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Development of Highly Efficient Synthesis of Organoboron Compounds

Research Project

Project/Area Number 21350049
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Research Field Synthetic chemistry
Research InstitutionHokkaido University

Principal Investigator

ISHIYAMA Tatsuo  北海道大学, 大学院・工学研究院, 准教授 (00232348)

Co-Investigator(Renkei-kenkyūsha) YAMAMOTO Yasunori  北海道大学, 大学院・工学研究院, 助教 (30271646)
Project Period (FY) 2009 – 2011
Project Status Completed (Fiscal Year 2011)
Budget Amount *help
¥18,330,000 (Direct Cost: ¥14,100,000、Indirect Cost: ¥4,230,000)
Fiscal Year 2011: ¥4,680,000 (Direct Cost: ¥3,600,000、Indirect Cost: ¥1,080,000)
Fiscal Year 2010: ¥6,500,000 (Direct Cost: ¥5,000,000、Indirect Cost: ¥1,500,000)
Fiscal Year 2009: ¥7,150,000 (Direct Cost: ¥5,500,000、Indirect Cost: ¥1,650,000)
Keywords有機ホウ素化合物 / 炭素-水素結合活性化 / ホウ素化 / 遷移金属触媒 / ビニル型ホウ素化合物 / イリジウム触媒 / 環状ビニルエーテル / ベンジル型ホウ素化合物 / C-H結合活性化 / C-H結合直接ホウ素化 / アルキルベンゼン / ジボロン / ヒドロボラン / パラジウム触媒 / アリール型ホウ素化合物 / 芳香族化合物 / ビピリジン配位
Research Abstract

Organoboron compounds are an important class of compounds that have been utilized as synthetic intermediates, functional molecules, functional polymers, 10B carriers for neutron capture therapy, and biologically active compounds. For the synthesis of them, direct borylation of unreactive C-H bonds catalyzed by transition metal complexes is one of the most economical, efficient, elegant, and environmentally benign protocols. We found that Ir-and Pd-catalyzed C-H borylation of arenes heteroarenes, alkenes, and benzylic positions of alkylarenes by bis(pinacolato)diboron or pinacolborane provided aryl-, heteroaryl-alkenyl, and benzylboron compounds, respectively.

Report

(4 results)
  • 2011 Annual Research Report   Final Research Report ( PDF )
  • 2010 Annual Research Report
  • 2009 Annual Research Report
  • Research Products

    (46 results)

All 2012 2011 2010 2009 2008 Other

All Journal Article (15 results) (of which Peer Reviewed: 15 results) Presentation (21 results) Book (2 results) Remarks (4 results) Patent(Industrial Property Rights) (4 results)

  • [Journal Article] Iridium-catalyzed ortho-C-H borylation of aryl ketones with bis(pinacolato)diboron2011

    • Author(s)
      Hiroshi Itoh、Takao Kikuchi、Tatsuo Ishiyama and Norio Miyaura
    • Journal Title

      Chem. Lett

      Volume: 40 Pages: 1007-1008

    • NAID

      10029522609

    • Related Report
      2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of tetra-ortho-substituted biaryls using aryltriolborates2011

    • Author(s)
      Gao-Qiang Li、Yasunori Yamamoto and Norio Miyaura
    • Journal Title

      Synlett

      Pages: 1769-1773

    • NAID

      120005946643

    • Related Report
      2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] Double-coupling of dibromo arenes with aryltriolborates for synthesis of diaryl-substituted planar frameworks2011

    • Author(s)
      Gao-Qiang Li、Yasunori Yamamoto and Norio Miyaura
    • Journal Title

      Tetrahedron

      Volume: 67 Pages: 6804-6811

    • NAID

      120003370692

    • Related Report
      2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] Direct conversion of pinacol arylboronic esters to aryl triolborates2011

    • Author(s)
      Gao-Qiang Li、Shunsuke Kiyomura、 Yasunori Yamamoto and Norio Miyaura
    • Journal Title

      Chem. Lett

      Volume: 40 Pages: 702-704

    • NAID

      10029280526

    • Related Report
      2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] Ru/Me-BIPAM-catalyzed asymmetric addition of arylboronic acids to aliphatic aldehydes and α -keto esters2011

    • Author(s)
      Yasunori Yamamoto、Tomohiko Shirai、Gao-Qiang Li、Shunsuke Kiyomura、Tomohiko Shirai、Momoko Watanabe、Kazunori Kurihara and Norio Miyaura
    • Journal Title

