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

Research Project

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
Project Status Completed (Fiscal Year 2012)
Budget Amount *help
¥3,900,000 (Direct Cost: ¥3,000,000、Indirect Cost: ¥900,000)
Fiscal Year 2012: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
Fiscal Year 2011: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
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 / C-H活性化 / オリゴアセン類 / アリールボロン酸エステル
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.

Report

(3 results)
  • 2012 Annual Research Report   Final Research Report ( PDF )
  • 2011 Research-status Report
  • Research Products

    (52 results)

All 2013 2012 2011

All Journal Article (10 results) (of which Peer Reviewed: 10 results) Presentation (37 results) (of which Invited: 2 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

    • Related Report
      2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] Substituent Effects on Stoichiometric and Catalytic Cleavage of Carbon-Nitrogen Bonds in Aniline Derivatives by Ruthenium-Phosphine Complexes2013

    • Author(s)
      是枝徹郎、河内卓彌、垣内史敏
    • Journal Title

      Organometallics

      Volume: 32 Issue: 2 Pages: 682-690

    • DOI

      10.1021/om3011855

    • Related Report
      2012 Annual Research Report
    • 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

    • Related Report
      2012 Final Research Report
    • 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

    • Related Report
      2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] Short Synthesis of Alkyl-Substituted Acenes Using Carbonyl-Directed C-H and C-O Functionalization2012

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

      Org. Lett.

      Volume: 14 Issue: 15 Pages: 3882-3885

    • DOI

      10.1021/ol301608m

    • Related Report
      2012 Annual Research Report
    • 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 Issue: 17 Pages: 7718-7724

    • DOI

      10.1021/jo3012286

    • Related Report
      2012 Annual Research Report
    • 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

    • NAID

      10029522752

    • Related Report
      2012 Final Research Report
    • 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

    • Related Report
      2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] Ruthenium-Catalyzed Arylation of Fluorinated Aromatic Ketones via ortho-Selective Carbon-Fluorine Bond Cleavage2011

    • Author(s)
      河本圭介、河内卓彌、佐藤光央、水島英一郎、垣内史敏
    • Journal Title

      Tetrahedron Letters

      Volume: 52 Issue: 44 Pages: 5888-5890

    • DOI

      10.1016/j.tetlet.2011.09.005

    • Related Report
      2011 Research-status Report
    • Peer Reviewed
  • [Journal Article] Ruthenium-Catalyzed Acylation of Arylpyridines with Acyl Chlorides via ortho-Selective C-H Bond Cleavage2011

    • Author(s)
      河内卓彌、田澤葵、本田一起、垣内史敏
    • Journal Title

      Chemistry Letters

      Volume: 40 Issue: 9 Pages: 1018-1020

    • DOI

      10.1246/cl.2011.1018

    • NAID

      10029522752

    • Related Report
      2011 Research-status Report
    • 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
    • Related Report
      2012 Final Research Report
  • [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
    • Related Report
      2012 Final Research Report
  • [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
    • Related Report
      2012 Final Research Report
  • [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
    • Related Report
      2012 Final Research Report
  • [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
    • Related Report
      2012 Final Research Report
  • [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
    • Place of Presentation
      草津、滋賀
    • Related Report
      2012 Annual Research Report
    • Invited
  • [Presentation] 不活性炭素結合を利用するπ共役芳香族化合物の短工程合成2013

    • Author(s)
      垣内史敏
    • Organizer
      ァインケミカルズ合成触媒研究会セミナー
    • Place of Presentation
      東京
    • Related Report
      2012 Annual Research Report
  • [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)
      寺井誠弥、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
      草津、滋賀
    • Related Report
      2012 Annual Research Report
  • [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)
      小関裕太、河内卓彌、垣内史敏
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      草津、滋賀
    • Related Report
      2012 Annual Research Report
  • [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
      草津、滋賀
    • Related Report
      2012 Annual Research Report
  • [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
      草津、滋賀
    • Related Report
      2012 Annual Research Report
  • [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
    • Related Report
      2012 Annual Research Report 2012 Final Research Report
  • [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
    • Related Report
      2012 Annual Research Report 2012 Final Research Report
  • [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
    • Related Report
      2012 Final Research Report
  • [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
    • Related Report
      2012 Final Research Report
  • [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
    • Related Report
      2012 Final Research Report
  • [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
    • Related Report
      2012 Final Research Report
  • [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
    • Place of Presentation
      和光市、埼玉
    • Related Report
      2012 Annual Research Report
    • Invited
  • [Presentation] Mechanistic Studies of Aromatic C-H Bond Alkenylation Using Alkenyl Esters Catalyzed by Ru(cod)(cot)2012

    • Author(s)
      Yohei Ogiwara, Takuya Kochi, and Fumitoshi Kakiuchi
    • Organizer
      the Twelfth International Kyoto Conference on New Aspects of Organic Chemistry (IKCOC-12)
    • Place of Presentation
      京都
    • Related Report
      2012 Annual Research Report
  • [Presentation] Mechanistic Investigations of Ru(cod)(cot)-Catalyzed Alkenylation of Aromatic C–H Bonds Using Alkenyl Ester2012

