Abstract
AbstractA series of bidentate oxazoline‐NHC ligands has been synthesized in which the two heterocycles are connected by a CH2 linker. The corresponding rhodium(I) complexes were prepared by direct deprotonation of the imidazolium halide salts followed by the addition of a solution of [Rh(nbd)Cl]2 at low temperature. The cationic square planar rhodium complexes were generated by halide abstraction via addition of an excess of KPF6 in a CH2Cl2/water solvent system. Alternatively, the deprotonation of the imidazolium hexafluorophosphates and reaction with [Rh(nbd)Cl]2 directly gave the complex cations. These as well as oxazoline‐NHC systems, in which the two heterocycles are directly connected or through a CMe2 bridge, were investigated in the rhodium‐catalyzed hydrosilylation of acetophenone. The comparison of the three ligand families showed that the catalysts obtained by direct coupling of oxazolines and N‐heterocyclic carbenes, generating highly rigid chelate ligands, remain the most efficient systems giving the secondary alcohols in high enantioselectivity.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
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