Palladium-Catalyzed 1,1-Oxamidation and 1,1-Diamination of Unactivated Alkenyl Carbonyl Compounds.

Catalytic 1,1-difunctionalization of unactivated alkenes with two nucleophiles has attracted a great deal of interest but remains a challenge in synthetic chemistry. Here, palladium(II)-catalyzed Nu/Nu'-type 1,1-oxamidation and 1,1-diamination of unactivated alkenyl carbonyl compounds followed by amination are described. The distinguishing features of this reaction include the lack of a directing group, good functional group tolerance, and easily operational catalytic reaction conditions. Mechanistic investigations support a unique route involving two consecutive nucleopalladations for this 1,1-difunctionalization.