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Synthesis of 1,2,2-trifluorovinyl sulphides and selenides from trifluorovinylation of organic thiocyanates and selenocyanates

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Abstract

A nucleophilic trifluorovinylation of organothiocyanates catalyzed by tetrabutylammonium fluoride has been developed. In this transformation, a variety of aryl and alkyl thiocyanates reacted with trifluorovinyl trimethylsilane to afford 1,2,2-trifluorovinyl sulphides. This transformation was extended to organic selenocyanates to afford 1,2,2-trifluorovinyl selenides. The presented methodology is simple and mild, and can also be used to prepare 1,2,2-trifluorovinyl sulphoxides from organothiocyanates.

Graphical abstract: Synthesis of 1,2,2-trifluorovinyl sulphides and selenides from trifluorovinylation of organic thiocyanates and selenocyanates

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Publication details

The article was received on 17 Jul 2017, accepted on 16 Aug 2017 and first published on 16 Aug 2017


Article type: Research Article
DOI: 10.1039/C7QO00595D
Citation: Org. Chem. Front., 2017, Advance Article
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    Synthesis of 1,2,2-trifluorovinyl sulphides and selenides from trifluorovinylation of organic thiocyanates and selenocyanates

    Y. Zhang, D. Wu and Z. Weng, Org. Chem. Front., 2017, Advance Article , DOI: 10.1039/C7QO00595D

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