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2013 Fiscal Year Final Research Report

Hydrogen Transfer Carbon-Carbon Bond Forming Reaction via Hetero-Nickelacycles

Research Project

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Project/Area Number 21245028
Research Category

Grant-in-Aid for Scientific Research (A)

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

Principal Investigator

OGOSHI SENSUKE  大阪大学, 工学(系)研究科(研究院), 教授 (30252589)

Co-Investigator(Renkei-kenkyūsha) OHSHI Masato  大阪大学, 大学院工学研究科, 講師 (60397635)
HOSHIMOTO Yoichi  大阪大学, 大学院工学研究科, 助教 (30710074)
Project Period (FY) 2009-04-01 – 2013-03-31
Keywordsニッケル / 酸化的環化 / 水素移動 / 炭素-炭素結合形成
Research Abstract

The reaction of two different unsaturated compounds with Ni(0) species can give an acyclic organic compounds by formation of nickelacycles followed by beta-hydrogen elimination and reductive elimination. This reaction can be applied to the dimerization of aldehyde to give esters. Moreover, the selective crossed-dimerization of two different aldehydes to give one ester was also achieved.

  • Research Products

    (22 results)

All 2014 2012 2011 2010 2009 Other

All Journal Article (11 results) Presentation (10 results) Remarks (1 results)

  • [Journal Article] One-Pot, Single-Step and Gram-Scale Synthesis of Mononuclear [(η6-arene)Ni(N-heterocyclic Carbene)] Complexes; Useful Precursors of the Ni(0)-NHC Unit2014

    • Author(s)
      Y. Hoshimoto, Y. Hayashi, H. Suzuki, M. Ohashi, S. Ogoshi
    • Journal Title

      Organometallics

      Volume: 33 Pages: 1276-1282

  • [Journal Article] Nickel-Catalyzed Synthesis of N-Aryl-1,2-Dihydropyridines by [2+2+2] Cycloaddition of Imines with Alkynes through T-Shaped 14-Electron Aza-Nickelacycle Key Intermediates2014

    • Author(s)
      Y. Hoshimoto, T. Ohata, M. Ohashi, S. Ogoshi
    • Journal Title

      Chem. Eur. J

      Volume: 20 Pages: 4105-4110

  • [Journal Article] Synthesis of Five- and Six-Membered Benzocyclic Ketones through Intramolecular Alkene Hydroacylation Catalyzed by Nickel(0)/N-Heterocyclic Carbenes2012

    • Author(s)
      Y. Hoshimoto, Y. Hayashi, H. Suzuki, M. Ohashi, S. Ogoshi
    • Journal Title

      Angew. Chem. Int. Ed

      Volume: 51 Pages: 10812-10815

  • [Journal Article] Nickel-Catalyzed Intermolecular [2 + 2] Cycloaddition of Conjugated Enynes with Alkenes2012

    • Author(s)
      A, Nishimura, M. Ohashi, S. Ogoshi
    • Journal Title

      J. Am. Chem. Soc

      Volume: 134 Pages: 15692-15695

  • [Journal Article] Nickel-catalyzed Dehydrogenative [4 + 2] Cycloaddition of 1,3-Dienes with Nitriles2011

    • Author(s)
      M. Ohashi, I. Takeda, M. Ikawa, S. Ogoshi
    • Journal Title

      J. Am. Chem. Soc

      Volume: 133 Pages: 18018-18021

  • [Journal Article] [3+2] Cycloaddition Reaction of Cyclopropyl Ketones with Alkynes Catalyzed by Nickel/Me2AlCl2011

    • Author(s)
      T. Tamaki, M. Ohashi, S. Ogoshi
    • Journal Title

      Angew. Chem. Int. Ed

      Volume: 50 Pages: 12067-12070

  • [Journal Article] Nickel-Catalyzed Formation of Cyclopentenone Derivatives via the Unique Cycloaddition of α,β-Unsaturated Phenyl Esters with Alkynes2011

    • Author(s)
      M. Ohashi, T. Taniguchi, S. Ogoshi
    • Journal Title

      J. Am. Chem. Soc

      Volume: 133 Pages: 14900-14903

  • [Journal Article] Nickel-Catalyzed Selective Conversion of Two Different Aldehydes to Cross-Coupled Esters2011

    • Author(s)
      Y. Hoshimoto, M. Ohashi, S. Ogoshi
    • Journal Title

      J. Am. Chem. Soc

      Volume: 133 Pages: 4668-4671

  • [Journal Article] Palladium-catalyzed coupling reactions of tetrafluoroethylene with arylzinc compounds2011

