Ru(II)-Catalyzed C–H Functionalization on Maleimides with Electrophiles: A Demonstration of Umpolung Strategy

The unconventional nucleophilic reactivity of maleimides, innate electrophiles, has been realized under Ru(II)-catalysis such that exposure to electrophiles delivered products of C–H chalcogenation and amidation in good yields (up to 94%). This protocol features mild conditions and operational simplicity with broad substrate scope, uses an inexpensive and air-stable catalyst, and also represents the first example of Ru(II) catalyzed C–H selenylation of alkenes.