The synthesis and characterisation of immobilised palladium carbene complexes and their application to heterogeneous catalysis

Silica supported palladium NHC complexes have been prepared by two different routes: one involving the reaction of silica-supported imidazolium salts with palladium acetate and a direct immobilisation of a pre-formed complex by reacting a (trimethoxysilylpropyl)-N-aryl-imidazolylidene palladium complex with surface hydroxyl groups. A small range of catalysts of varying steric bulk were prepared in order to evaluate the effect on catalytic conversion. The activity of the palladium catalysts in Suzuki cross-coupling reactions has been established. The catalysts prepared by immobilising pre-formed palladium complexes gave superior results for the conversion of aryl bromides and aryl chlorides. In addition, use of sterically bulky NHCs (such as the N-2,6-(diisopropyl) phenyl-substituted ligand) resulted in increased catalytic activity, which is analogous to the trends noted in homogeneous catalysis. (C) 2011 Elsevier B. V. All rights reserved.