Autocatalytic methylthiomethylation of carboxylic acid/phenol involving the formation of DMSO enolate: convenient synthesis of methylthiomethyl ester/ether

Abstract

This work reported a simple and practical protocol for the preparation of methylthiomethyl (MTM) esters/ethers directly from carboxylic acid/phenol and dimethylsulfoxide (DMSO) as solvent and methylthiomethyl source. With different types of carboxylic acids/phenols the reactions underwent smooth transformation to afford the corresponding MTM esters/ethers in moderate to excellent yields. This method features catalyst-free, easy to operate, broad substrate scope, good functional group tolerance and involvement of the formation of DMSO enolate.