Issue 28, 2014
From the journal:

Chemical Communications

N-Heterocyclic carbene-catalyzed formal cross-coupling reaction of α-haloenals with thiols: organocatalytic construction of sp2 carbon–sulfur bonds†

Lin He,*a   Hao Guo,a   Yuan-Zhen Li,a   Guang-Fen Dua  and  Bin Dai*a  

* Corresponding authors

a Key Laboratory for Green Processing of Chemical Engineering of Xinjiang Bingtuan, School of Chemistry and Chemical Engineering, Shihezi University, Xinjiang Uygur Autonomous Region, China
E-mail: helin@shzu.edu.cn, db_tea@shzu.edu.cn
Fax: +86-993-2057270

Abstract

A novel N-heterocyclic carbene (NHC)-catalyzed formal cross-coupling reaction between α-haloenals and thiols was developed. In the presence of 5 mol% NHC precursors and 1.6 equiv. potassium carbonate, various thiols coupled with α-haloenals to produce α-thioenals in 53% to 91% yield and excellent Z-selectivity.

Graphical abstract: N-Heterocyclic carbene-catalyzed formal cross-coupling reaction of α-haloenals with thiols: organocatalytic construction of sp2 carbon–sulfur bonds

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Article information

DOI
https://doi.org/10.1039/C4CC00154K
Article type
Communication
Submitted
08 Jan 2014
Accepted
11 Feb 2014
First published
13 Feb 2014

Chem. Commun., 2014,50, 3719-3721

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N-Heterocyclic carbene-catalyzed formal cross-coupling reaction of α-haloenals with thiols: organocatalytic construction of sp2 carbon–sulfur bonds

L. He, H. Guo, Y. Li, G. Du and B. Dai, Chem. Commun., 2014, 50, 3719 DOI: 10.1039/C4CC00154K

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