Palladium-catalyzed allylic alkylation of simple ketones with allylic alcohols and its mechanistic study

Abstract

Allylic alcohols were directly used in Pd-catalyzed allylic alkylations of simple ketones under mild reaction conditions. The reaction proceeded smoothly at 20 °C by the concerted action of a Pd catalyst, a pyrrolidine co-catalyst, and a hydrogen-bonding solvent, and does not require any additional reagents. A computational study suggested that methanol plays a crucial role in the formation of the π-allylpalladium complex by lowering the activation barrier.

Keywords: DFT calculation; allylic alcohol; allylic alkylation; organocatalysis; palladium.