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

2008 Fiscal Year Final Research Report

Innovative Advanced Protocols for Constructing Carbon-Carbon Bonds via Activation of Aromatic Carbon-Hydrogen Bond

Research Project

  • PDF
Project/Area Number 17065016
Research Category

Grant-in-Aid for Scientific Research on Priority Areas

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

Principal Investigator

KAKIUCHI Fumitoshi  Keio University, 理工学部, 教授 (70252591)

Project Period (FY) 2005 – 2008
Keywordsルテニウム錯体触媒 / 芳香族化合物 / 芳香族炭素-水素結合切断 / 炭素-炭素結合生成 / 酸クロライド類 / 不活性結合切断 / ヘテロ芳香族化合物 / 有機ホウ素化号物
Research Abstract

Innovative Advanced Protocols 本研究では,遷移金属触媒を用いた芳香族炭素-水素結合切断を経る炭素-炭素結合生成を伴う反応の機構の解明と新規カップルリング反応の開発を行った。その結果、アルケニルエステルを用いたアルケニル化反応、アリール典型金属化合物とのカップリング反応、エステル基やアミド基等の極性官能基の導入反応、アセンキノン類を多置換アセン類へ短工程で変換する新手法など、既存の方法では合成が困難であった化合物を簡便に合成できる手法の開発に成功した。

  • Research Products

    (24 results)

All 2009 2008 2007 2006 2005

All Journal Article (11 results) (of which Peer Reviewed: 11 results) Presentation (7 results) Book (1 results) Patent(Industrial Property Rights) (5 results) (of which Overseas: 2 results)

  • [Journal Article] Cleavage of C-N Bonds in Aniline Derivatives on a Ruthenium Center and Its Relevance to Catalytic C-C Bond Formation2009

    • Author(s)
      Tetsuro Koreeda, Takuya Kochi, and Fumitoshi Kakiuchi
    • Journal Title

      J. Am. Chem. Soc., 131

      Pages: 7238-7239

    • Peer Reviewed
  • [Journal Article] Convenient Synthesis of Tetra- and Hexaarylanthracenes by Means of RuH2(CO)(PPh3)3-Catalyzed C-H Arylation of Anthraquinone with Arylboronates;2009

    • Author(s)
      Kentaroh Kitazawa, Takuya Kochi, Mitsuo Sato, and Fumitoshi Kakiuchi
    • Journal Title

      Org. Lett 11(9)

      Pages: 951-954

    • Peer Reviewed
  • [Journal Article] Ruthenium-Catalyzed Amino-and Alkoxycarbonylations with Carbamoyl Chlorides and Alkyl Chloroformates via Aromatic C-H Bond Cleavage;2009

    • Author(s)
      Takuya Kochi, Seiya Urano, Hajime Seki, Eiichiro Mizushima, Mitsuo Sato, and Fumitoshi, Kakiuchi
    • Journal Title

      J. Am. Chem. Soc. 131(8)

      Pages: 2792-2793

    • Peer Reviewed
  • [Journal Article] Unique Effect of Coordination of an Alkene Moiety in Products on Ruthenium-Catalyzed Chemoselective C-H Alkenylation;2009

    • Author(s)
      Satoshi Ueno, Takuya Kochi, Naoto Chatani, and Fumitoshi Kakiuchi
    • Journal Title

      Org. Lett., 11(4)

      Pages: 855-858

    • Peer Reviewed
  • [Journal Article] Transition Metal-Catalyzed Carbon-Carbon Bond Formation via Carbon-Hydrogen Bond Cleavage2008

    • Author(s)
      Fumitoshi Kakiuchi and Takuya Kochi
    • Journal Title

      Synthesis (10)

      Pages: 3013-3039

    • Peer Reviewed
  • [Journal Article] The Ru(cod)(cot)-Catalyzed Alkenylation of Aromatic C-H Bonds with Alkenyl Acetates;2007

    • Author(s)
      Yusuke Matsuura, Masaru Tamura, Takuya Kochi, Mitsuo Sato, Naoto Chatani, and Fumitoshi Kakiuchi,
    • Journal Title

      J. Am. Chem. Soc., 129(32)

      Pages: 9858-9859

    • Peer Reviewed
  • [Journal Article] Ruthenium-Catalyzed Carbon-Carbon Bond Formation via the Cleavage of an Unreactive Aryl Carbon-Nitrogen Bond in Aniline Derivatives with Organoboronates2007

    • Author(s)
      Satoshi Ueno, Naoto Chatani, and Fumitoshi Kakiuchi
    • Journal Title

      J. Am. Chem. Soc., 129(19)

      Pages: 6098-6099

    • Peer Reviewed
  • [Journal Article] Regioselective Alkenylation of Aromatic Ketones with Alkenylboronates Using a RuH2(CO)(PPh3)3-Catalyst via Carbon-Hydrogen Bond Cleavage Regioselective2007

    • Author(s)
      Satoshi Ueno, Naoto Chatani, and Fumitoshi Kakiuchi
    • Journal Title

      J. Org. Chem 72(9)

      Pages: 3600-3602

    • Peer Reviewed
  • [Journal Article] Ru/C-Catalyzed Carbonylation at ortho-C-H Bonds in 2-Phenylpyridines2007

    • Author(s)
      Shinya Imoto, Takeshi Uemura, Fumitoshi Kakiuchi, and; Naoto Chatani
    • Journal Title

      Synlett

      Pages: 170-172

    • Peer Reviewed
  • [Journal Article] Direct Observation of the Oxidative Addition of the Aryl Carbon-Oxygen Bond to a Ruthenium Complex and Consideration of the Relative Reactivity between Aryl Carbon-Oxygen and Aryl Carbon-Hydrogen Bonds2006

