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Synlett 2022; 33(19): 1925-1928
DOI: 10.1055/s-0042-1753041
DOI: 10.1055/s-0042-1753041
letter
Stereoselective Synthesis of (Z)-1,2-Bis(arylsulfanyl)ethenes with Calcium Carbide as a Solid Alkyne Source
The authors thank the National Natural Science Foundation of China (21462038) and Key Laboratory of Eco-Environment-Related Polymer Materials of the Ministry of Education of China for their financial support of this work.
Abstract
A concise stereoselective synthesis of (Z)-1,2-bis(arylsulfanyl)ethenes by the reaction of arylsulfonyl chlorides with calcium carbide in the presence of cuprous iodide as a catalyst is described. The salient features of this protocol are its use of an inexpensive and easily handled solid alkyne source as a surrogate for flammable and explosive gaseous acetylene, its commercially available starting materials, its high stereoselectivity, and its simple workup procedures. The stereochemical structure of a selected product was determined by single-crystal X-ray diffraction. This method can be extended to a gram scale.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0042-1753041.
- Supporting Information
Publication History
Received: 27 July 2022
Accepted after revision: 17 September 2022
Article published online:
17 October 2022
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