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

A new copper-catalyzed aerobic hydroxyamination of alkenes of unsaturated keto oximes with O-2 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.

Automated summary

This study presents a new copper-catalyzed method for the aerobic hydroxyamination of unsaturated keto oximes with O-2 in EtOH, producing functionalized cyclic nitrones. The method is characterized by its easy operation, discharge of water as a byproduct, use of green molecular oxygen as the oxygen atom source and terminal oxidant, inexpensive copper salt as the catalyst, low-cost environmentally friendly ethanol as the medium, and excellent selectivity, broad substrate scope, and functional group tolerance.