Hokkaido University、Sapporo
    • Year and Date
      2008-01-16
  • [Presentation] Iridium Catalyzed Aromatic C-H Borylation2008

    • Author(s)
      Tatsuo Ishiyama
    • Organizer
      1st Japan-Singapore Bilateral Symposium on Catalysis
    • Place of Presentation
      National University of Singapore、 Singapore
    • Year and Date
      2008-01-08
  • [Presentation] Iridium-Catalyzed Direct Silylation of Heteroarenes by 1-Hydrosilatrane2007

    • Author(s)
      Rumi Takata, Emi Kishida, Takeaki Saiki, Tatsuo Ishiyama and Norio Miyaura
    • Organizer
      54th Symposium on Organometallic Chemistry, Japan
    • Place of Presentation
      Hiroshima University
    • Year and Date
      2007-10-27
  • [Presentation] Iridium-Catalyzed Borylation of Cyclic Vinyl Ethers via Vinylic C-H Activation2007

    • Author(s)
      Takao Kikuchi, Tatsuo Ishiyama and Norio Miyaura
    • Organizer
      14th IUPAC International Symposium on Organometallic Chemistry diorected towards Organic Synthesis
    • Place of Presentation
      Nara Centennial Hall、Nara
    • Year and Date
      2007-08-03
  • [Presentation] イリジウム触媒を用いた 1-ヒドロシラトランによる芳香族C-H 結合の直接ケイ素化反応2007

    • Author(s)
      高田瑠美,岸田恵美,斎木丈章,石山竜生,宮浦憲夫
    • Organizer
      日本化学会北海道支部2007年夏季研究発表会
    • Place of Presentation
      旭川工業高等専門学校、旭川
    • Year and Date
      2007-07-21
  • [Presentation] Iridium-Catalyzed C-H Silylation of Heteroarenes by Fluorodisilanes2007

    • Author(s)
      Tatsuo Ishiyama and Norio Miyaura
    • Organizer
      International Conference on Asymmetric Organocatalysis
    • Place of Presentation
      Otsu Prince Hotel、Otsu
    • Year and Date
      2007-05-29
  • [Presentation] イリジウム触媒を用いるアレーンのC-H ホウ素化とケイ素化2007

    • Author(s)
      石山竜生
    • Organizer
      日本化学会第87春季年会
    • Place of Presentation
      関西大学千里山キャンパス、吹田
    • Year and Date
      2007-03-27
  • [Presentation] イリジウム触媒を用いた 1-ヒドロシラトランによるヘテロアレーン類の直接ケイ素化反応2007

    • Author(s)
      岸田恵美,高田瑠美,斎木丈章,石山竜生,宮浦憲夫
    • Organizer
      日本化学会第87春季年会
    • Place of Presentation
      関西大学千里山キャンパス、吹田
    • Year and Date
      2007-03-25
  • [Presentation] Aromatic C-H Silylation of Arenes with Fluorodisilanes Catalyzed by Iridiumu Complexes2006

    • Author(s)
      Tatsuo Ishiyama and Norio Miyaura
    • Organizer
      1st International Conference on Cutting-Edge Organic Chemistry in Asia
    • Place of Presentation
      Tiruru,Naha
    • Year and Date
      20061018-19
  • [Presentation] イリジウム触媒を用いたピナコールボランによる環状ビニルエーテルの脱水素-ホウ素化反応2006

    • Author(s)
      異相宏典,菊地貴夫,石山竜生,宮浦憲夫
    • Organizer
      第23回有機合成セミナー
    • Place of Presentation
      グリーンピア大沼、大沼
    • Year and Date
      20060913-15
  • [Presentation] Direct Silylation of Arenes with 1-Hydrosilatrane Catalyzed by Iridium Complexes2006

