Suzuki-Miyaura reactions of aryl chloride derivatives with arylboronic acids using mesoporous silica-supported aryldicyclohexylphosphine

Abstract

The Suzuki-Miyaura reactions using mesoporous-supported aryldicyclohexylphosphine as ligand have been investigated. The catalysts were based on SBA-15 type mesoporous silica which was transformed in a four-step synthesis leading to a phosphine-containing hybrid material The most productive catalytic system studied was generated in situ from this material and the homogeneous palladium complex, Pd(OAc)2. Other catalytic systems were studied for comparison [homogeneous cataysts, a "preformed" catalyst obtained by reaction of PdCl2 (PhCN)2 and the phosphine-containing material]. Variations involving the solvent system, the substrate aryl chloride and the arylboronic acid reactant were also studied. For both in situ and preformed cataiyst systems, high conversions and yields are obtained for activated aryl chlorides. Success of the reaction for unactivated aryl chlorides was limited to the catalyst formed in situ. The catalyst formed in situ was also shown to be reactive under aqueous reaction conditions in the cross-coupling of 1-(4-chlorophenyl)ethanone with phenylboronic acid. © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.