Radical additions of aryl iodides to arenes are facilitated by oxidative rearomatization with dioxygen.

Inter- and intramolecular additions of aryl radicals derived from aryl iodides to arenes are promoted by tris(trimethylsilyl)silane and occur under exceptionally mild conditions (15-30 min at 25 degrees C) in nondegassed benzene. A chain mechanism involving reaction of the intermediate cyclohexadienyl radical with oxygen to directly generate the aromatized product and the hydroperoxy radical is proposed.