Palladium-catalyzed unactivated ß-methylene C(sp(3))-H bond alkenylation of aliphatic amides and its application in a sequential C(sp(3))-H/C(sp(2))-H bond alkenylation.

A palladium(II)-catalyzed ß-methylene C(sp(3))-H bond alkenylation of acyclic aliphatic amides with alkenyl halides has been developed. Both (E)-olefins and (Z)-olefins can be readily accessed using this method and a possible (Z)/(E)-olefin isomerization pathway is proposed. A solvent effect-promoted sequential C(sp(3))-H bond alkenylation and C(sp(2))-H bond alkenylation was also studied, and can provide a convenient route to novel diene compounds.