Download PDF
Synlett 2009(11): 1745-1748  
DOI: 10.1055/s-0029-1217379
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Palladium-Catalysed Carbonylative Cross-Coupling Reactions of Aryl Iodides and Vinyl Boron Derivatives as a Straightforward Route to Aryl Vinyl Ketones

Cyril Pirez, Julien Dheur, Mathieu Sauthier*, Yves Castanet*, André Mortreux
Université des Sciences et Technologies de Lille 1, Unité de Catalyse et Chimie du Solide, UMR CNRS 8181, ENSCL, B.P. 90108, 59652 Villeneuve dAscq Cedex, France
Fax: +33(3)20436585; e-Mail: mathieu.sauthier@univ-lille1.fr; e-Mail: yves.castanet@ensc-lille.fr;
Further Information

Publication History

Received 11 February 2009
Publication Date:
15 June 2009 (online)

    Permissions and Reprints All articles of this category

Abstract

The carbonylative cross-coupling of potassium vinyl trifluoroborate or 2,4,6-trivinyltricycloboroxane with aryl iodides under mild conditions affords aryl vinyl ketones. The optimisation of the reaction conditions leads to the targeted enones in good yields in the case of the aryl substrates bearing donor substituents in meta or para position. Much more moderate yields were observed with aryl substrates bearing withdrawing substituents.

Key words

carbonylation - cross-coupling - palladium - vinyl boron derivatives - enones.

    References and Notes

  • 1a Colquhoun HM. Thompson DJ. Twigg MV. In Carbonylation, Direct Synthesis of Carbonyl Compounds   Plenum Press; New York: 1991. 
    Google Scholar
  • 1b Topics in Organometallic Chemistry - Catalytic Carbonylation Reactions   Vol. 18:  Beller M. Springer; Berlin/Heidelberg: 2006. 
    Google Scholar
  • 2a Sauthier M. Castanet Y. Mortreux A. Chem. Commun.  2004,  1520 
    Google Scholar
  • 2b Chochois H. Sauthier M. Maerten E. Castanet Y. Mortreux A. Tetrahedron  2006,  62:  11740 
    Google Scholar
  • 3 Bianco A. Cavarischia C. Farina A. Guiso M. Marra C. Tetrahedron Lett.  2003,  44:  9107 
    CrossrefGoogle Scholar
  • 4a Maruoka K. Imoto H. Yamamoto H. J. Am. Chem. Soc.  1994,  116:  12115 
    Google Scholar
  • 4b O’Neill PM. Verissimo E. Ward SA. Davies J. Korshin EE. Araujo N. Pugh MD. Lurdes S. Cristiano M. Stocks PA. Bachi MD. Bioorg. Med. Chem. Lett.  2006,  16:  2991 
    Google Scholar
  • 5a Linton BR. Reutershan MH. Aderman CM. Richarson EA. Brownell KR. Ashley CW. Evans CA. Miller SJ. Tetrahedron Lett.  2007,  48:  1993 
    Google Scholar
  • 5b Liu T.-Y. Li R. Chai Q. Long J. Li B.-J. Wu Y. Ding L.-S. Chen Y.-C. Chem. Eur. J.  2007,  13:  319 
    Google Scholar
  • 6a Rodriguez-Castro M. Cesteros LC. Katime I. Nuno-Donlucas SM. J. Polym. Sci., Part B: Polym. Phys.  2006,  44:  2404 
    Google Scholar
  • 6b Cheng C. Sun G. Khoshdel E. Wooley KL. J. Am. Chem. Soc.  2007,  129:  10086 
    Google Scholar
  • 7a Couve-Bonnaire S. Carpentier J.-F. Mortreux A. Castanet Y. Tetrahedron Lett.  2001,  42:  3689 
    Google Scholar
  • 7b Couve-Bonnaire S. Carpentier J.-F. Mortreux A. Castanet Y. Tetrahedron  2003,  59:  2793 
    Google Scholar
  • 7c Maerten E. Hassouna F. Couve-Bonnaire S. Mortreux A. Carpentier J.-F. Castanet Y. Synlett  2003,  1874 
    Google Scholar
  • 7d Maerten E. Sauthier M. Castanet Y. Mortreux A. Tetrahedron  2007,  63:  682 
    Google Scholar
  • 8 Matteson DS. J. Am. Chem. Soc.  1960,  82:  4228 
    CrossrefGoogle Scholar
  • 9a Darses S. Michaud G. Genêt J.-P. Tetrahedron Lett.  1998,  39:  5045 
    Google Scholar
  • 9b Murphy JM. Tzschucke CC. Hartwig JF. Org. Lett.  2007,  9:  757 
    Google Scholar
  • 10 Kerins F. O’Shea DF. J. Org. Chem.  2002,  67:  4968 
    CrossrefPubMedGoogle Scholar
  • 11a Molander GA. Rivero MR. Org. Lett.  2002,  4:  107 
    Google Scholar
  • 11b Molander GA. Brown AR. J. Org. Chem.  2006,  71:  9681 
    Google Scholar
  • 13a Hayashi T. Yamasaki K. Chem. Rev.  2003,  103:  2829 
    Google Scholar
  • 13b Pucheault M. Daeses S. Genêt J.-P. Eur. J. Org. Chem.  2002,  3552 
    Google Scholar
  • 14 See, for example : Miyaura N. In Metal-Catalyzed Cross-Coupling Reactions   2nd ed.:  De Meijere A. Diederich F. Wiley-VCH; Weinheim: 2004. 
    Google Scholar
12

Abbreviations: dppe = 1,2-bis(diphenylphosphino)ethane, ddpp = 1,2-bis(diphenylphosphino)propane, dppb = 1,2-bis(diphenylphosphino)butane, dppf = 1,2-bis(diphenyl-phosphino) ferrocene.