A palladium(II)-catalyzed β-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.

A novel approach toward quaternary carbon centered cyclobutanes through Pd(ii)-catalyzed sequential intramolecular methylene C-H alkylation and intermolecular methine C-H bond arylation, alkenylation, alkylation, alkynylation, allylation, benzylation or alkoxylation is described. These quaternary carbon centered cyclobutanes could be further diversified through Pd(ii)-catalyzed γ-C(sp)-H bond activations. The synthetic utility of this novel approach was exemplified by its application to the synthesis of a bioactive small molecule.

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