Issue 18, 2020
From the journal:

Organic Chemistry Frontiers

NBS-activated cross-dehydrogenative esterification of carboxylic acids with DMSO†

Ya Wu,a   Mengsha Zhang,a   Yanli Zhang,a   Mingyang Li,a   Weisheng Feng, ORCID logo a   Xiaoke Zhenga  and  Lin Tang ORCID logo *b  

* Corresponding authors

a School of Pharmacy & Collaborative Innovation Center for Respiratory Disease Diagnosis and Treatment & Chinese Medicine Development of Henan Province, Henan University of Chinese Medicine, Zhengzhou, Henan 450046, China

b College of Chemistry and Chemical Engineering, Xinyang Normal University, Xinyang, Henan 464000, China
E-mail: lintang@xynu.edu.cn

Abstract

The first N-bromosuccinimide (NBS)-promoted transition metal-free cross-dehydrogenative esterification of carboxylic acids with dimethyl sulfoxide (DMSO) has been disclosed for formal C–O formation via Pummerer-type rearrangement. These transformations employ readily available carboxylic acids as the nucleophile and DMSO as the sulfur-containing carbon source and solvent under mild conditions, affording valuable (methylsulfinyl)methyl esters with a broad substrate scope. Furthermore, the developed protocol provides an efficient and straightforward method for the preparation of deuterated (methylsulfinyl)methyl esters by use of deuterium-labelled DMSO as the reagent.

Graphical abstract: NBS-activated cross-dehydrogenative esterification of carboxylic acids with DMSO

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Article information

DOI
https://doi.org/10.1039/D0QO00617C
Article type
Research Article
Submitted
22 May 2020
Accepted
18 Aug 2020
First published
20 Aug 2020

Org. Chem. Front., 2020,7, 2719-2724

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NBS-activated cross-dehydrogenative esterification of carboxylic acids with DMSO

Y. Wu, M. Zhang, Y. Zhang, M. Li, W. Feng, X. Zheng and L. Tang, Org. Chem. Front., 2020, 7, 2719 DOI: 10.1039/D0QO00617C

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