Ligand-controlled chemoselective nickel-catalyzed cross-electrophile coupling of cyclic anhydrides with alkyl bromides

Abstract

The introduction of chemoselective transition-metal-catalyzed cross-electrophile coupling approaches continues to expand chemists’ pallet of C–C bond-forming reactions. Herein, a Ni-catalyzed ligand-controlled divergent chemoselective cross-electrophile coupling reaction of meso-anhydrides with unactivated alkyl bromides has been developed. Depending on the choice of ligand, both γ-keto acid and decarbonylated β-alkylated acid derivatives were obtained from the same feedstocks with excellent selectivity. The utility of these divergent transformations was demonstrated by their broad functional group tolerance and applications in the synthesis of bioactive carboxylic acids.