A highly efficient iodine anion catalyzed cross-dehydrogenative aromatization of cyclohexenones with amines has been developed under metal-free conditions, which affords aromatic amines in good to excellent yields with a broad substrate scope. Meanwhile, this reaction provides a new method for the construction of C(sp 2 )-N bonds and also a new strategy for slow generation of oxidants or electrophiles via in situ dehalogenation. Moreover, this protocol affords a rapid and concise approach to chiral NOBIN derivatives.