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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;
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Publication History

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

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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.

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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.