Palladium-catalyzed carbonylative coupling of benzyl chlorides with aryl boronic acids in aqueous media

A novel chemoselective protocol for the carbonylative Suzuki coupling of benzyl chlorides with aryl boronic acids at low pressure of carbon monoxide has been developed. Applying a commercially available palladium acetate/PCy3 catalyst system in the presence of potassium phosphate as the base and water as the solvent the coupling reactions proceeded smoothly. To demonstrate the general applicability 12 different alpha-arylated acetophenones have been synthesized in moderate to good yields (41-78%) under mild conditions. (C) 2010 Elsevier Ltd. All rights reserved.