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

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journal contribution
posted on 24.08.2021, 17:37 by Suman Dana, Chandan Kumar Giri, Mahiuddin Baidya
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.