Copper-Catalyzed O-Methylation of Carboxylic Acids Using DMSO as a Methyl Source

Jing Jia; Qing Jiang; An Zhao; Bin Xu; Qiang Liu; Wei-Ping Luo; Can-Cheng Guo

doi:10.1055/s-0035-1560967

Synthesis, Table of Contents

Synthesis 2016; 48(03): 421-428
DOI: 10.1055/s-0035-1560967

paper

Copper-Catalyzed O-Methylation of Carboxylic Acids Using DMSO as a Methyl Source

Jing Jia

College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, P. R. of China Email: ccguo@hnu.edu.cn

,

Qing Jiang

College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, P. R. of China Email: ccguo@hnu.edu.cn

,

An Zhao

College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, P. R. of China Email: ccguo@hnu.edu.cn

,

Bin Xu

College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, P. R. of China Email: ccguo@hnu.edu.cn

,

Qiang Liu

College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, P. R. of China Email: ccguo@hnu.edu.cn

,

Wei-Ping Luo

College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, P. R. of China Email: ccguo@hnu.edu.cn

,

Can-Cheng Guo*

College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, P. R. of China Email: ccguo@hnu.edu.cn

› Author Affiliations

Abstract

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Abstract

A copper-catalyzed O-methylation of carboxylic acids using dimethyl sulfoxide (DMSO) as the methyl source is disclosed. This transformation exhibits a broad substrate scope and excellent functional group tolerance. Mechanistic studies indicate that a methyl radical is generated from dimethyl sulfoxide in the reaction process.

Key words

carboxylic acids - O-methylation - dimethyl sulfoxide - hydrogen peroxide - methyl radical - esterification - esters

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References

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