Anaerobic Palladium‐Catalyzed Chemoselective Oxidation of Allylic and Benzylic Alcohols with α‐Bromo Sulfoxide as a Co‐oxidant

Abstract

AbstractA chemoselective palladium‐catalyzed anaerobic oxidation of allylic and benzylic alcohols using an α‐bromo sulfoxide as a co‐oxidant is described for the first time. The catalyst system is simple and has a long life because of the allowance of phosphane ligands under the non‐aerobic conditions. The advantages of the described method include no overoxidation of primary alcohols to carboxylic acids because of the mild conditions applied, the tolerance of oxygen‐sensitive functionalities such as a carbon‐carbon double bond, an organothio group, or a diorganoamino group and the effective preparation of α,β‐unsaturated aldehydes and ketones, resulting from the oxidation of primary and secondary allylic alcohols, since a competitive Heck reaction with the co‐oxidant does not occur.