Nickel-Catalyzed Reductive Allyl-Aryl Cross-Electrophile Coupling via Allylic C-F Bond Activation.

Nickel-catalyzed reductive cross-coupling of allylic difluorides with aryl iodides was achieved via allylic C-F bond activation. Based on this protocol, a series of γ-arylated monofluoroalkenes were synthesized in moderate to high yields with high Z-selectivities. Mechanistic studies suggest that the C-I bonds of the aryl iodides and the C-F bonds of the allylic difluorides were cleaved via oxidative addition and β-fluorine elimination, respectively, where the oxidative addition of less reactive C-F bonds was avoided to permit their transformation.