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 °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.