• Search Research Projects
  • Search Researchers
  • How to Use
  1. Back to previous page

Development of Novel Synthetic Method using C-H and C-Heteroatom bond Functionalization

Research Project

Project/Area Number 20350019
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Research Field Organic chemistry
Research InstitutionKyoto University

Principal Investigator

MATSUBARA Seijiro  京都大学, 大学院・工学研究科, 教授 (90190496)

Co-Investigator(Kenkyū-buntansha) KURAHASHI Takuya  京都大学, 大学院・工学研究科, 助教 (50432365)
Project Period (FY) 2008 – 2010
Project Status Completed (Fiscal Year 2010)
Budget Amount *help
¥18,460,000 (Direct Cost: ¥14,200,000、Indirect Cost: ¥4,260,000)
Fiscal Year 2010: ¥4,680,000 (Direct Cost: ¥3,600,000、Indirect Cost: ¥1,080,000)
Fiscal Year 2009: ¥4,680,000 (Direct Cost: ¥3,600,000、Indirect Cost: ¥1,080,000)
Fiscal Year 2008: ¥9,100,000 (Direct Cost: ¥7,000,000、Indirect Cost: ¥2,100,000)
Keywords複素環 / ニッケル / 環化付加 / アルキル鎖 / 銅触媒反応 / Mannich反応 / Click反応 / 付加反応 / C-H結合活性 / C-N給合活性 / カルボアミノヒ / カルボエーテル化 / 複素環化合物 / メタラサイクル / 脱カルボニル / C-H結合活性化 / 触媒 / 環化反応 / カルボアミノ化 / アルキン / 原子効率
Research Abstract

A nickelacycle, which was formed from easily available carbonyl compounds and nickel(0) via oxidative insertion and decarbonylation, added to an alkyne to produce the corresponding heterocyclic compound. It was found that phthalic imide gives tha isoquinolone ; phthalic anhydride gives the isochromenone.

Report

(4 results)
  • 2010 Annual Research Report   Final Research Report ( PDF )
  • 2009 Annual Research Report
  • 2008 Annual Research Report
  • Research Products

    (27 results)

All 2011 2010 2009 2008 Other

All Journal Article (17 results) (of which Peer Reviewed: 17 results) Presentation (5 results) Book (1 results) Remarks (4 results)

  • [Journal Article] Nickel-catalyzed Decarbonylative Cycloaddition of Phthalic Anhydrides with 1,3-Dienes2011

    • Author(s)
      Seijiro Matsubara
    • Journal Title

      Chemistry Letters

      Volume: 40 Pages: 322-323

    • NAID

      10027816079

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Nickel-catalyzed[2+ 2+ 1] Cycloaddition of Alkynes, Acrylates and Isocyanates2010

    • Author(s)
      T. Ozawa, T. Kutahashi, S. Matsubara
    • Journal Title

      Chem. Commun.

      Volume: 46巻 Pages: 8055-8057

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Selective synthesis of trienes and dienes vianickel-catalyzed intermolecular cotrimerization of acrylates and alkyne2010

    • Author(s)
      H. Horie, T. Kutahashi, S. Matsubara
    • Journal Title

      Chem. Commun.

      Volume: 46巻 Pages: 7229-7231

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Decarbonylative Cycloaddition of Phthalimides with 1, 3-Dienes2010

    • Author(s)
      K. Fujiwara, T. Kutahashi, S. Matsubara
    • Journal Title

      Org. Lett.

      Volume: 12巻 Pages: 4548-4551

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Effects of a Flexible Alkyl Chain on an Imidazole Ligand for Copper-Catalyzed Mannich Reactions of Terminal Alkynes2010

    • Author(s)
      Seijiro Matsubara
    • Journal Title

      Synlett

      Volume: 20 Pages: 3053-3056

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Effects of a Flexible Alkyl Chain on a Ligand for CuAAC Reaction2010

    • Author(s)
      Seijiro Matsubara
    • Journal Title

      Organic Letters

      Volume: 12 Pages: 4988-4991

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] A Tandem Reaction Initiated by 1,4-Addition of Bis (iodozincio) methane for 1,3-Diketone Formation2010

    • Author(s)
      Mutsumi Sada, Seijiro Matsubara
    • Journal Title

      Journal of the American Chemical Society 132

      Pages: 432-433

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Nickel-Catalyzed[4+ 2] Cycloaddition of Enones with Alkynes2009

    • Author(s)
      I. Koyama, T. Kutahashi, S. Matsubara
    • Journal Title

      J. Am. Chem. Soc.

      Volume: 131巻 Pages: 1350-1351

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Nickel-Catalyzed Decarboxylative Carboamination of Alkynes with Isatoic Anhydrides2009

    • Author(s)
      Y. Yoshino, T. Kutahashi, S. Matsubara
    • Journal Title

      J. Am. Chem. Soc.

      Volume: 131巻 Pages: 7494-7495

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Nickel-Catalyzed Cycloaddition of Salicylic Acid Ketals to Alkynes via Elimination of Ketones2009

    • Author(s)
      A. Ooguri, K. Nakai, T. Kutahashi, S. Matsubara
    • Journal Title

