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

Hasil Aman; Yen-Hsiang Wang; Gary Jing Chuang

doi:10.1021/acsomega.9b04009

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

ACS Omega. 2019 Dec 30;5(1):918-925. doi: 10.1021/acsomega.9b04009. eCollection 2020 Jan 14.

Authors

Hasil Aman¹, Yen-Hsiang Wang¹, Gary Jing Chuang¹

Affiliation

¹ Department of Chemistry, Chung Yuan Christian University, Chung-Li 32023, Taiwan.

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.