Nickel- and Lewis Acid-Catalyzed Intramolecular Iminocyanation of Alkenes via N(sp ² )–CN Activation

An intramolecular iminocyanation of alkenes via N(sp²)-CN cleavage of <i>N</i>-cyanimines promoted by cooperative Ni/Al catalysis is herein reported. This protocol allows the simultaneous introduction of both imino and cyano groups across an alkene, resulting in the formation of pyrroline derivatives with a pendant cyano functionality. Subsequent transformations of these motifs into pyrroline and pyrrolidine derivatives are also demonstrated. Preliminary mechanistic studies suggest a possible single-electron transfer pathway and radical cyclization.