Visible light-driven regioselective tert-butyl peroxidation and hydroperoxidation of alkenes using TBHP

Abstract

We report a visible-light-driven, photocatalyst-free bisperoxidation of aryl alkenes with tert-butyl hydroperoxide (TBHP), enabling the regioselective synthesis of α,β-bisperoxides. To our knowledge, this represents the first radical reaction utilizing TBHP as a dual source of tert-butylperoxy and hydroperoxy groups. This representative transformation helps reveal the practical value that this method may possess for rapid and reliable access to bisperoxidation substances under mild reaction conditions. In addition, when allyl benzene and its derivatives were used as reactants, allyl substituted peroxyl alcohol products were obtained. The mechanistic studies reveal that the hydroperoxyl group derives from conversion of the tert-butyl peroxide group using TBHP.