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

Hongshi Liu; Enhua Wang; Juan Yang; Mei Peng; Ming Gao; Yangming Jiang; Enming Hu; Guangyan Liang; Lishou Yang; Xiaosheng Yang

doi:10.1039/d2ra06618a

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

RSC Adv. 2022 Nov 18;12(51):33156-33159. doi: 10.1039/d2ra06618a. eCollection 2022 Nov 15.

Authors

Hongshi Liu^{1

2}, Enhua Wang³, Juan Yang^{1

2}, Mei Peng^{1

2}, Ming Gao^{1

2}, Yangming Jiang^{1

2}, Enming Hu^{1

2}, Guangyan Liang^{1

2}, Lishou Yang^{1

2}, Xiaosheng Yang^{1

2}

Affiliations

¹ State Key Laboratory of Functions and Applications of Medicinal Plants, Guizhou Medical University Guiyang 550014 P. R. China gzcnp@sina.cn 1039160204@qq.com.
² The Key Laboratory of Chemistry for Natural Products of Guizhou Province and Chinese Academy of Sciences Guiyang 550014 P. R. China.
³ Department of Food and Medicine, Guizhou Vocational College of Agriculture Qingzhen 551400 P. R. China.

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.