External-oxidant-free amino-benzoyloxylation of unactivated alkenes of unsaturated ketoximes with O-benzoylhydroxylamines

A new copper-catalyzed two-component amino-benzoyloxylation of unactivated alkenes of unsaturated ketoximes with O-benzoylhydroxylamines as the benzoyloxy sources is developed. Chemoselectivity of this method toward amino-benzoyloxylation or oxy-benzoyloxylation of alkenyl ketoximes relies on the position of the tethered olefins, and provides an external-oxidant-free alkene difunctionalization route that directly utilizes O-benzoylhydroxylamines as the benzoyloxy radical precursors and internal oxidants for the divergent synthesis of cyclic nitrones and isoxazolines.

Automated summary

This new method involves a copper-catalyzed two-component amino-benzoyloxylation of unactivated alkenes using O-benzoylhydroxylamines as benzoyloxy sources. The chemoselectivity of the reaction depends on the position of the tethered olefins, providing a way for external-oxidant-free alkene difunctionalization. It directly utilizes O-benzoylhydroxylamines as benzoyloxy radical precursors and internal oxidants for synthesizing cyclic nitrones and isoxazolines.