Ruthenium(II)-Catalyzed Regioselective C-H Olefination of Aromatic Ketones and Amides with Allyl Sulfones

A Ru(II)-catalyzed cross-dehydrogenative Heck-type olefination of arenes with allyl sulfones leveraging the assistance of weakly coordinating ketone and amide functional groups is reported. It features a distinct reactivity profile in comparison to other allylic congeners, where β-sulfonyl elimination was not detected. The ambiphilic nature of the allyl sulfone side chain has also been demonstrated through intramolecular aza-Michael addition and aldol condensation. Mechanistic studies indicated the involvement of a reversible metalation step, where β-hydride elimination takes place selectively from the benzylic position.