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2012 Fiscal Year Final Research Report

Development of Novel Synthetic Methods of Soluble Graphene Derivatives Having Transistor Performance

Research Project

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Project/Area Number 23655090
Research Category

Grant-in-Aid for Challenging Exploratory Research

Allocation TypeMulti-year Fund
Research Field Synthetic chemistry
Research InstitutionKeio University

Principal Investigator

KAKIUCHI Fumitoshi  慶應義塾大学, 理工学部, 教授 (70252591)

Project Period (FY) 2011 – 2012
KeywordsC-H活性化 / 有機トランジスタ / アリール化 / グラフェン類 / オリゴアセン類アリールボロン酸エステル / 芳香族ケトン / 遷移金属錯体触媒
Research Abstract

We have studied development of short syntheses of polycyclic aromatic hydrocarbons using coupling of aromatic ketones and arylboronates via carbon-hydrogen, carbon-oxygen, and carbon-nitrogen bond cleavages and have examined applications of these polycycl
1) development of multi-arylation of acetophenones via unreactive carbon bond cleavage and construction of benzene ring by transformation of acetyl groups;
2) development of new methods of short synthesis of polycyclic aromatic hydrocarbons having graphene frameworks by our multi-arylation protocols;
3) measurements of OFET performance of the synthesized polycyclic aromatic hydrocarbons.

  • Research Products

    (26 results)

All 2013 2012 2011

All Journal Article (5 results) (of which Peer Reviewed: 5 results) Presentation (16 results) Book (5 results)

  • [Journal Article] Substituent Effects on Stoichiometoric and Catalytic Cleavage of Carbon-Nitrogen Bonds in Aniline Derivatives by Ruthenium-Phosphine Complexes2013

    • Author(s)
      T. Koreeda, T. Kochi, F. Kakiuchi
    • Journal Title

      Organometallics

      Volume: 32(2) Pages: 682-690

    • Peer Reviewed
  • [Journal Article] Catalytic Electrochemical C-H Iodination and One-Pot Arylation by ON/OFF Switching of Electric Current2012

    • Author(s)
      H. Aiso, T. Kochi, H. Mutsutani, T. Tanabe, S. Nishiyama, F. Kakiuchi
    • Journal Title

      J. Org. Chem.

      Volume: 77(17) Pages: 7718-7724

    • Peer Reviewed
  • [Journal Article] Short Synthesis of Alkyl-Substituted Acenes Using Carbonyl-Directed C-H and C-O Functionalization2012

    • Author(s)
      D. Matsuura, K. Kitazawa, S. Terai, T. Kochi, Y. Ie, M. Nitani, Y. Aso, F. Kakiuchi
    • Journal Title

      Org. Lett.

      Volume: 14(15) Pages: 3882-3885

    • Peer Reviewed
  • [Journal Article] Ruthenium-Catalyzed Acylation of Arylpyridines with Acyl Chlorides via ortho-Selective C-H Bond Cleavage2011

    • Author(s)
      T. Kochi, A. Tazawa, K. Honda, and F. Kakiuchi
    • Journal Title

      Chem. Lett.

      Volume: 40(9) Pages: 1018-1020

    • Peer Reviewed
  • [Journal Article] Ruthenium-Catalyzed Arylation of Fluorinated Aromatic Ketones via ortho-Selective Carbon-Fluorine Bond Cleavage2011

    • Author(s)
      K. Kawamoto, T. Kochi, M. Sato, E. Mizushima, F. Kakiuchi
    • Journal Title

      Tetrahedron Lett.

      Volume: 52(44) Pages: 5888-5890

    • Peer Reviewed
  • [Presentation] Catalytic Arylations of Aromatic Compounds via Unreactive Bond Cleavage and Its Applications2013

    • Author(s)
      垣内史敏
    • Organizer
      日加国際交流シンポジウム: 次世代の遷移金属触媒・合成反応プロセス
    • Place of Presentation
      立命館大学びわこ・くさつキャンパス、草津、滋賀
    • Year and Date
      2013-03-23
  • [Presentation] ルテニウム触媒によるo-アシルアニリン類の炭素-窒素結合切断を経る脱アミノ化反応およびアルキル化反応2013

    • Author(s)
      是枝徹郎、河内卓彌、垣内史敏
    • Organizer
      日本化学会第93 春季年会
    • Place of Presentation
      立命館大学びわこ・くさつキャンパス、草津、滋賀
    • Year and Date
      2013-03-23
  • [Presentation] アリールボロン酸エステルを用いたルテニウム触媒による炭素-水素結合切断を経る芳香族ニトリルのアリール化反応2013

    • Author(s)
      小関祐太、河内卓彌、垣内史敏
    • Organizer
      日本化学会第93 春季年会
    • Place of Presentation
      立命館大学びわこ・くさつキャンパス、草津、滋賀
    • Year and Date
      2013-03-23
  • [Presentation] 芳香族炭素-水素結合および炭素-酸素結合の触媒的アリール化反応を用いたテトラベンゾコロネン誘導体の効率的合成2013

