Herein, we report an azobis(isobutyronitrile) (AIBN)-promoted radical α-cyanation of formed imine under atmospheric O. This oxidative radical addition (ORA) procedure proceeds with the sequential homocleavage of AIBN, extrusion of N, and capture of O toward an O-centered radical, which is converted to a cyano radical by β-scission. Then, the insertion of the cyano radical into the imine C═N bond forms an aminyl radical, leading to α-cyano imine after 1,2-hydrogen atom transfer (HAT) and H abstraction. Such a transition-metal-free procedure features mild reaction conditions and a broad substrate scope, employing molecular O as a clean terminal oxidant.
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