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Synlett 2002(7): 1137-1139
DOI: 10.1055/s-2002-32608
LETTER
© Georg Thieme Verlag Stuttgart · New York

Palladium-Catalyzed Coupling Reaction of Alkenylgalliums with Aryl Halides

Satoshi Mikami, Hideki Yorimitsu, Koichiro Oshima*
Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Yoshida, Sakyo-ku, Kyoto 606-8501, Japan
Fax: +81(75)7534863; e-Mail: oshima@fm1.kuic.kyoto-u.ac.jp;
Further Information

Publication History

Received 16 February 2002
Publication Date:
07 February 2007 (online)

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Abstract

Treatment of aryl halides with alkenylgallium dichlor­ide, prepared from GaCl3 and alkenylmagnesium bromide, in the presence of a catalytic amount of palladium provided cross-coup­ling products in good yields.

Key words

alkenylgallium - coupling reaction - aryl halide - palladium

    References

  • 1a Metal-Catalyzed Cross-Coupling Reactions   Diederich F. Stang PJ. Wiley-VCH; Weinheim: 1998. 
    Google Scholar
  • 1b Heck RF. Palladium Reagents in Organic Syntheses   Academic Press; New York: 1985. 
    Google Scholar
  • 1c Tsuji J. Palladium Reagents and Catalysts. Innovations in Organic Synthesis   Wiley; Chichester U.K.: 1996. 
    Google Scholar
  • 2a Miyaura N. Suzuki A. Chem. Rev.  1995,  95:  2457 
    Google Scholar
  • 2b

    Suzuki, A., in ref. [1a] , Chapter 2.

  • Methylation of aryl chloride with methylgallium compounds were reported:
  • 3a Blum J. Berlin O. Milstein D. Ben-David Y. Wassermann BC. Schutte S. Schumann H. Synthesis  2000,  571 
    CrossrefGoogle Scholar
  • 3b Gelman D. Schumann H. Blum J. Tetrahedron Lett.  2000,  41:  7555 
    CrossrefGoogle Scholar
  • 4 A similar cine coupling was observed in the Hiyama coupling. See: Ikenaga K. Kikukawa K. Matsuda T. J. Chem. Soc., Perkin Trans. 1  1986,  1959 
    CrossrefGoogle Scholar
  • 5 Mikami S. Fujita K. Nakamura T. Yorimitsu H. Shinokubo H. Matsubara S. Oshima K. Org. Lett.  2001,  3:  1853 
    CrossrefGoogle Scholar