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Development of Iron-Catalyzed Cross-coupling Reactions by Controlling Coordination

Research Project

Project/Area Number 21750098
Research Category

Grant-in-Aid for Young Scientists (B)

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

Principal Investigator

HATAKEYAMA Takuji  Kyoto University, 化学研究所, 助教 (90432319)

Project Period (FY) 2009 – 2010
Project Status Completed (Fiscal Year 2010)
Budget Amount *help
¥4,550,000 (Direct Cost: ¥3,500,000、Indirect Cost: ¥1,050,000)
Fiscal Year 2010: ¥2,210,000 (Direct Cost: ¥1,700,000、Indirect Cost: ¥510,000)
Fiscal Year 2009: ¥2,340,000 (Direct Cost: ¥1,800,000、Indirect Cost: ¥540,000)
Keywords触媒・化学プロセス / クロスカップリン / 鉄触媒 / クロスカップリング
Research Abstract

Development of iron-catalyzed cross-coupling reactions have been intensively explored but not established well. We have developed biaryl cross-coupling using iron fluoride-NHC carbene catalyst and alkyl-aryl coupling using iron chloride-TMEDA catalyst with the aid of coordination control. In this project, we have carried out a series of mechanistic studies to reveal iron (II)-(III) and (II)-(IV) mechanism starting from aryliron (II) species. Based on these mechanisms, novel iron (II) chloride-phenylenediphosphine complexes have been synthesized, which enable us to develop iron-catalyzed Suzuki-Miyaura coupling reaction.

Report

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

    (28 results)

All 2011 2010 2009 Other

All Journal Article (14 results) (of which Peer Reviewed: 14 results) Presentation (9 results) Remarks (2 results) Patent(Industrial Property Rights) (3 results)

  • [Journal Article] Nickel-Catalyzed Alkenylative Cross-Coupling Reaction of Alkyl Sulfides2010

    • Author(s)
      Ishizuka, K. Seike, H. Hatakeyama, T. Nakamura, M.
    • Journal Title

      J.Am.Chem.Soc 132

      Pages: 13117-13119

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Iron-Catalyzed Suzuki-Miyaura Coupling of Alkyl Halides2010

    • Author(s)
      Hatakeyama, T. Hashimoto, T. Kondo, Y. Fujiwara, Y. Seike, H. Takaya, H. Tamada, Y. Ono, T. Nakamura, M.
    • Journal Title

      J.Am.Chem.Soc. 132

      Pages: 10674-10676

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Transition-Metal-Free Electrophilic Amination between Aryl Grignard Reagents and N-Chloroamines2010

    • Author(s)
      Hatakeyama, T. Yoshimoto, Y. Sujit, K.G. Nakamura, M.
    • Journal Title

      Org.Lett. 12

      Pages: 1516-1519

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Iron-Catalyzed Suzuki-Miyaura Coupling of Alkyl Halides2010

    • Author(s)
      Hatakeyama, T.; Hashimoto, T.; Kondo, Y.; Fujiwara, Y.;Seike, H.; Takaya, H.; Tamada, Y.; Ono, T.; Nakamura, M.
    • Journal Title

      J.Am.Chem.Soc.

      Volume: 132 Pages: 10674-10676

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Nickel-Catalyzed Alkenylative Cross-Coupling Reaction of Alkyl Sulfides2010

    • Author(s)
      Ishizuka, K.; Seike, H.; Hatakeyama, T.; Nakamura, M.
    • Journal Title

      J.Am.Chem.Soc.

      Volume: 132 Pages: 13117-13119

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Transition-Metal-Free Electrophilic Amination between Aryl Grignard Reagents and N-Chloroamines2010

    • Author(s)
      Hatakeyama, T.; Yoshimoto, Y.; Sujit, K.G.; Nakamura, M.
    • Journal Title

      Org.Lett.

      Volume: 132 Pages: 1516-1519

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Highly Selective Biaryl Cross-Coupling Reactions between Aryl Halides and Aryl Grignard Reagents: A New Catalyst Combination of N-Heterocyclic Carbenes and Iron, Cobalt, and Nickel Fluorides2009

    • Author(s)
      Hatakeyama, T. Hashimoto, S. Ishizuka, K. Nakamura, M.
    • Journal Title

      J.Am.Chem.Soc. 131

      Pages: 11949-11963

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Iron-Catalyzed Negishi Coupling Toward an Effective Olefin Synthesis2009

    • Author(s)
      Hatakeyama, T. Nakagawa, N. Nakamura, M.
    • Journal Title

      Org.Lett. 11

      Pages: 4496-4499

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Effect of TMEDA on Iron-catalyzed Coupling Reactions of ArylMgX with Alkyl Halides2009

    • Author(s)
      Noda, D. Sunada, Y. Hatakeyama, T. Nakamura, M. Nagashima, H.
    • Journal Title

      J.Am.Chem.Soc. 131

      Pages: 6078-6079

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Iron-Catalysed Fluoroaromatic Coupling Reactions under Catalytic Modulation with 1,2-Bis(diphenyl- phosphino)benzene2009

    • Author(s)
      Hatakeyama, T. Kondo, Y. Fujiwara, Y. Takaya, H. Ito, S. Nakamura, E. Nakamura, M.
    • Journal Title

      Chem.Comm.

