Palladium-Catalyzed Oxidative Coupling of Aromatic Primary Amines and Alkenes under Molecular Oxygen: Stereoselective Assembly of (Z)-Enamines

An efficient Pd-catalyzed oxidative coupling of aromatic primary amines and alkenes under molecular oxygen is disclosed. Under mild reaction conditions, it provides a rapid access to (Z)-enamine compounds with exceptional functional group tolerance and excellent regio- and stereoselectivity. This attractive route is of great significance due to its applicability to a wide range of aromatic primary amines, most of which could not be efficiently converted into enamines previously. Moreover, this protocol is scalable, and the resultant enamines could be conveniently transformed into a series of N-containing heterocyclics, thus illustrating its potential applications in synthetic and medicinal chemistry.