      Molecules

      Volume: 16 Pages: 5020-5034

    • Related Report
      2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] Rhodium-catalyzed 1,4-addition of lithium 2-furyltriolborates to unsaturated ketones and esters for enantioselective synthesis of γ -oxo-carboxylic acids by oxidation of the furyl ring with ozone2011

    • Author(s)
      Xiao-Qiang Yu、Tomohiko Shirai、 Yasunori Yamamoto and Norio Miyaura
    • Journal Title

      Chem. Asian J

      Volume: 6 Pages: 932-937

    • Related Report
      2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] Iridium-Catalyzed ortho-C-H Borylation of Aryl Ketones with Bis(pinacolato)diboron2011

    • Author(s)
      H.Itoh, T.Kikuchi, T.Ishiyama, N.Miyaura
    • Journal Title

      Chem.Lett.

      Volume: 40 Issue: 9 Pages: 1007-1008

    • DOI

      10.1246/cl.2011.1007

    • NAID

      10029522609

    • Related Report
      2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Ortho-C-H borylation of benzoate esters with bis(pinacolato)diboron catalyzed by iridium-phosphine complexes2010

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

      Chem. Commun

      Volume: 46 Pages: 159-161

    • NAID

      120002695774

    • Related Report
      2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] Palladium-catalyzed cross-coupling reaction of heteroaryltriolborates with aryl halides for synthesis of biaryls2010

    • Author(s)
      Yasunori Yamamoto、Miho Takizawa、Xiao-Qiang Yu and Norio Miyaura
    • Journal Title

      Heterocycles

      Volume: 80 Pages: 359-368

    • NAID

      120002834748

    • Related Report
      2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] Ortho-C-H borylation of benzoate esters with bis(pinacolato)diboron Catalyzed by iridium phosphine complexes2010

    • Author(s)
      T.Ishiyama, H.Isou, T.Kikuchi N.Miyaura
    • Journal Title

      Chemical Communications 46

      Pages: 159-161

    • NAID

      120002695774

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Me-bipam for Enantioselective Ruthenium(II)-Catalyzed Arylation of Aldehydes with Arylboronic Acids、Angew2009

    • Author(s)
      Yasunori Yamamoto、Kazunori Kurihara and Norio Miyaura
    • Journal Title

      Chem. Int. Ed

      Volume: 48 Pages: 4414-4416

    • Related Report
      2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] Rhodium-catalyzed asymmetric 1,4-addition of heteroaryl cyclic triolborate toα, β -unsaturated carbonyl compounds2009

    • Author(s)
      Xiao-Qiang Yu、Yasunori Yamamoto and Norio Miyaura
    • Journal Title

      Synlett

      Pages: 994-998

    • Related Report
      2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] A chiral bidentate phosphoramidite (Me-BIPAM) for Rh-catalyzed asymmetric hydrogenation of α-dehydroamino esters, enamides, and dimethyl itaconate2009

    • Author(s)
      Kazunori Kurihara、Yasunori Yamamoto and Norio Miyaura
    • Journal Title

      TetrahedronLett

      Volume: 50 Pages: 3158-3160

    • Related Report
      2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] An N-linked bidentate phosphoramidite ligand (N-Me-BIPAM) for rhodium-catalyzed asymmetric addition of arylboronic acids to N-sulfonylarylaldimines、Adv2009

    • Author(s)
      Kazunori Kurihara、Yasunori Yamamoto and Norio Miyaura
    • Journal Title

      Synth. Cat

      Volume: 351 Pages: 260-270

    • Related Report
      2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] γ -Selective Cross-Coupling Reactions of Potassium Allyltrifluoroborates with Haloarenes Catalyzed by a Pd(0)/D-t-BPF or Pd(0)/Josiphos ((R, S)-CyPF-t-Bu) Complex : Mechanistic Studies on Transmetalation and Enantioselection2009

    • Author(s)
      Yasunori Yamamoto、Shingo Takada、Norio Miyaura、Tetsuji Iyama and Hiroto Tachikawa
    • Journal Title

      Organometallics

      Volume: 28 Pages: 152-160

    • Related Report
      2011 Final Research Report
    • Peer Reviewed
  • [Presentation] リジウム/アルシン系触媒を用いたカルボニル基を有するヘテロアレーンの位置選択的なC-Hホウ素化反2012

    • Author(s)
      開翔太郎、石山竜生、宮浦憲夫、伊藤肇
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      慶応義塾大学(横浜市)
    • Year and Date
      2012-03-25
    • Related Report
      2011 Annual Research Report
  • [Presentation] イリジウム触媒を用いたジボロンによる芳香族アルジミンのオルト位C-Hホウ素化反応2012

