Electrochemically Induced Three-Component Synthesis of Substituted 5-Aminotetrazoles from Isocyanides, Amines, and Azides

A facile one-pot electrochemically induced addition-cyclization reaction of isocyanides, amines, and trimethylsilyl azide (TMSN3) has been established for the construction of diversely substituted 5-aminotetrazoles. This protocol enables efficient C-N and N-N bond formation under mild conditions, avoiding transition-metal catalysts and external oxidants. The reaction exhibits a broad substrate scope and good functional group compatibility, while a gram-scale experiment demonstrates the scalability of this electrochemical protocol.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2026-10-28
DOI
https://doi.org/10.1021/acs.joc.6c01999
Primary Topic
Synthesis of Tetrazole Derivatives
Type
article
Field-Weighted Citation Impact
0.00

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article

Electrochemically Induced Three-Component Synthesis of Substituted 5-Aminotetrazoles from Isocyanides, Amines, and Azides

Jun Shan Luo, Bing Li, Lin Zhang, Hong-Yu Wu
4 links
The Journal of Organic Chemistry
Synthesis of Tetrazole Derivatives
article

Electrochemically Induced Three-Component Synthesis of Substituted 5-Aminotetrazoles from Isocyanides, Amines, and Azides

Jun Shan Luo, Bing Li, Lin Zhang, Hong-Yu Wu
article en

Abstract

A facile one-pot electrochemically induced addition-cyclization reaction of isocyanides, amines, and trimethylsilyl azide (TMSN3) has been established for the construction of diversely substituted 5-aminotetrazoles. This protocol enables efficient C-N and N-N bond formation under mild conditions, avoiding transition-metal catalysts and external oxidants. The reaction exhibits a broad substrate scope and good functional group compatibility, while a gram-scale experiment demonstrates the scalability of this electrochemical protocol.

The Journal of Organic Chemistry
Nanjing University of Science and Technology (CN)
National Natural Science Foundation of China
Openalex Percentile: Top 26%
Synthesis of Tetrazole Derivatives
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