Electrochemically Induced Synthesis of Substituted 5-Thiotetrazoles

A novel electrochemical procedure for the one-pot synthesis of variously substituted 5-thiotetrazole has been established by a three-component reaction (thiol(thiophenol)s, isocyanides, and azidotrimethylsilane). This approach is achieved by the sulfidation of isocyanide and subsequent cycloaddition with azidotrimethylsilane under mild conditions without a metal catalyst or external oxidant. Importantly, the presented methodology not only features a wide substrate scope but also exhibits the practicality showcased by gram-scale synthesis and various conversions.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2025-05-06
DOI
https://doi.org/10.1021/acs.joc.4c02822
Citations
3
Primary Topic
Sulfur-Based Synthesis Techniques
Type
article
Field-Weighted Citation Impact
2.81

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article

Electrochemically Induced Synthesis of Substituted 5-Thiotetrazoles

Bingcheng Hu, Bin Song, Feng Zhao, Pengxiang Gao et al.
3 citations
The Journal of Organic Chemistry
Sulfur-Based Synthesis Techniques
2.81
article

Electrochemically Induced Synthesis of Substituted 5-Thiotetrazoles

Bingcheng Hu, Bin Song, Feng Zhao, Pengxiang Gao, Chong Zhang
article en
3 citations

Abstract

A novel electrochemical procedure for the one-pot synthesis of variously substituted 5-thiotetrazole has been established by a three-component reaction (thiol(thiophenol)s, isocyanides, and azidotrimethylsilane). This approach is achieved by the sulfidation of isocyanide and subsequent cycloaddition with azidotrimethylsilane under mild conditions without a metal catalyst or external oxidant. Importantly, the presented methodology not only features a wide substrate scope but also exhibits the practicality showcased by gram-scale synthesis and various conversions.

The Journal of Organic ChemistryVol. 90(19)
Nanjing University of Science and Technology (CN)
National Natural Science Foundation of China
Openalex Percentile: Top 11%
Sulfur-Based Synthesis Techniques
2.81
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