Copper-Catalyzed Intermolecular C(sp2)-H Amination with Electrophilic O-Benzoyl Hydroxylamines

A copper-catalyzed intermolecular electrophilic amination of benzamides with O-benzoyl hydroxylamines was achieved with the assistance of an 8-aminoquinolyl group. With this protocol, good compatibility was observed for a variety of aryl amides and heteroaryl amides, and excellent tolerance with various functional groups was achieved. Significantly, the monoaminated product was overwhelmingly delivered under the simple reaction conditions. Preliminary mechanistic investigations suggested that a radical pathway should be excluded and C-H activation be potentially the rate-determining step.

Automated summary

The copper-catalyzed intermolecular electrophilic amination of benzamides with O-benzoyl hydroxylamines was successfully achieved with the assistance of an 8-aminoquinolyl group, showing good compatibility with various aryl amides and heteroaryl amides as well as excellent tolerance to different functional groups. The monoaminated product was predominantly obtained under simple reaction conditions, and preliminary mechanistic investigations suggested C-H activation to potentially be the rate-determining step.