Coupling Pd-Catalyzed Alcohol Oxidation to Olefin Functionalization:  Hydrohalogenation/Hydroalkoxylation of Styrenes

Abstract

A hydrochlorination reaction of styrenes catalyzed by Pd(II) in combination with Cu(II) was developed, which was followed by an in situ conversion of electron-rich products to an ether in the presence of an alcohol. Mechanistic experiments indicate that olefin functionalization is coupled to an alcohol oxidation, wherein a Pd hydride formed in the β-hydride elimination step of the alcohol oxidation was incorporated into the product.