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Activation of Carbon-Carbon Bonds by Transition Metals

Research Project

Project/Area Number 19205013
Research Category

Grant-in-Aid for Scientific Research (A)

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

Principal Investigator

MURAKAMI Masahiro  Kyoto University, 大学院・工学研究科, 教授 (20174279)

Co-Investigator(Kenkyū-buntansha) MATSUDA Takanori  東京理科大学, 理学部, 講師 (80359778)
Project Period (FY) 2007 – 2009
Project Status Completed (Fiscal Year 2009)
Budget Amount *help
¥50,180,000 (Direct Cost: ¥38,600,000、Indirect Cost: ¥11,580,000)
Fiscal Year 2009: ¥12,740,000 (Direct Cost: ¥9,800,000、Indirect Cost: ¥2,940,000)
Fiscal Year 2008: ¥12,740,000 (Direct Cost: ¥9,800,000、Indirect Cost: ¥2,940,000)
Fiscal Year 2007: ¥24,700,000 (Direct Cost: ¥19,000,000、Indirect Cost: ¥5,700,000)
Keywords炭素-炭素結合切断 / 炭素-炭素結合形成 / 遷移金属触媒 / 白金 / 多環芳香族炭化水素 / アズレン / 不活性結合活性化 / 環化異性化反応 / ロジウム / シクロブタノール / インダノール / 骨格転位 / シクロブタノン / ニッケル
Research Abstract

New carbon-carbon bond cleaving reactions catalyzed by transition metals were developed. Various carbon skeletons were constructed by utilization of these reactions. In particular, enantioselective cleavage of a carbon-carbon bond led to the formation of quaternary chiral carbon centers. For example, six-membered benzolactones having a chiral quaternary center at the benzylic position were synthesized with high enantioselectivity. Indane skeletones having chiral quaternary centers at both benzylic positions were constructed in a stereoselective manner from cyclobutanols with an aryl substituent at the 3-position. A new method to synthesize azulene derivatives, which were attractive as organic materials, was also developed.

Report

(4 results)
  • 2009 Annual Research Report   Final Research Report ( PDF )
  • 2008 Annual Research Report
  • 2007 Annual Research Report
  • Research Products

    (23 results)

All 2009 2008 2007

All Journal Article (11 results) (of which Peer Reviewed: 11 results) Presentation (12 results)

  • [Journal Article] Stereoselective Restrucuring of 3-Arylcyclobutanols into 1-Indanols by Sequential Breaking and Formation of Carbon-Carbon Bonds2009

    • Author(s)
      Masanori Shigeno, Taiga Yamamoto, Masahiro Murakami
    • Journal Title

      Chem. Eur. J. 15

      Pages: 12929-12931

    • Related Report
      2009 Final Research Report
    • Peer Reviewed
  • [Journal Article] Nickel-Catalysed Denitrogenative Alkyne Insertion Reaction of N-Sulfony1-1, 2, 3-triazoles2009

    • Author(s)
      Tomoya Miura, Motoshi Yamauchi, Masahiro Murakami
    • Journal Title

      Chem. Commun.

      Pages: 1470-1471

    • Related Report
      2009 Final Research Report
    • Peer Reviewed
  • [Journal Article] Stereoselective Restrucuring of 3-Arylcyclobutanols into 1-Indanols by Sequential Breaking and Formation of Carbon-Carbon Bonds2009

    • Author(s)
      Masanori Shigeno, Taiga Yamamoto, Masahiro Murakami
    • Journal Title

      Chemistry-A European Journal 15

      Pages: 12929-12931

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Nickel-Catlyzed [4+2+2]-Type Annulation Reaction of Cyclobutanones with Diynes and Enynes2008

    • Author(s)
      Shinji Ashida, Masahiro Murakami
    • Journal Title

      Bull. Chem. Soc. Jpn. 81

      Pages: 885-893

    • Related Report
      2009 Final Research Report
    • Peer Reviewed
  • [Journal Article] Palladium-Catalyzed Sequential Carbon-Carbon Bond Cleavage/Formation Producing Arylated Benzolactones2008