    • Author(s)
      寺井誠也、北澤謙太郎、河内卓彌、垣内史敏
    • Organizer
      日本化学会第93 春季年会
    • Place of Presentation
      立命館大学びわこ・くさつキャンパス、草津、滋賀
    • Year and Date
      2013-03-23
  • [Presentation] ルテニウム触媒による炭素-酸素または窒素結合の選択的切断を経る芳香族ケトンのモノアルケニル化反応2013

    • Author(s)
      秋葉奈々、河内卓彌、垣内史敏
    • Organizer
      日本化学会第93 春季年会
    • Place of Presentation
      立命館大学びわこ・くさつキャンパス、草津、滋賀
    • Year and Date
      2013-03-23
  • [Presentation] ルテニウム触媒を用いたアリールボロン酸エステルによる芳香族ニトリルの位置選択的アリール化反応2012

    • Author(s)
      小関祐太、河内卓彌、垣内史敏
    • Organizer
      第59回有機金属化学討論会
    • Place of Presentation
      吹田、大阪
    • Year and Date
      2012-09-14
  • [Presentation] ルテニウム触媒を用いたアリールピリジン類とアルケニルエステルのカップリング反応に関する反応機構の考察2012

    • Author(s)
      荻原陽平、河内卓彌、垣内史敏
    • Organizer
      第59回有機金属化学討論会
    • Place of Presentation
      吹田、大阪
    • Year and Date
      2012-09-14
  • [Presentation] Mechanistic Investigations of Ru(cod)(cot)-Catalyzed Alkenylation of Aromatic C-H Bonds Using Alkenyl Ester2012

    • Author(s)
      荻原陽平、河内卓彌、垣内史敏
    • Organizer
      the XXV International Conference on Organometallic Chemistry (XXV ICOMC)
    • Place of Presentation
      Lisbon, Protugal
    • Year and Date
      2012-09-04
  • [Presentation] 不活性炭素-ヘテロ原子結合を利用した合成反応の開発2012

    • Author(s)
      垣内史敏
    • Organizer
      理研シンポジウム 第7回有機合成化学のフロンティア
    • Place of Presentation
      理化学研究所、和光、埼玉
    • Year and Date
      2012-07-06
  • [Presentation] Catalytic C-H Functionalization of Aromatic Ketones and Its Applications2012

    • Author(s)
      垣内史敏
    • Organizer
      International Green Catalysis Symposium: Advanced Spring School on Green Catalysis
    • Place of Presentation
      Rennes 1 University, Rennes, France
    • Year and Date
      2012-03-09
  • [Presentation] Ruthenium-catalyzed Cross-couplings of Aromatic Ketones with Organoboronates via Unreactive Carbon-heteroatom Bonds Cleavage2012

    • Author(s)
      垣内史敏
    • Organizer
      Faculty Lecture at Ecole Normal de Paris
    • Place of Presentation
      Paris, France
    • Year and Date
      2012-03-05
  • [Presentation] Ruthenium-Catalyzed Arylation of sp3C-H Bonds in Alkyl Ethers with Triarylboroxines via Dehydroalkoxylation2011

    • Author(s)
      垣内史敏
    • Organizer
      10th Internal Symposium of Organic Reactions
    • Place of Presentation
      横浜、神奈川
    • Year and Date
      2011-11-23
  • [Presentation] 不活性炭素結合を利用した触媒反応の開発と利用2011

    • Author(s)
      垣内史敏
    • Organizer
      第8回触媒相模セミナー
    • Place of Presentation
      綾瀬、神奈川
    • Year and Date
      2011-11-17
  • [Presentation] 炭素-水素結合を利用した触媒的官能基導入法の開発2011

    • Author(s)
      垣内史敏
    • Organizer
      Green Chemistry Forum
    • Place of Presentation
      Okayama, Okayama
    • Year and Date
      2011-10-31
  • [Presentation] Catalytic C-H Arylation of Aromatic Ketones with Arylboronates and Its Applications2011

    • Author(s)
      垣内史敏
    • Organizer
      14th Asian Chemical Congress
    • Place of Presentation
      Bangkok, Thailand
    • Year and Date
      2011-09-06
  • [Presentation] 不活性炭素-水素結合切断を経る触媒的官能基導入法の開発と利用2011

    • Author(s)
      垣内史敏
    • Organizer
      第28回有機合成化学セミナー
    • Place of Presentation
      山形県天童市
    • Year and Date
      2011-08-31
  • [Book] C-H結合活性化反応2011

    • Author(s)
      垣内史敏
    • Total Pages
      375-381
    • Publisher
      ネヌ・ティー・エス
  • [Book] sp^2 炭素-水素結合のアルキル化2011

    • Author(s)
      垣内史敏
    • Total Pages
      40-49
    • Publisher
      化学同人
  • [Book] C-H活性化研究の流れ,研究の歴史2011

    • Author(s)
      茶谷直人、垣内史敏
    • Total Pages
      10-19
    • Publisher
      化学同人
  • [Book] 新展開を見せるC-H活性化研究2011

    • Author(s)
      垣内史敏
    • Total Pages
      24-29
    • Publisher
      化学同人
  • [Book] クロスカップリングで何がどう変わる2011

    • Author(s)
      垣内史敏
    • Total Pages
      2-4
    • Publisher
      Ohm Bulletin

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Published: 2014-08-29   Modified: 2014-10-02  

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