Copper-Catalyzed Aerobic Oxidative C–C Bond Cleavage of Unstrained Ketones with Air and Amines

A unique copper-catalyzed aerobic oxidative C–C bond cleavage of simple unstrained ketones with air and amines has been developed. In this chemistry, amides and oxo amides are easily synthesized through the selective C–C bond cleavage of simple ketones or unstrained cycloketones. The broad substrate scopes and use of an inexpensive copper catalyst and green molecular oxygen as an oxidant as well as an O-source make this protocol very attractive for potential synthetic applications. The control experiments reveal that the present copper-catalyzed oxidative C–C bond cleavage of simple ketones proceeds in a novel catalytic pathway rather than through the cleavage of a dioxetane intermediate.