Nickel-Catalyzed Remote Arylation of Alkenyl Aldehydes Initiated by Radical Alkylation with Tertiary alpha-Carbonyl Alkyl Bromides

A novel nickel-catalyzed remote arylation of alkenyl aldehydes triggered by radical alkylation with tertiary alpha-carbonyl alkyl bromides is described, thus producing a quaternary carbon center containing ketones in promising yields with broad functional group compatibility. Preliminary mechanistic studies suggest that the combination of a 1,n-HAT (n = 5 or 6) from alkyl radicals to aldehyde C-H bonds with nickel catalysis may account for the realization of this reaction.