    • Author(s)
      Yohei Ogiwara, Takuya Kochi, and Fumitoshi Kakiuchi
    • Organizer
      the XXV International Conference on Organometallic Chemistry (XXV ICOMC)
    • Place of Presentation
      Lisbon, Portugal
    • Related Report
      2012 Annual Research Report
  • [Presentation] 酸素脱離基を有するアルケン類を用いた芳香族炭素―水素結合の触媒的アルケニル化反応とその反応機構2012

    • Author(s)
      荻原陽平、河内卓彌、垣内史敏
    • Organizer
      第1回JACI/GSCシンポジウム
    • Place of Presentation
      東京
    • Related Report
      2012 Annual Research Report
  • [Presentation] Ru(cod)(cot)触媒によるアルケニルエステルを用いた芳香族化合物の位置選択的直接アルケニル化の反応機構に関する考察2012

    • Author(s)
      荻原陽平、河内卓彌、垣内史敏
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      慶應義塾大学日吉・矢上キャンパス
    • Related Report
      2011 Research-status Report
  • [Presentation] Development of New Procedures of Transition Metal-Catalyzed Carbon-Heteroatom Bond Formation2012

    • Author(s)
      垣内史敏
    • Organizer
      Paul Sabatier Lecture(招待講演)
    • Place of Presentation
      CNRS, Toulouse, France
    • Related Report
      2011 Research-status Report
  • [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(招待講演)
    • Place of Presentation
      Rennes 1 University, Rennes, France
    • Related Report
      2011 Research-status Report
  • [Presentation] Ruthenium-catalyzed Cross-couplings of Aromatic Ketones with Organoboronates via Unreactive Carbon-heteroatom Bonds Cleavage2012

    • Author(s)
      垣内史敏
    • Organizer
      Ecole Normale Supériere Lecture(招待講演)
    • Place of Presentation
      Ecole Normale Supériere de Paris, France
    • Related Report
      2011 Research-status Report
  • [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
    • Related Report
      2012 Final Research Report
  • [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
    • Related Report
      2012 Final Research Report
  • [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
    • Related Report
      2012 Final Research Report
  • [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
    • Related Report
      2012 Final Research Report
  • [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
    • Related Report
      2012 Final Research Report
  • [Presentation] Ruthenium-Catalyzed Arylation of sp3 C-O Bonds in Alkyl Ethers with Triarylboroxines via Dehydroalkoxylation2011

    • Author(s)
      荻原陽平、河内卓彌、垣内史敏
    • Organizer
      10th International Symposium of Organic Reactions
    • Place of Presentation
      慶應義塾大学矢上キャンパス
    • Related Report
      2011 Research-status Report
  • [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(招待講演)
    • Place of Presentation
      相模中研究所、綾瀬、神奈川
    • Related Report
      2011 Research-status Report
  • [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(招待講演)
    • Place of Presentation
      岡山市
    • Related Report
      2011 Research-status Report
  • [Presentation] Catalytic C-H Arylation of Aromatic Ketones with Arylboronates and Its Applications2011

    • Author(s)
      垣内史敏
    • Organizer
      14th Asian Chemical Congress(招待講演)
    • Place of Presentation
      Bangkok, Thailand
    • Related Report
      2011 Research-status Report
  • [Presentation] 第28回有機合成化学セミナー2011

    • Author(s)
      荻原陽平、田村賢、河内卓彌、垣内史敏
    • Organizer
      ルテニウム触媒による酸素脱離基を有するアルケン類を用いた芳香族化合物の位置選択的直接官能基化反応とその反応機構
    • Place of Presentation
      天童市
    • Related Report
      2011 Research-status Report
  • [Presentation] Ruthenium-Catalyzed C-C Bond Formation at sp3 C-O Bonds in EthersUsing Arylboroxines2011

    • Author(s)
      荻原陽平、河内卓彌、垣内史敏
    • Organizer
      16th Organometallic Chemistry towards Organic Synthesis
    • Place of Presentation
      上海、中国
    • Related Report
      2011 Research-status Report
  • [Presentation] Short-step Syntheses of Multi-substituted Acenes by Combination of C-H Functionalization and Transformation of Carbonyl Groups2011

    • Author(s)
      北澤謙太郎、松村大植、河内卓彌、垣内史敏
    • Organizer
      16th Organometallic Chemistry towards Organic Synthesis
    • Place of Presentation
      上海、中国
    • Related Report
      2011 Research-status Report
  • [Book] C-H結合活性化反応2011

    • Author(s)
      垣内史敏
    • Publisher
      ネヌ・ティー・エス
    • Related Report
      2012 Final Research Report
  • [Book] sp^2 炭素-水素結合のアルキル化2011

    • Author(s)
      垣内史敏
    • Publisher
      化学同人
    • Related Report
      2012 Final Research Report
  • [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
    • Publisher
      化学同人
    • Related Report
      2012 Final Research Report
  • [Book] 新展開を見せるC-H活性化研究2011

    • Author(s)
      垣内史敏
    • Publisher
      化学同人
    • Related Report
      2012 Final Research Report
  • [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
    • Publisher
      Ohm Bulletin
    • Related Report
      2012 Final Research Report

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Published: 2011-08-05   Modified: 2019-07-29  

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