      J. Am. Chem. Soc.

      Volume: 131巻 Pages: 13194-13195

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Amphiphilic Organocatalyst for Schotten-Baumann-Type Tosylation of Alcohols under Organic Solvent Free Condition2009

    • Author(s)
      Keisuke Asano, Seijiro Matsubara
    • Journal Title

      Organic Letters 11

      Pages: 1757-1759

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Zincate-mediated rearrangement reaction of 2-(1-hydroxyalkyl)-1-alkylcyclopropanol2009

    • Author(s)
      Kenichi Nomura, Seijiro Matsubara
    • Journal Title

      Chemical Communication

      Pages: 2212-2213

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Nickel-Catalyzed Decarbonylative Addition of Anhydrides to Alkynes2008

    • Author(s)
      Y. Kajita, T. Kutahashi, S. Matsubara
    • Journal Title

      J. Am. Chem. Soc.

      Volume: 130巻 Pages: 17226-177227

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Nickel-Catalyzed Decarbonylative Addition of Phthalimides to Alkynes2008

    • Author(s)
      Y. Kajita, T. Kutahashi, S. Matsubara
    • Journal Title

      J. Am. Chem. Soc.

      Volume: 130巻 Pages: 6058-6059

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Nickel-Catalyzed Decarbonylative Addition of Anhydrides to Alkynes2008

    • Author(s)
      Y. Kajita, T. Kurahashi, S. Matsubara
    • Journal Title

      J. Am. Chein. Soc. 130

      Pages: 17226-17227

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Nickel-catalyzed decarbonylative addition of phthalimides to alkynes2008

    • Author(s)
      Y. Kajita, S. Matsubara, T. Kurahashi
    • Journal Title

      J. Am. Chem. Soc. 130

      Pages: 6058-6059

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Iron(II)chloride-mediated addition of dialkylmagnesium to carbonyl compounds2008

    • Author(s)
      M. Sada, S. Matsubara
    • Journal Title

      Cheni. Lett. 37

      Pages: 800-801

    • NAID

      10021082875

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Presentation] Tandem reaction initiated by 1, 4-addition of bis(iodozincio) methane for 1, 3-diketone formation2010

    • Author(s)
      Matsubara, S.
    • Organizer
      Pacificheme 2010, ID318
    • Place of Presentation
      Honolulu, USA
    • Year and Date
      2010-12-16
    • Related Report
      2010 Final Research Report
  • [Presentation] The new methods for the preparation of heterocyclic compounds2010

    • Author(s)
      Seijiro Matsubara
    • Organizer
      1st International Collaborative and Cooperative Chemistry Symposium
    • Place of Presentation
      National University of Singapore (Singapore)(招待講演)
    • Year and Date
      2010-11-16
    • Related Report
      2010 Annual Research Report
  • [Presentation] The new methods for the preparation of heterocyclic compounds2010

    • Author(s)
      Matsubara, S.
    • Organizer
      1st International Collaborative and Cooperative Chemistry Symposium
    • Place of Presentation
      National University of Singapore
    • Year and Date
      2010-11-15
    • Related Report
      2010 Final Research Report
  • [Presentation] A Novel Tandem Process Initiated by 1,4-Addition of Bis (iodozincio) methane for Selective 1,3-Diketone Formation2009

    • Author(s)
      Mutsumi Sada, Seijiro Matsubara
    • Organizer
      第15回国際純正・応用化学連合OMCOS会議
    • Place of Presentation
      英国・グラスゴー
    • Year and Date
      2009-07-27
    • Related Report
      2009 Annual Research Report
  • [Presentation] アルキンへの炭素-窒素または炭素-酸素結合の付加を用いた新規ヘテロ環化合物合成法の開発2008

    • Author(s)
      倉橋拓也, 松原誠二郎
    • Organizer
      第55回有機金属討論会
    • Place of Presentation
      大阪府立大中百舌鳥キャンパス
    • Year and Date
      2008-09-29
    • Related Report
      2008 Annual Research Report
  • [Book] 使える! 有機合成実線ガイド2010

    • Author(s)
      松原誠二郎
    • Total Pages
      8
    • Publisher
      化学同人
    • Related Report
      2009 Annual Research Report
  • [Remarks]

    • URL

      http://www.dfm.kuic.kyoto-u.ac.jp/Website/Welcome.html

    • Related Report
      2010 Final Research Report
  • [Remarks]

    • URL

      http://www.dfm.kuic.kyoto-u.ac.jp/Website/Welcome.html

    • Related Report
      2010 Annual Research Report
  • [Remarks]

    • URL

      http://www.dfm.kuic.kyoto-u.ac.jp/Website/Welcome.html

    • Related Report
      2009 Annual Research Report
  • [Remarks]

    • URL

      http://www.dfin.kuic.kyoto-u.ac.jp/Website/Publication.html

    • Related Report
      2008 Annual Research Report

URL: 

Published: 2008-04-01   Modified: 2016-04-21  

Information User Guide FAQ News Terms of Use Attribution of KAKENHI

Powered by NII kakenhi