Copper-catalyzed primary amination of arene C H bond with hydroxylamine derivative

A novel methodology for the primary amination of aromatic C(sp2)-H bond utilizing hydroxylamine derivative as ammonia surrogates has been developed. With a cost-effective and convenient copper oxide, a variety of aromatic primary amines were synthesized without external oxidant with moderate to good yields under the mild conditions. This amination exhibits excellent functional group tolerance, wide substrate scope, the use of readily available substrates, and a facile work-up procedure. Furthermore, the late-stage modification of drug-like small molecules with complex structures was also allowed.