Palladium nanoparticles generated from allylpalladium chloride in situ: A simple and highly efficient catalytic system for Mizoroki–Heck reactions

Abstract

The Mizoroki–Heck reactions of aryl halides catalyzed by palladium nanoparticles generated in situ from a simple allyl palladium precursor were investigated in argon. The high turnover numbers of 9,300,000 have been obtained with 4-bromobenzonitrile as substrate and 3500 with 4-nitrochlorobenzene. When the reaction was performed in air, a low yield was given, but it could be improved obviously by addition of PEG-400. The main reason was that inactive Pd(II) species could be rapidly reduced to the active Pd(0) by PEG. In other word, the existence of air and PEG led to a synergistic effect which the oxidation by air prevents the aggregation of Pd NPs and the reduction by PEG maintains the high activity of Pd(0) species.