Nickel-Catalyzed Reductive Electrophilic Ring Opening of Cycloketone Oxime Esters with Aroyl Chlorides

By merging cross-electrophile coupling and C–C bond cleavage, we developed a Ni-catalyzed electrophilic ring opening of cycloketone oxime esters with aromatic acid chlorides in assistance of Mn as reductant. Notably, complete regioselectivity can be achieved in this C–C bond cleavage reaction, providing an efficient access to a variety of cyanoketones under cyanide-free conditions. A radical reaction pathway was proposed on the basis of the results of the mechanistic probing experiments.