Stereoselective Synthesis of Thiocyanato/Selenocyanato‐Containing <i>Z</i> ‐Vinyl Sulfides Via Tf <sub>2</sub> O/DMSO‐Promoted Sulfenofunctionalization of Alkynes

In this work, we developed a practical sulfonium‐salt mediated difunctionalization of alkynes with NH 4 SCN/KSeCN. This method enables the effective synthesis of various thiocyanato/selenocyanato (SCN/SeCN)‐containing vinyl sulfides using DMSO as a readily available methylthio source. The reaction exhibits excellent regio‐ and Z‐selectivity with a broad substrate scope and high functional group compatibility. Gram‐scale experiments and late‐stage functionalization further make this protocol quite attractive in organic synthesis.

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Publication Details

Journal
European Journal of Organic Chemistry
Published
2026-05-28
DOI
https://doi.org/10.1002/ejoc.70585
Primary Topic
Sulfur-Based Synthesis Techniques
Type
article
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article

Stereoselective Synthesis of Thiocyanato/Selenocyanato‐Containing Z ‐Vinyl Sulfides Via Tf 2 O/DMSO‐Promoted Sulfenofunctionalization of Alkynes

Xiang-Qin Xu, Zheng‐wu Tan, Hong Yang, Li‐Hua Yang et al.
European Journal of Organic Chemistry
Sulfur-Based Synthesis Techniques
article

Stereoselective Synthesis of Thiocyanato/Selenocyanato‐Containing Z ‐Vinyl Sulfides Via Tf 2 O/DMSO‐Promoted Sulfenofunctionalization of Alkynes

Xiang-Qin Xu, Zheng‐wu Tan, Hong Yang, Li‐Hua Yang, Long‐Yong Xie
article en

Abstract

In this work, we developed a practical sulfonium‐salt mediated difunctionalization of alkynes with NH 4 SCN/KSeCN. This method enables the effective synthesis of various thiocyanato/selenocyanato (SCN/SeCN)‐containing vinyl sulfides using DMSO as a readily available methylthio source. The reaction exhibits excellent regio‐ and Z‐selectivity with a broad substrate scope and high functional group compatibility. Gram‐scale experiments and late‐stage functionalization further make this protocol quite attractive in organic synthesis.

European Journal of Organic Chemistry
Hunan University of Science and Engineering (CN)
Openalex Percentile: Top 10%
Sulfur-Based Synthesis Techniques
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