Iodine-Initiated Dioxygenation of Aryl Alkenes Using<i>tert</i>-Butylhydroperoxides and Water: A Route to Vicinal Diols and Bisperoxides

Abstract

An environment-friendly and efficient dioxygenation of aryl alkenes for the construction of vicinal diols has been developed in water with iodine as the catalyst and <i>tert</i>-butylhydroperoxides (TBHPs) as the oxidant. The protocol was efficient, sustainable, and operationally simple. Detailed mechanistic studies indicated that one of the hydroxyl groups is derived from water and the other one is derived from TBHP. Additionally, the bisperoxides could be obtained in good yields with iodine as the catalyst, Na₂CO₃ as the additive, and propylene carbonate as the solvent, instead.