Chemoselective benzylic oxidation of alkyl-substituted aromatics with singlet molecular oxygen generated from trans-3,5 hydroperoxy-3,5 dimethyl-1,2-dioxolan-3-yl ethaneperoxate

Abstract

Chemoselective benzylic oxidation of alkyl-substituted aromatics to carbonyl compounds was efficiently achieved with singlet molecular oxygen generated from trans-5-hydroperoxy-3,5-dimethyl-1,2-dioxolane-3-yl ethaneperoxate. The singlet molecular oxygen was generated in situ from fragmentation trans-5-hydroperoxy-3,5-dimethyl-1,2-dioxolane-3-yl ethaneperoxate in the presence of KOH. All the reactions proceeded smoothly at room temperature to afford the products in good-to-excellent yields within short reaction times. Also, the method is compatible with functional groups including, amines, sulfides, and allylic CH2.