      Pages: 1216-1218

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Iron-Catalysed Fluoroaromatic Coupling Reactions under Catalytic Modulation with 1,2-Bis(diphenylphosphino) benzene2009

    • Author(s)
      Hatakeyama, T.; Kondo, Y.; Fujiwara, Y.; Takaya, H.; Ito, S.; Nakamura, E.; Nakamura, M.
    • Journal Title

      Chem.Commun.

      Pages: 1216-1218

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Effect of TMEDA on Iron-catalyzed Coupling Reactions of ArylMgX with Alkyl Halides2009

    • Author(s)
      Noda, D.; Sunada, Y.; Hatakeyama, T.; Nakamura, M.; Nagashima, H.
    • Journal Title

      J.Am.Chem.Soc. 131

      Pages: 6078-6079

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Highly Selective Biaryl Cross-Coupling Reactions between Aryl Halides and Aryl Grignard Reagents : A New Catalyst Combination of N-Heterocyclic Carbenes and Iron, Cobalt, and Nickel Fluorides2009

    • Author(s)
      Hatakeyama, T.; Hashimoto, S.; Ishizuka, K.; Nakamura, M.
    • Journal Title

      J.Am.Chem.Soc. 131

      Pages: 11949-11963

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Iron-Catalyzed Negishi Coupling Toward an Effective Olefin Synthesis2009

    • Author(s)
      Hatakeyama, T.; Nakagawa, N.; Nakamura, M.
    • Journal Title

      Org.Lett. 11

      Pages: 4496-4499

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Presentation] 反応機構解析に立脚した鉄触媒クロスカップリング反応の精密制御2011

    • Organizer
      第1回熊本有機合成化学セミナー
    • Place of Presentation
      熊本
    • Year and Date
      2011-03-05
    • Related Report
      2010 Final Research Report
  • [Presentation] 反応機構解析に立脚した鉄触媒クロスカップリング反応の開発2011

    • Author(s)
      畠山琢次
    • Organizer
      第1回熊本有機合成化学セミナー
    • Place of Presentation
      熊本(招待講演)
    • Year and Date
      2011-03-05
    • Related Report
      2010 Annual Research Report
  • [Presentation] 鉄触媒クロスカップリング反応の開発と工業利用2011

    • Organizer
      SPring-8重点産業利用課題成果報告会
    • Place of Presentation
      東京
    • Year and Date
      2011-03-02
    • Related Report
      2010 Annual Research Report 2010 Final Research Report
  • [Presentation] 鉄触媒クロスカップリング反応の開発2010

    • Author(s)
      畠山琢次
    • Organizer
      新技術説明会
    • Place of Presentation
      大阪
    • Year and Date
      2010-12-09
    • Related Report
      2010 Annual Research Report
  • [Presentation] 鉄触媒クロスカップリング反応の開発と展望2010

    • Organizer
      関西TLO技術情報クラブ
    • Place of Presentation
      京都
    • Year and Date
      2010-12-01
    • Related Report
      2010 Final Research Report
  • [Presentation] 鉄触媒クロスカップリング反応の開発と展望2010

    • Author(s)
      畠山琢次
    • Organizer
      関西TLO技術情報クラブ
    • Place of Presentation
      京都(招待講演)
    • Year and Date
      2010-12-01
    • Related Report
      2010 Annual Research Report
  • [Presentation] 鉄触媒クロスカップリング反応の協奏制御2009

    • Organizer
      第104回触媒討論会「協奏機能触媒セッション」
    • Place of Presentation
      宮崎
    • Year and Date
      2009-09-30
    • Related Report
      2010 Final Research Report
  • [Presentation] 鉄触媒クロスカップリング反応の協奏制御2009

    • Author(s)
      畠山琢次
    • Organizer
      第104回触媒討論会
    • Place of Presentation
      宮崎
    • Year and Date
      2009-09-30
    • Related Report
      2009 Annual Research Report
  • [Presentation] 鉄族触媒ビアリールカップリングを用いた発光性π電子系化合物の開発2009

    • Organizer
      九州大学先導物質化学研究所「ユビキタス情報化社会を支える光利用有機・高分子化学」講演会
    • Place of Presentation
      福岡
    • Year and Date
      2009-09-24
    • Related Report
      2010 Final Research Report
  • [Remarks] ホームページ等

    • URL

      http://es.kuicr.kyoto-u.ac.jp/top.html

    • Related Report
      2010 Final Research Report
  • [Remarks]

    • URL

      http://es.kuicr.kyoto-u.ac.jp/

    • Related Report
      2010 Annual Research Report
  • [Patent(Industrial Property Rights)] アリールアミン類の製造方法2010

    • Inventor(s)
      中村正治・畠山琢次・曽我真一
    • Industrial Property Rights Holder
      京都大学・東ソー有機化学株式会社
    • Filing Date
      2010-11-15
    • Related Report
      2010 Final Research Report
  • [Patent(Industrial Property Rights)] クロスカップリング反応用触媒、及びこれを用いた芳香族化合物の製造方法2010

    • Inventor(s)
      中村正治・畠山琢次・藤原優一・
    • Industrial Property Rights Holder
      京都大学
    • Acquisition Date
      2010-01-07
    • Related Report
      2010 Final Research Report
  • [Patent(Industrial Property Rights)] アリールアミン類の製造方法2010

    • Inventor(s)
      中村正治・畠山琢次・曽我真一
    • Industrial Property Rights Holder
      京都大学・東ソー有機化学株式会社
    • Industrial Property Number
      2010-254603
    • Filing Date
      2010-11-15
    • Related Report
      2010 Annual Research Report

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Published: 2009-04-01   Modified: 2016-04-21  

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