(Diacetoxyiodo)benzene-Mediated C-H Oxidation of Benzylic Acetals

Abstract

A useful oxidation of C-H bond of benzylic acetals has been achieved. This method avoids the use of stoichiometric metals and is compatible with the presence of both electron-donating and electron-withdrawing substituents on the aromatic ring. Oxidation was carried out by rapid microwave irradiation of benzylic acetals with PhI(OAc)2 as the oxidant. This led to the oxidation of acetals into 2-acetoxy-1,3-dioxolanes. Furthermore, this transformation protocol encompasses a wide range of valuable conversions of these useful synthons into different carboxylic acid derivatives.