    • Author(s)
      Emi Kishida, Takeaki Saiki, Tatsuo Ishiyama, and Norio Miyaura
    • Organizer
      53rd Symposium on Organometallic Chemistry, Japan
    • Place of Presentation
      Osaka City University、Osaka
    • Year and Date
      20060907-09
  • [Presentation] Vinylic C-H Borylation of Cyclic Vinyl Ethers with Bis(pinacolato)diboron Catalyzed by Iridium Complexes2006

    • Author(s)
      Takao Kikuchi, Tatsuo Ishiyama and Norio Miyaura
    • Organizer
      XXII International Conference on Organometallic Chemistry
    • Place of Presentation
      Zaragoza University、Zaragoza、Spain
    • Year and Date
      20060723-28
  • [Presentation] イリジウム触媒を用いた環状ビニルエーテル類の直接ホウ素化反応2006

    • Author(s)
      菊地貴夫,石山竜生,宮浦憲夫
    • Organizer
      第18回万有札幌シンポジウム
    • Place of Presentation
      北海道厚生年金会館、札幌
    • Year and Date
      2006-07-08
  • [Presentation] イリジウム触媒を用いた1-ヒドロシラトランによるアレーン類の脱水素-ケイ素化反応2006

    • Author(s)
      斎木丈章,岸田恵美,石山竜生,宮浦憲夫
    • Organizer
      日本化学会第86春季年会
    • Place of Presentation
      日本大学船橋キャンパス、船橋
    • Year and Date
      2006-03-29
  • [Presentation] ビニル位C-H ホウ素化-クロスカップリング法によるC-アリールグリコシド類の簡便合成2006

    • Author(s)
      菊地貴夫,石山竜生,宮浦憲夫
    • Organizer
      日本化学会第86春季年会
    • Place of Presentation
      日本大学船橋キャンパス、船橋
    • Year and Date
      2006-03-29
  • [Presentation] Iridium-Catalyzed Vinylic C-H Borylation of Cyclic Vinyl Ethers by Bis(pinacolato)diboron2005

    • Author(s)
      Takao Kikuchi, Tatsuo Ishiyama and Norio Miyaura
    • Organizer
      52nd Symposium on Organometallic Chemistry, Japan
    • Place of Presentation
      Doshisha University、Kyoto
    • Year and Date
      20050915-16
  • [Presentation] Improvements of Efficiency and Regioselectivity in the Iridium(I)-Catalyzed Aromatic C-H Silylation of Arenes with Fluorodisilanes2005

    • Author(s)
      Takeaki Saiki, Yukihiro Nishio, Tatsuo Ishiyama and Norio Miyaura
    • Organizer
      52nd Symposium on Organometallic Chemistry, Japan
    • Place of Presentation
      Doshisha University、Kyoto
    • Year and Date
      20050915-16
  • [Presentation] Dehydrogenative Borylation of Aromatic Compounds with Pinacolborane Catalyzed by Iridium(I) Complexes at Room Temperature2005

    • Author(s)
      Tatsuo Ishiyama, John F. Hartwig and Norio Miyaura
    • Organizer
      12th International Conference on Boron Chemistry
    • Place of Presentation
      Aendai International Center、Sendai
    • Year and Date
      20050911-15
  • [Book] Handbook of C-H Transformations2005

    • Author(s)
      Tatsuo Ishiyama and Norio Miyaura
    • Total Pages
      126-131
    • Publisher
      Wiley-VCH
  • [Book] Boronic Acids2005

    • Author(s)
      Tatsuo Ishiyama and Norio Miyaura
    • Total Pages
      101-121
    • Publisher
      Wiley-VCH
  • [Remarks]

    • URL

      http://om-mc.eng.hokudai.ac.jp/indexj.html

  • [Patent(Industrial Property Rights)] 有機ケイ素化合物の製造方法2008

    • Inventor(s)
      宮浦憲夫,石山竜生,斎木丈章
    • Industrial Property Rights Holder
      東レ・ダウコーニング株式会社
    • Industrial Property Number
      特許公開, 2008-069076
    • Filing Date
      2008-03-27

URL: 

Published: 2010-06-10   Modified: 2016-04-21  

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