First study on the enantioselective palladium-catalyzed C-P cross-coupling reaction between an alkenyltriflate and a phosphine-borane

In this article, we report the first example of a palladium-catalyzed asymmetric C-P cross-coupling reaction between a racemic secondary phosphine-borane, methylphenylphosphine-borane 1, and an achiral triflate. The influence of various parameters such as the structure of the chiral ligand, the temperature and the nature of the solvent on the activity and the selectivity of the reaction is reported. Enantiomeric ratios up to 78:22 were obtained using (S,S)-Me-DUPHOSPdCl2 as catalyst. A kinetic resolution process is proposed to account for this selectivity. (C) 2010 Academie des sciences. Published by Elsevier Masson SAS. All rights reserved.