Oxidative esterification of primary alcohols with TEMPO/CaCl2/Oxone under hydrous conditions

Abstract

Symmetric esters are important compounds in the chemical industry, which creates demand for simple and efficient synthetic routes. Oxidative esterification is a promising method to achieve these aims. Here, we show that TEMPO/CaCl2/Oxone forms a convenient catalytic system for the synthesis of the aforementioned symmetric esters from primary alcohols in a biphasic dichloromethane–water solvent mixture. The substrate scope of the reaction method is complementary to those previously published and the terminal oxidant appears to play an important role. In addition, the method is shown to oxidize thiols preferentially over alcohol functional groups to give disulfide-bridged compounds.