6533b824fe1ef96bd1280280

RESEARCH PRODUCT

Anaerobic Palladium-Catalyzed Chemoselective Oxidation of Allylic and Benzylic Alcohols with α-Bromo Sulfoxide as a Co-Oxidant.

subject

description

A 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.