    • Author(s)
      Takanori Matsuda, Masanori Shigeno, Masahiro Murakami
    • Journal Title

      Organic Letters 10

      Pages: 5219-5221

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of 1(2H)-Isoquinolones by the Nickel-Catalyzed Denitrogenative Alkyne Insertion of 1, 2, 3-Benzotriazin-4(3H)-ones2008

    • Author(s)
      Tomoya Miura, Motoshi Yamauchi, Masahiro Murakami
    • Journal Title

      Organic Letters 10

      Pages: 3085-3088

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Nickel-Catlyzed[4+2+2-]-Type Annulation Reaction of Cycl obutanones with Diynes and Enynes2008

    • Author(s)
      Shinji Ashida, Masahiro Murakami
    • Journal Title

      Bulletin of the Chemical Society of Japan 81

      Pages: 885-893

    • Related Report
      2007 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Rhodium-Catalyzed Carbonylation of Spiropentanes2007

    • Author(s)
      Takanori Matsuda, Tomoya Tsuboi, Masahiro Murakami
    • Journal Title

      J. Am. Chem. Soc. 129

      Pages: 12596-12597

    • Related Report
      2009 Final Research Report
    • Peer Reviewed
  • [Journal Article] Asymmetric Synthesis of 3, 4-Dihydrocoumarins by Rhodium-Catalyzed Reaction of 3-(2-Hydroxyphenyl)cyclobutanones2007

    • Author(s)
      Takanori Matsuda, Masanori Shigeno, Masahiro Murakami
    • Journal Title

      J. Am. Chem. Soc. 129

      Pages: 12086-12087

    • Related Report
      2009 Final Research Report
    • Peer Reviewed
  • [Journal Article] Rhodium-Catalyzed Carbonylation of Spiropentanes2007

    • Author(s)
      Takanori Matsuda, Tomoya Tsuboi, Masahiro Murakami
    • Journal Title

      Journal of the American Chemical Society 129

      Pages: 12596-12597

    • Related Report
      2007 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Asymmetric Synthesis of 3, 4-Dihydrocoumarins by Rhodium-Catalyzed Reaction of 3-(2-Hydroxyphenyl)cyclobutanones2007

    • Author(s)
      Takanori Matsuda, Masanori Shigeno, Masahiro Murakami
    • Journal Title

      Journal of the American Chemical Society 129

      Pages: 12086-12087

    • Related Report
      2007 Annual Research Report
    • Peer Reviewed
  • [Presentation] Enantioselective Carbon-Carbon Bond Cleavage: Rhodium-Catalyzed Restructuring of 3-Arylcyclobutanols into 1-Indanols2009

    • Author(s)
      Masahiro Murakami
    • Organizer
      Catalysis and Fine Chemicals 2009
    • Place of Presentation
      Korea University(韓国)
    • Year and Date
      2009-12-16
    • Related Report
      2009 Final Research Report
  • [Presentation] Enantioselective Carbon-Carbon Bond Cleavage : Rhodium-Catalyzed Restructuring of 3-Arylcyclobutanols into 1-Indanols2009

    • Author(s)
      Masahiro Murakami, Masanori Shigeno, Taiga Yamamoto
    • Organizer
      Catalysis and Fine Chemicals 2009
    • Place of Presentation
      Korea Univ.(韓国)
    • Year and Date
      2009-12-16
    • Related Report
      2009 Annual Research Report
  • [Presentation] Enantioselective Carbon-Carbon Bond Cleavage : Rhodium-Catalyzed Restructuring of 3-Arylcyclobutanols into 1-Indanols2009

    • Author(s)
      Masahiro Murakami, Masanori Shigeno, Taiga Yamamoto
    • Organizer
      The 4th International Conference on Cutting-Edge Organic Chemistry in Asia
    • Place of Presentation
      Chulabhorn Research Instithte(タイ)
    • Year and Date
      2009-12-02
    • Related Report
      2009 Annual Research Report
  • [Presentation] enantioselective synthesis of 1-indanols by rhodium-catalyzed activation of a carbon-carbon bond2009