    • Author(s)
      天羽龍之介、石山竜生、伊藤肇
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      慶応義塾大学(横浜市)
    • Year and Date
      2012-03-25
    • Related Report
      2011 Annual Research Report
  • [Presentation] リジウム/アルシン系触媒を用いたカルボニル基を有するヘテロアレーンの位置選択的なC-Hホウ素化反応2012

    • Author(s)
      開翔太郎、石山竜生、宮浦憲夫、伊藤肇
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      横浜
    • Related Report
      2011 Final Research Report
  • [Presentation] イリジウム触媒を用いたジボロンによる芳香族アルジミンのオルト位C-Hホウ素化反応2012

    • Author(s)
      天羽龍之介、伊藤肇、石山竜生
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      横浜
    • Related Report
      2011 Final Research Report
  • [Presentation] パラジウム/Josiphos触媒によるシリルケテンアセタールの不斉アリール化反応におけるトランスメタル化および不斉発現機構2012

    • Author(s)
      小林謙也、伊藤肇、山本靖典
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      横浜
    • Related Report
      2011 Final Research Report
  • [Presentation] ルテニウム/Me-BIAPAM錯体を用いるアリールボロン酸のイサチン類への不斉付加反応2012

    • Author(s)
      養王田昌昭、白井智彦、伊藤肇、山本靖典
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      横浜
    • Related Report
      2011 Final Research Report
  • [Presentation] 大学院総合化学院における有機化学系講義の現況について2011

    • Author(s)
      石山竜生
    • Organizer
      平成23年度工学教育研究講演会
    • Place of Presentation
      北海道大学(札幌市)
    • Year and Date
      2011-09-09
    • Related Report
      2011 Annual Research Report
  • [Presentation] Ru/Me-BIPAM触媒によるアリールボロン酸のグリオキシル酸エステルおよびイサチン類への不斉付加反応2011

    • Author(s)
      白井智彦、伊藤肇、山本靖典
    • Organizer
      第58回有機金属化学討論会
    • Place of Presentation
      名古屋
    • Related Report
      2011 Final Research Report
  • [Presentation] イミン類に対するアリールボロン酸の不斉付加反応によるアリールグリシン誘導体の合成2011

    • Author(s)
      高橋良徳、栗原一典、山本靖典、宮浦憲夫
    • Organizer
      日本化学会第91春季年会
    • Place of Presentation
      横浜
    • Related Report
      2011 Final Research Report
  • [Presentation] イリジウム触媒を用いたフルオロジシランによるヘテロアレーン類の芳香族C-Hシリル化における反応効率の改善2010

    • Author(s)
      岩口祐典、石山竜生、宮浦憲夫
    • Organizer
      日本化学会第90春季年会
    • Place of Presentation
      近畿大学大阪
    • Year and Date
      2010-03-26
    • Related Report
      2009 Annual Research Report
  • [Presentation] Ru/Me-BIPAM触媒によるアリールボロン酸のアルデヒドおよびα-ケトエステルへのエナンチオ選択的アリール化反応2010

    • Author(s)
      白井智彦、渡辺桃子、栗原一典、山本靖典、宮浦憲夫
    • Organizer
      第57回有機金属化学討論会
    • Place of Presentation
      東京
    • Related Report
      2011 Final Research Report
  • [Presentation] パラジウム/Josiphos錯体で触媒されるケテンシリルアセタールのエナンチオ選択的α-アリール化反応2010

    • Author(s)
      小林謙也、山本靖典、宮浦憲夫
    • Organizer
      第57回有機金属化学討論会
    • Place of Presentation
      東京
    • Related Report
      2011 Final Research Report
  • [Presentation] イリジウム触媒を用いたフルオロジシランによるヘテロアレーン類の芳香族C-Hシリル化における反応効率の改善2010

    • Author(s)
      岩口祐典、石山竜生、宮浦憲夫
    • Organizer
      日本化学会第90春季年会
    • Place of Presentation
      東大阪
    • Related Report
      2011 Final Research Report
  • [Presentation] ルテニウム/Me-BIPAM錯体を用いるアリールボロン酸のα-ケトエステルへの不斉付加反応2010

    • Author(s)
      白井智彦、栗原一典、山本靖典、宮浦憲夫
    • Organizer
      日本化学会第90春季年会
    • Place of Presentation
      東大阪
    • Related Report
      2011 Final Research Report
  • [Presentation] パラジウム/Josiphos錯体を用いる,シリルケテンアセタールの不斉アリール化2010

    • Author(s)
      小林謙也、山本靖典、宮浦憲夫
    • Organizer
      日本化学会第90春季年会
    • Place of Presentation
      東大阪
    • Related Report
      2011 Final Research Report
  • [Presentation] 有機トリオールボレートを用いたオルト四置換ビアリールの合成2010

