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2013 Fiscal Year Final Research Report

Development and Control of Highly Efficient Catalytic Systems for Cross-and Multicomponent-Coupling Reactions

Research Project

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Project/Area Number 20225004
Research Category

Grant-in-Aid for Scientific Research (S)

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

Principal Investigator

KAMBE Nobuaki  大阪大学, 工学(系)研究科(研究院), 教授 (60144432)

Co-Investigator(Renkei-kenkyūsha) KUNIYASU Hitoshi  大阪大学, 大学院工学研究科, 准教授 (00252594)
IWASAKI Takanori  大阪大学, 大学院工学研究科, 助教 (50550125)
Project Period (FY) 2008-05-12 – 2013-03-31
Keywordsクロスカップリング / 多成分カップリング / 遷移金属触媒反応 / アート型錯体 / アルキル化 / グルニャール試薬 / ジエン
Research Abstract

A variety of methods for carbon-carbon bond formation have been developed by the aid of transition metal catalysts, which enabled introduction of congested secondary and tertiary alkyl groups into organic molecules, multi-component coupling incorporating unsaturated hydrocarbons such as alkynes and dienes, and cross coupling via cleavage of unreactive bonds such as C-F, C-O and C-H. These successful results demonstrated potent catalytic reactivities of anionic transition metal species as key intermediates in various synthetic reaction processes. Catalytic reactions for concomitant construct of carbon-carbon bonds and carbon-heteroatom bonds and those using electronically and/or structurally flexible metal complexes were also developed.

  • Research Products

    (11 results)

All 2014 2013 2012 2011 2010 2008 Other

All Journal Article (6 results) (of which Peer Reviewed: 6 results) Presentation (2 results) Book (1 results) Remarks (1 results) Patent(Industrial Property Rights) (1 results)

  • [Journal Article] Co-Catalyzed Cross-Coupling of Alkyl Halides with Tertiary Alkyl Grignard Reagents Using a 1,3-Butadiene Additive2013

    • Author(s)
      T.Iwasaki, H.Takagawa, S.P.Singh, H.Kuniyasu, N.Kambe
    • Journal Title

      J. Am. Chem. Soc.

      Volume: 135(26) Pages: 9604-9607

    • DOI

      10.1021/ja404285b

    • Peer Reviewed
  • [Journal Article] Rhodium-Catalyzed Intermolecular Oxidative Cross-Coupling of (Hetero)Arenes with Chalcogenophenes2013

    • Author(s)
      V.P.Reddy, R.Qiu, T.Iwasaki, N.Kambe
    • Journal Title

      Org. Lett.

      Volume: 15(6) Pages: 1290-1293

    • DOI

      10.1021/ol400230y

    • Peer Reviewed
  • [Journal Article] Copper-Catalyzed Coupling Reaction of Unactivated Secondary Alkyl Iodides with Alkyl Grignard Reagents in the Presence of 1,3-Butadiene as an Effective Additive2012

    • Author(s)
      R.Shen, T.Iwasaki, J.Terao, N.Kambe
    • Journal Title

      Chem. Commun.

      Volume: 48(47) Pages: 9313-9615

    • DOI

      10.1039/C2CC34847K

    • Peer Reviewed
  • [Journal Article] Silver-Catalyzed Regioselective Carbomagnesiation of Alkynes with Alkyl Halides and Grignard Reagents2011

    • Author(s)
      N.Kambe, Y.Moriwaki, Y.Fujii, T.Iwasaki, J.Terao
    • Journal Title

      Org. Lett.

      Volume: 13(17) Pages: 4656-4659

    • DOI

      10.1021/ol2018664

    • Peer Reviewed
  • [Journal Article] Nickel-Catalyzed Regioselective Carbomagnesation of Methylenecyclopropanes through a Site-Selective Carbon-Carbon Bond Cleavage2010

    • Author(s)
      J.Terao, M.Tomita, S.P.Singh, N.Kambe
    • Journal Title

      Angew. Chem. Int. Ed.

      Volume: 49(1) Pages: 144-147

    • DOI

      10.1002/anie.200904721

    • Peer Reviewed
  • [Journal Article] Platinum-Catalyzed Intramolecular Vinylchalcogenation of Alkynes with b-Phenylchalcogeno Conjugated Amides2008

    • Author(s)
      M.Toyofuku, S.-i.Fujiwara, T.Shin-ike, H.Kuniyasu, N.Kambe
    • Journal Title

      J. Am. Chem. Soc.

      Volume: 130(32) Pages: 10504-10505

    • DOI

      10.1021/ja804121j

    • Peer Reviewed
  • [Presentation] Transition Metal Catalyzed Alkylation Toward sp^<3->, sp^<2->, and sp-Carbons2011

    • Author(s)
      N.Kambe
    • Organizer
      International Symposium on Catalysis & Fine Chemicals 2011 (C&FC2011)
    • Place of Presentation
      奈良県
    • Year and Date
      2011-12-04
  • [Presentation] Alkyl Fluorides as Promising Alkylating Reagents2010

    • Author(s)
      N.Kambe
    • Organizer
      2010 International Chemical Congress of Pacific Basin Societies (Pacifichem 2010)
    • Place of Presentation
      米国、ハワイ
    • Year and Date
      2010-12-16
  • [Book] Coupling Reaction Between sp^<3->Carbon Centers, Comprehensive Organic Synthesis II (Second Edition) (P.Knochel, G.A.Molander Eds), Vol.32014

    • Author(s)
      T.Iwasaki, N.Kambe
    • Total Pages
      337-391
    • Publisher
      Elsevier
  • [Remarks]

    • URL

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

  • [Patent(Industrial Property Rights)] フルオレン誘導体の製造方法2013

    • Inventor(s)
      神戸宣明、寺尾 潤
    • Industrial Property Rights Holder
      ダイキン工業株式会社、国立大学法人大阪大学
    • Industrial Property Rights Type
      特許
    • Industrial Property Number
      特許第5283494号
    • Acquisition Date
      2013-06-07

URL: 

Published: 2015-07-16  

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