Electron-Transfer-Induced Intermolecular [2+2] Cycloaddition Reactions Based on the Aromatic Redox Tag Strategy

Novel electron-transfer-induced intermolecular [2 + 2] cycloaddition reactions between an aliphatic cyclic enol ether and several unactivated olefins have been demonstrated on the basis of the aromatic redox tag strategy. The aromatic redox tag was oxidized during the formation of the cyclobutane ring, affording the relatively long-lived aromatic radical cation, which was then reduced to complete the overall reaction that constructed the corresponding [2 + 2] cycloadducts. The aromatic redox tag was also found to facilitate electron-transfer-induced cycloreversion reactions of cyclobutane rings.