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

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 tra...

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Autores principales: Liu, Hongshi, Wang, Enhua, Yang, Juan, Peng, Mei, Gao, Ming, Jiang, Yangming, Hu, Enming, Liang, Guangyan, Yang, Lishou, Yang, Xiaosheng
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2022
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9673470/
https://www.ncbi.nlm.nih.gov/pubmed/36425198
http://dx.doi.org/10.1039/d2ra06618a
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author Liu, Hongshi
Wang, Enhua
Yang, Juan
Peng, Mei
Gao, Ming
Jiang, Yangming
Hu, Enming
Liang, Guangyan
Yang, Lishou
Yang, Xiaosheng
author_facet Liu, Hongshi
Wang, Enhua
Yang, Juan
Peng, Mei
Gao, Ming
Jiang, Yangming
Hu, Enming
Liang, Guangyan
Yang, Lishou
Yang, Xiaosheng
author_sort Liu, Hongshi
collection PubMed
description 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.
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spelling pubmed-96734702022-11-23 Autocatalytic methylthiomethylation of carboxylic acid/phenol involving the formation of DMSO enolate: convenient synthesis of methylthiomethyl ester/ether Liu, Hongshi Wang, Enhua Yang, Juan Peng, Mei Gao, Ming Jiang, Yangming Hu, Enming Liang, Guangyan Yang, Lishou Yang, Xiaosheng RSC Adv Chemistry 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. The Royal Society of Chemistry 2022-11-18 /pmc/articles/PMC9673470/ /pubmed/36425198 http://dx.doi.org/10.1039/d2ra06618a Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Liu, Hongshi
Wang, Enhua
Yang, Juan
Peng, Mei
Gao, Ming
Jiang, Yangming
Hu, Enming
Liang, Guangyan
Yang, Lishou
Yang, Xiaosheng
Autocatalytic methylthiomethylation of carboxylic acid/phenol involving the formation of DMSO enolate: convenient synthesis of methylthiomethyl ester/ether
title Autocatalytic methylthiomethylation of carboxylic acid/phenol involving the formation of DMSO enolate: convenient synthesis of methylthiomethyl ester/ether
title_full Autocatalytic methylthiomethylation of carboxylic acid/phenol involving the formation of DMSO enolate: convenient synthesis of methylthiomethyl ester/ether
title_fullStr Autocatalytic methylthiomethylation of carboxylic acid/phenol involving the formation of DMSO enolate: convenient synthesis of methylthiomethyl ester/ether
title_full_unstemmed Autocatalytic methylthiomethylation of carboxylic acid/phenol involving the formation of DMSO enolate: convenient synthesis of methylthiomethyl ester/ether
title_short Autocatalytic methylthiomethylation of carboxylic acid/phenol involving the formation of DMSO enolate: convenient synthesis of methylthiomethyl ester/ether
title_sort autocatalytic methylthiomethylation of carboxylic acid/phenol involving the formation of dmso enolate: convenient synthesis of methylthiomethyl ester/ether
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9673470/
https://www.ncbi.nlm.nih.gov/pubmed/36425198
http://dx.doi.org/10.1039/d2ra06618a
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