    • Author(s)
      M. Ohashi, T. Kambara, T. Hatanaka, H. Saijo, R. Doi, S. Ogoshi
    • Journal Title

      J. Am. Chem. Soc

      Volume: 133 Pages: 3256-3259

  • [Journal Article] Nickel-Catalyzed Direct Conjugate Addition of Simple Alkenes to Enones2009

    • Author(s)
      S. Ogoshi, T. Haba, M. Ohashi
    • Journal Title

      J. Am. Chem. Soc

      Volume: 131 Pages: 10350-10351

  • [Journal Article] Ni(0)-Catalyzed Formation of Azaaluminacyclopentenes via Azanickelacyclopentenes : A Unique Nickel/Aluminum Double Transmetalation Reaction2009

    • Author(s)
      M. Ohashi, O. Kishizaki, H. Ikeda, S. Ogoshi
    • Journal Title

      J. Am. Chem. Soc

      Volume: 131 Pages: 9160-9161

  • [Presentation] Nickel-Catalyzed Reactions of α,β-Unsaturated Compouds with Alkynes and Alkenes: Selective Synthesis of Cyclic and Acyclic Compounds2012

    • Author(s)
      Ogoshi, Sensuke
    • Organizer
      17th Malaysian Chemical Congress
    • Place of Presentation
      Kuala Lumpur, Malaysia
    • Year and Date
      20121015-17
  • [Presentation] パラジウム触媒を用いるパーフルオロアルケン類の変換反応2012

    • Author(s)
      生越専介
    • Organizer
      第9回触媒相模セミナー
    • Place of Presentation
      東ソー東京センター
    • Year and Date
      2012-11-15
  • [Presentation] 環状ニッケル化合物を反応中間体とする触媒反応開発2012

    • Author(s)
      生越専介
    • Organizer
      第102回有機合成シンポジウム
    • Place of Presentation
      早稲田大学国際会議場
    • Year and Date
      2012-11-09
  • [Presentation] パーフルオロアルケン類の有用フッ素化合物への変換反応2012

    • Author(s)
      生越専介
    • Organizer
      第24回万有札幌シンポジウム
    • Place of Presentation
      北海道大学
    • Year and Date
      2012-07-07
  • [Presentation] Palladium-catalyzed Coupling Reaction of Tetrafluoroethylene with Ar2Zn2011

    • Author(s)
      Ogoshi, Sensuke
    • Organizer
      10th International Symposium on Organic Reactions
    • Place of Presentation
      横浜
    • Year and Date
      20111121-24
  • [Presentation] テトラフルオロエチレンの触媒的変換反応2011

    • Author(s)
      生越専介
    • Organizer
      第35回フッ素化学討論会
    • Place of Presentation
      岡山
    • Year and Date
      20110926-27
  • [Presentation] Nickel-catalyzed selective crossed dimerization of two different aldehydes2011

    • Author(s)
      Ogoshi, Sensuke
    • Organizer
      4th Asian Chemical Congress
    • Place of Presentation
      Bangkok, Thailand
    • Year and Date
      20110905-08
  • [Presentation] Dehydrogenative [4+2] Cycloaddition of 1,3-Dienes with Nitriles Catalyzed by Nickel(0) Complexes2011

    • Author(s)
      Ogoshi, Sensuke
    • Organizer
      International Symposium on OrganoMetallic Chemistry 2011
    • Place of Presentation
      大阪大学
    • Year and Date
      2011-11-12
  • [Presentation] [2+2+2]Cycloaddition of Two Enones and An Alkyne via Oxidative Cyclization of An Alkyne and An Enone with A Nickel(0) Complex2010

    • Author(s)
      Ogoshi, Sensuke
    • Organizer
      24^<th> International Conference on Organometallic Chemistry (ICOMC 2010)
    • Place of Presentation
      台北(台湾)
    • Year and Date
      2010-07-21
  • [Presentation] ニッケル触媒による単純アルケンのエノンへの直接共役付加2009

    • Author(s)
      生越専介
    • Organizer
      第56回有機金属化学討論会
    • Place of Presentation
      京都
    • Year and Date
      2009-09-09
  • [Remarks]

    • URL

      http://www.chem.eng.osaka-u.ac.jp/~kuroken/index.html

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Published: 2015-07-16  

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