Copper-catalyzed aerobic hydroxyamination of alkenes of unsaturated keto oximes in EtOH toward cyclic nitrones

Abstract

A new copper-catalyzed aerobic hydroxyamination of alkenes of unsaturated keto oximes with O₂ in EtOH for producing functionalized cyclic nitrones is presented. Mechanistic studies indicate that this method involves radical initiation from the oxime side and superoxide radical formation. This method is distinguished by its easy operation with the discharge of water as the attendant product, its use of green molecular oxygen as the oxygen atom source and terminal oxidant, inexpensive copper salt as the catalyst and low-cost environmentally benign EtOH as the medium, and its exquisite selectivity, broad substrate scope, and excellent functional group tolerance.