Highly efficient cationic palladium catalyzed acetylation of alcohols and carbohydrate-derived polyols

Abstract

The development of a new facile method for the acetylation of alcohols and carbohydrate-derived polyols is described. This method relies on the nature of the cationic palladium catalyst, Pd(PhCN)2(OTf)2 which is generated in situ from Pd(PhCN)2Cl2and AgOTf to catalyze the acetylation reaction. This new acetylation protocol is very rapid and proceeds under mild conditions with only 1 mol% of catalyst loading at room temperature. This new method has been applied to a variety of different alcohols with different levels of steric hindrance, as well as carbohydrate-derived polyols to provide the corresponding fully acetylated products in excellent yields.