    • Author(s)
      重野真徳, 山本泰河, 村上正浩
    • Organizer
      第56回有機金属化学討論会
    • Place of Presentation
      同志社大学(京都)
    • Year and Date
      2009-09-10
    • Related Report
      2009 Final Research Report
  • [Presentation] Rhodium-Catalyzed Asymmetric Synthesis of 3,4-Dihydrocoumarins via Enantioselective C-C Bond Cleavage of Cyclobutanones2009

    • Author(s)
      Masahiro Murakami, Masanori Shigeno, Takanori Matsuda
    • Organizer
      15^<th> IUPAC Symposium on Organometallic Chemistry directed towards Organic Synthesis
    • Place of Presentation
      グラスゴーロイヤルコンサートホール(UK)
    • Year and Date
      2009-07-29
    • Related Report
      2009 Annual Research Report
  • [Presentation] ロジウム触媒による3-アリールシクロブタノールから1-インダノールへのエナンチオ選択的異性化反応2009

    • Author(s)
      山本泰河, 重野真徳, 村上正浩
    • Organizer
      日本化学会第89春季年会(2009)
    • Place of Presentation
      日本大学(千葉)
    • Year and Date
      2009-03-27
    • Related Report
      2009 Final Research Report
  • [Presentation] Nickel-catalyzed Denitorogenative Alkyne Insertion of 1, 2, 3-Benzotriazin-4(3H)-ones2008

    • Author(s)
      Motoshi Yamauchi, Tomoya Miura, Masahiro Murakami
    • Organizer
      第55回有機金属化学論会
    • Place of Presentation
      大阪府立大学
    • Year and Date
      2008-09-29
    • Related Report
      2008 Annual Research Report
  • [Presentation] ロジウム触媒による炭素-炭素結合切断反応の合成化学的利用2008

    • Author(s)
      松田学則
    • Organizer
      日本化学会第88春季年会(2008)
    • Place of Presentation
      立教大学(東京)
    • Year and Date
      2008-03-27
    • Related Report
      2009 Final Research Report
  • [Presentation] ロジウム触媒による3-(2-ヒドロキシフェニル)シクロブタノンからの3, 4-ジヒドロクマリンの不斉合成2007

    • Author(s)
      ○重野真徳、松田学則、村上正浩
    • Organizer
      第54回有機金属化学討論会
    • Place of Presentation
      広島大学
    • Year and Date
      2007-10-27
    • Related Report
      2007 Annual Research Report
  • [Presentation] Rhodium-Catalyzed Asymmetric Synthesis of Lactones by Intramolecular Addition/Ring-Opening of Phenols to Cyclobutanones2007

    • Author(s)
      重野真徳, 松田学則, 村上正浩
    • Organizer
      第4回集積型合成国際シンポジウム(ISIS-4)
    • Place of Presentation
      滋賀
    • Year and Date
      2007-09-23
    • Related Report
      2009 Final Research Report
  • [Presentation] Synthesis of (+)-β-Cuparenone via Rhodium-Catalyzed Carbonylation fo Spiropentan2007

    • Author(s)
      ○Takanori, Matsuda, Tomoya Tsuboi, Masahiro Murakami
    • Organizer
      14th IUPAC Symposium on Organometallic Chemistry Directed Towards Organic Synthesis (OMCOS-14)
    • Place of Presentation
      奈良 100年会館
    • Year and Date
      2007-08-03
    • Related Report
      2007 Annual Research Report
  • [Presentation] Synthesis of (±)-β-Cuparenone via Rhodium-Catalyzed Carbonylation of Spiropentane2007

    • Author(s)
      Takanori Matsuda, Tomoya Tsuboi, Masahiro Murakami
    • Organizer
      14th IUPAC Symposium on Organometallic Chemistry Directed Towards Organic Synthesis (OMCOS14)
    • Place of Presentation
      奈良
    • Related Report
      2009 Final Research Report

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Published: 2007-04-01   Modified: 2016-04-21  

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