    • Author(s)
      Satoshi Ueno, Eiichiro Mizushima, Naoto Chatani, and Fumitoshi Kakiuchi
    • Journal Title

      J. Am. Chem. Soc., 128(51)

      Pages: 16516-16517

    • Peer Reviewed
  • [Journal Article] Synthesis of [Ru(CO)2 (PPh3)(SP)] and Ru(CO)(PPh3)2(SP)] and Their CatalyticActivities for the Hydroamination of Phenylacetylene2006

    • Author(s)
      Eiichiro Mizushima, Naoto Chatani, and Fumitoshi Kakiuchi,
    • Journal Title

      J. Organomet. Chem., 691(26)

      Pages: 5739-5745

    • Peer Reviewed
  • [Presentation] 炭素-水素結合を利用した炭素官能基導入の新手法2009

    • Author(s)
      垣内史敏
    • Organizer
      第57回有機合成化学協会関東支部シンポジウム
    • Place of Presentation
      早稲田大学、東京
    • Year and Date
      2009-05-09
  • [Presentation] RuCl2(PPh3)3-Catalyzed Chelation-Assisted Alkoxy-and Aminocarbonylation of Aromatic C-H Bond2008

    • Author(s)
      垣内史敏
    • Organizer
      The 9th International Symposium on Organic Reactions
    • Place of Presentation
      Nice Plaza Hotel, Taiwan
    • Year and Date
      2008-11-22
  • [Presentation] Ruthenium-Catalyzed Cross-Coupling Reactions of Aromatic Ketones with Organoboronates via Aryl Carbon-Oxygen and-Nitrogen Bonds Cleavage2008

    • Author(s)
      垣内史敏
    • Organizer
      The 9th International Symposium on Organic Reactions Pre-Symposium
    • Place of Presentation
      National Taiwan Normal University, Taiwan
    • Year and Date
      2008-11-19
  • [Presentation] A New Strategy for Synthesis of π-Conjugated Aromatic Compounds via C-H Bond Cleavage2008

    • Author(s)
      垣内史敏
    • Organizer
      Japan-Korea Joint Symposium on Functional Materials toward Future Catalysts: Chemistry Showcase
    • Place of Presentation
      Korea Advanced Institute Scienceand Technology, Korea
    • Year and Date
      2008-11-04
  • [Presentation] Ruthenium-Catalyzed Alkenylation of Aromatic C-H Bonds with Alkenyl Acetates2008

    • Author(s)
      垣内史敏、田村賢、河内卓彌
    • Organizer
      23rd International Conference on Organometallic Chemistry
    • Place of Presentation
      Rennes 1 University, France
    • Year and Date
      2008-07-15
  • [Presentation] Ruthenium-Catalyzed Coupling Reaction of Aromatic Ketones with Compounds2005

    • Author(s)
      垣内史敏
    • Organizer
      PACIFICHEM2005 (2005 環太平洋国際化学会議)
    • Place of Presentation
      Waikiki, Hawaii
    • Year and Date
      2005-12-17
  • [Presentation] Ruthenium-Catalyzed Coupling of Aromatic Compounds with Organoboronates via Carbon-Hydrogen Bond Cleavage2005

    • Author(s)
      垣内史敏
    • Organizer
      Pre OMCOS 13
    • Place of Presentation
      Paris, France
    • Year and Date
      2005-07-15
  • [Book] Topics in Organometallic Chemistry: Directed Metallation: "Catalytic Addition of C-H Bonds to C-C Multiple Bonds"2007

    • Author(s)
      Fumitoshi Kakiuchi
    • Total Pages
      pp 1-33
    • Publisher
      Springer: Berlin
  • [Patent(Industrial Property Rights)] 芳香族化合物及びその製造方法2009

    • Inventor(s)
      垣内史敏、寺井宏樹
    • Industrial Property Rights Holder
      学校法人慶應義塾、住友化学株式会社
    • Industrial Property Number
      特願2009-109577
    • Filing Date
      2009-04-28
  • [Patent(Industrial Property Rights)] 電気分解を利用した芳香族ハロゲン化合物の製造方法2009

    • Inventor(s)
      垣内史敏
    • Industrial Property Rights Holder
      学校法人慶應義塾
    • Industrial Property Number
      特願2009-056402
    • Filing Date
      2009-03-10
  • [Patent(Industrial Property Rights)] 芳香族化合物の製造方法2009

    • Inventor(s)
      垣内史敏、寺井宏樹
    • Industrial Property Rights Holder
      学校法人慶應義塾、住友化学株式会社
    • Industrial Property Number
      特願2009-021271
    • Filing Date
      2009-02-02
  • [Patent(Industrial Property Rights)] 芳香族カルボニル化合物の製造方法2009

    • Inventor(s)
      垣内史敏、小熊潤
    • Industrial Property Rights Holder
      学校法人慶應義塾、住友化学株式会社
    • Industrial Property Number
      TW0001396
    • Filing Date
      2009-01-25
    • Overseas
  • [Patent(Industrial Property Rights)] 三置換芳香族化合物2009

    • Inventor(s)
      垣内史敏、寺井宏樹
    • Industrial Property Rights Holder
      学校法人慶應義塾、住友化学株式会社
    • Industrial Property Number
      PCT/JP2009/050531;特願2008-014915
    • Filing Date
      2009-02-02
    • Overseas

URL: 

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

Information User Guide FAQ News Terms of Use Attribution of KAKENHI

Powered by NII kakenhi