Ni-Catalyzed Redox-Neutral Ring-Opening/Radical Addition/Ring-Closing Cascade of Cycloketone Oxime Esters and Vinyl Azides

A nickel-catalyzed iminyl radical-triggered C-C bond cleavage/radical addition/cyclization cascade of oxime esters and vinyl azides is described. This protocol enables rapid access to the cyanoalkylated 3,4-dihydro-2 H-pyrroles and phenanthridines in good yields via adjustment of the substrate's properties. Moreover, these reactions proceed under mild and redox-neutral conditions with a board substrate scope and excellent functional group tolerance.