    • Author(s)
      李高強、山本靖典、宮浦憲夫
    • Organizer
      日本化学会第90春季年会
    • Place of Presentation
      東大阪
    • Related Report
      2011 Final Research Report
  • [Presentation] Iridium-Catalyzed ortho-Borylation of Aryl Ketones with Bis(pinacolato)diboron2009

    • Author(s)
      H.Itoh, T.Kikuchi, T.Ishiyama, Norio Miyaura
    • Organizer
      56^<th> Symposium on Organometallic Chemstry, Japan
    • Place of Presentation
      Doshisha University Kyoto
    • Year and Date
      2009-09-10
    • Related Report
      2009 Annual Research Report
  • [Presentation] イリジウム触媒を用いたビス(ピナコラート)ジボロンによる芳香族ケトンのオルト位ホウ素化反応2009

    • Author(s)
      伊藤啓司、菊池貴夫、石山竜生、宮浦憲夫
    • Organizer
      日本化学会北海道支部2009年夏季研究発表会
    • Place of Presentation
      苫小牧工業高等専門学校苫小牧
    • Year and Date
      2009-07-11
    • Related Report
      2009 Annual Research Report
  • [Presentation] イリジウム触媒を用いたアリールケトンのビス(ピナコラート)ジボロンによるオルト位ホウ素化反応2009

    • Author(s)
      伊藤啓司、菊池貴夫、石山竜生、宮浦憲夫
    • Organizer
      第56回有機金属化学討論会
    • Place of Presentation
      京都
    • Related Report
      2011 Final Research Report
  • [Presentation] ルテニウム/Me-BIPAM錯体によるアリールボロン酸のアルデヒドへの不斉1,2-付加反応2009

    • Author(s)
      山本靖典、栗原一典、宮浦憲夫
    • Organizer
      第56回有機金属化学討論会
    • Place of Presentation
      京都
    • Related Report
      2011 Final Research Report
  • [Presentation] ヘテロ芳香族環状トリオールボレート塩のロジウム触媒不斉1,4-付加反応2009

    • Author(s)
      于暁強、白井智彦、山本靖典、宮浦憲夫
    • Organizer
      第56回有機金属化学討論会
    • Place of Presentation
      京都
    • Related Report
      2011 Final Research Report
  • [Book] 使える!有機合成反応241実践ガイド2010

    • Author(s)
      石山竜生
    • Publisher
      化学同人
    • Related Report
      2011 Final Research Report
  • [Book] 使える 有機合成反応241 実践ガイド2010

    • Author(s)
      石山竜生
    • Total Pages
      4
    • Publisher
      化学同人
    • Related Report
      2010 Annual Research Report
  • [Remarks]

    • URL

      http://labs.eng.hokudai.ac.jp/labo/organoelement/

    • Related Report
      2011 Final Research Report
  • [Remarks]

    • URL

      http://labs.eng.hokudai.ac.jp/labo/organoelement/

    • Related Report
      2011 Annual Research Report
  • [Remarks]

    • URL

      http://labs.eng.hokudai.ac.jp/labo/organoelement/

    • Related Report
      2010 Annual Research Report
  • [Remarks]

    • URL

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

    • Related Report
      2009 Annual Research Report
  • [Patent(Industrial Property Rights)] B-アリールボラジンの製造方法2010

    • Inventor(s)
      宮浦憲夫、山本靖典
    • Industrial Property Rights Holder
      株式会社日本触媒
    • Acquisition Date
      2010-12-16
    • Related Report
      2011 Final Research Report
  • [Patent(Industrial Property Rights)] B-アリールボラジンの製造方法2009

    • Inventor(s)
      宮浦憲夫、山本靖典
    • Industrial Property Rights Holder
      株式会社日本触媒
    • Filing Date
      2009-06-08
    • Related Report
      2011 Final Research Report
  • [Patent(Industrial Property Rights)] ピナコールボランの製造方法2009

    • Inventor(s)
      宮浦憲夫、山本靖典
    • Industrial Property Rights Holder
      国立大学法人北海道大学
    • Acquisition Date
      2009-08-27
    • Related Report
      2011 Final Research Report
  • [Patent(Industrial Property Rights)] ピナコールボランの製造方法2008

    • Inventor(s)
      宮浦憲夫、山本靖典
    • Industrial Property Rights Holder
      国立大学法人北海道大学
    • Filing Date
      2008-02-15
    • Related Report
      2011 Final Research Report

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Published: 2009-04-01   Modified: 2016-04-21  

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