Iodine(III)‐Mediated Oxidation of Anilines to Construct Dibenzazepines**

Abstract The development of an efficient process that produces bioactive medium‐sized N ‐heterocyclic scaffolds from 2‐substituted anilines using either iodosobenzene or (bis(trifluoroacetoxy)iodo)‐benzene is reported. The tether between the sulfonamide and the aryl group can be varied to access dihydroacridine‐, dibenzazepine‐, or dibenzazocine scaffolds. While substitution on the aniline portion is limited to electron‐neutral‐ or electron‐poor groups, a broader range of functional groups are tolerated on the ortho ‐aryl substituent and site selective C−NAr bond formation can be achieved. Preliminary mechanistic investigations suggest that medium‐ring formation occurs via radical reactive intermediates.