Issue 37, 2021
From the journal:

Organic & Biomolecular Chemistry

Selective difunctionalization of electron-deficient alkynes: access to (E)-2-iodo-3-(methylthio)acrylate†

Ling-Hui Lu,a   Guangchuan Ou,a   Xiongjie Zhao,a   Yufei Wang,a   Xuelian Chen,a   Wenjun Liao,a   Shundan Lia  and  Chao Wu ORCID logo *a  

* Corresponding authors

a College of Chemistry and Bioengineering, Hunan University of Science and Engineering, Yongzhou 425100, China
E-mail: chwu_chem@yeah.net

Abstract

A convenient and efficient approach to (E)-2-iodo-3-(methylthio)acrylate has been developed through direct iodothiomethylation of alkynes with aqueous HI and DMSO under mild conditions. This novel protocol has demonstrated a unique difunctionalization of electron-deficient alkynes with a broad substrate scope and excellent functional-group tolerance. Preliminary mechanistic studies indicated that prior diiodination of alkynes, followed by nucleophilic substitution with in situ generated DMS led to the formation of (E)-2-iodo-3-(methylthio)acrylate.

Graphical abstract: Selective difunctionalization of electron-deficient alkynes: access to (E)-2-iodo-3-(methylthio)acrylate

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Article information

DOI
https://doi.org/10.1039/D1OB01287H
Article type
Paper
Submitted
02 Jul 2021
Accepted
25 Aug 2021
First published
26 Aug 2021

Org. Biomol. Chem., 2021,19, 8128-8132

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Selective difunctionalization of electron-deficient alkynes: access to (E)-2-iodo-3-(methylthio)acrylate

L. Lu, G. Ou, X. Zhao, Y. Wang, X. Chen, W. Liao, S. Li and C. Wu, Org. Biomol. Chem., 2021, 19, 8128 DOI: 10.1039/D1OB01287H

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