Palladium-catalyzed unactivated β-methylene C(sp3)–H bond alkenylation of aliphatic amides and its application in a sequential C(sp3)–H/C(sp2)–H bond alkenylation

Abstract

A palladium(II)-catalyzed β-methylene C(sp³)–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(sp³)–H bond alkenylation and C(sp²)–H bond alkenylation was also studied, and can provide a convenient route to novel diene compounds.