Journal
COMPTES RENDUS CHIMIE
Volume 13, Issue 8-9, Pages 1099-1103Publisher
ELSEVIER FRANCE-EDITIONS SCIENTIFIQUES MEDICALES ELSEVIER
DOI: 10.1016/j.crci.2010.06.003
Keywords
P-alkenylphosphines; Phosphine-boranes; Phosphine ligands; C-P cross-coupling; Enantioselectivity
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Funding
- Ministere de la Recherche et des Nouvelles Technologies
- Centre national de la recherche scientifique (CNRS)
- Region Basse-Normandie
- European Union
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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.
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