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Development and Application of Cyanofunctionalization Reactions across Unsaturated Bonds

Research Project

Project/Area Number 21685023
Research Category

Grant-in-Aid for Young Scientists (A)

Allocation TypeSingle-year Grants
Research Field Organic industrial materials
Research InstitutionKyoto University

Principal Investigator

NAKAO Yoshiaki  京都大学, 大学院・工学研究科, 講師 (60346088)

Project Period (FY) 2009 – 2011
Project Status Completed (Fiscal Year 2011)
Budget Amount *help
¥27,950,000 (Direct Cost: ¥21,500,000、Indirect Cost: ¥6,450,000)
Fiscal Year 2011: ¥5,720,000 (Direct Cost: ¥4,400,000、Indirect Cost: ¥1,320,000)
Fiscal Year 2010: ¥5,720,000 (Direct Cost: ¥4,400,000、Indirect Cost: ¥1,320,000)
Fiscal Year 2009: ¥16,510,000 (Direct Cost: ¥12,700,000、Indirect Cost: ¥3,810,000)
Keywords遷移金属 / 不飽和化合物 / シアノ官能基化反応
Research Abstract

The cooperative catalysis by palladium and triphenylborane effects the intramolecular oxycyanation and aminocyanation of alkenes through the cleavage of O-CN bonds and the subsequent insertion of double bonds. The use of 4, 5-bis(diphenylphosphino)-9, 9dimethylxanthene(Xantphos) as a ligand for palladium is essential for allowing the transformation to proceed with high chemo and regioselectivity. Variously substituted dihydrobenzofurans with both a tetrasubstituted carbon and cyano functionality, which are often found in biologically active substances including some pharmaceuticals, are accessed by the newly developed methodology in a highly efficient manner.

Report

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

    (14 results)

All 2012 2011 2010 2009

All Journal Article (8 results) (of which Peer Reviewed: 8 results) Presentation (6 results)

  • [Journal Article] Intermolecular Oxycyanation of Alkenes by Cooperative Pd/BPh_3 Catalysis2012

    • Author(s)
      デニスコスター, 小林昌登, ダニエルヴエルツ, 中尾佳亮
    • Journal Title

      Journal of the American Chemical Society

      Volume: 134巻 Issue: 15 Pages: 6544-6547

    • DOI

      10.1021/ja301375c

    • Related Report
      2011 Annual Research Report 2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] Nickel/Lewis Acid catalyzed Aryland Alkenylcyanation of Unsaturated Bonds2010

    • Author(s)
      矢田陽, 江畑志郎, 出井宏明, 中尾佳亮, 檜山爲次郎
    • Journal Title

      Bulletin of the Chemical Society of Japan

      Volume: 83巻 Issue: 10 Pages: 1170-1184

    • DOI

      10.1246/bcsj.20100068

    • NAID

      130004058986

    • Related Report
      2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] Nickel/Lewis Acidcatalyzed Cyanoesterification and Cyanocarbamoylation of Alkynes2010

    • Author(s)
      平田泰啓, 矢田陽, 中尾佳亮, 檜山爲次郎, 大橋理人, 生越専介
    • Journal Title

      Journal of the American Chemical Society

      Volume: 132巻 Issue: 29 Pages: 10070-10077

    • DOI

      10.1021/ja102346v

    • Related Report
      2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] Heteroatom directed Alkylcyanation of Alkynes2010

    • Author(s)
      中尾佳亮, 矢田陽, 檜山爲次郎
    • Journal Title

      Journal of the American Chemical Society

      Volume: 132巻 Issue: 29 Pages: 10024-10026

    • DOI

      10.1021/ja1017078

    • Related Report
      2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] Asymmetric Synthesis of Indolines Bearinga Benzylic Quaternary Stereocenterthrough Intramolecular Arylcyanation of Alkenes2010

    • Author(s)
      謝仁傑, 中尾佳亮, 檜山爲次郎
    • Journal Title

      Synlett

      Volume: 2010 Issue: 11 Pages: 1709-1711

    • DOI

      10.1055/s-0029-1219964

    • Related Report
      2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] Asymmetric Synthesis of Indolines Bearing a Benzylic Quaternary Stereocenter through Intramolecular Arylcyanation of Alkenes2010

    • Author(s)
      J.-C.Hsieh, Y.Nakao, T.Hiyama
    • Journal Title

      Synlett

      Pages: 1709-1711

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Heteroatom-directed Alkylcyanation of Alkynes2010

    • Author(s)
      Y.Nakao, A.Yada, T.Hiyama
    • Journal Title

      J.Am.Chem.Soc.

      Volume: 132 Pages: 10024-10026

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Nickel/Lewis Acid-catalyzed Cyanoesterification and Cyanocarbamoylation of Alkynes2010

    • Author(s)
      Y.Hirata, A.Yada, E.Morita, Y.Nakao, T.Hiyama, M.Ohashi, S.Ogoshi
    • Journal Title

      J.Am.Chem.Soc.

      Volume: 132 Pages: 10070-10077

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Presentation] 不飽和化合物のカルボシアノ化反応の研究2012

    • Author(s)
      中尾佳亮
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      慶応義塾大学日吉キャンパス
    • Year and Date
      2012-03-27
    • Related Report
      2011 Final Research Report
  • [Presentation] Carbocyanation Reaction of Unsaturated Bonds2011

    • Author(s)
      中尾佳亮
    • Organizer
      2nd International Collaborative and Cooperative Chemistry Symposium
    • Place of Presentation
      クィーンズ大学
    • Year and Date
      2011-10-31
    • Related Report
      2011 Final Research Report
  • [Presentation] Carbocyanation Reaction of Unsaturated Bonds2011

    • Author(s)
      Yoshiaki Nakao
    • Organizer
      2nd International Collaborative and Cooperative Chemistry Symposium
    • Place of Presentation
      Brisbane, Australia(招待講演)
    • Year and Date
      2011-10-31
    • Related Report
      2011 Annual Research Report
  • [Presentation] Carbocyanation Reaction of Unsaturated Bonds2010

    • Author(s)
      中尾佳亮
    • Organizer
      18th International Conferenceon Organic Synthesis
    • Place of Presentation
      ベルゲン
    • Year and Date
      2010-08-02
    • Related Report
      2011 Final Research Report
  • [Presentation] 協働金属触媒による炭素-炭素結合形成付加反応2010

    • Author(s)
      中尾佳亮
    • Organizer
      第22回万有札幌シンポジウム
    • Place of Presentation
      札幌(招待講演)
    • Year and Date
      2010-07-03
    • Related Report
      2010 Annual Research Report
  • [Presentation] C-C Bond Forming Addition Reactions by Nickel/Lewis Acid Catalysis2009

    • Author(s)
      Yoshiaki Nakao
    • Organizer
      Rising Organic Chemists in Catalysis
    • Place of Presentation
      Munster, Germany
    • Year and Date
      2009-06-18
    • Related Report
      2009 Annual Research Report

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

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