Tetrazole Synthesis via Cyclopropenium Phase-Transfer Catalysis: A Click Strategy

Morden organic synthesis prizes efficiency, robustness, and generality─hallmarks of click chemistry. Here, we introduce a metal-free catalytic method for synthesizing diverse tetrazole heterocycles from simple, shelf-stable precursors. Central to this powerful strategy is leveraging cyclopropenium ions as phase-transfer catalysts, providing a practical and efficient approach to tetrazoles from nitriles and azides. The scope, mechanism, and synthetic utility of this methodology are detailed, highlighting its potential to expand the click chemistry tool box for heterocycle synthesis.

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Publication Details

Journal
Organic Letters
Published
2026-01-30
DOI
https://doi.org/10.1021/acs.orglett.5c05152
Primary Topic
Synthesis of Tetrazole Derivatives
Type
article
Field-Weighted Citation Impact
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article

Tetrazole Synthesis via Cyclopropenium Phase-Transfer Catalysis: A Click Strategy

Srini Vemulapalli, Travis C. Dudding
Organic Letters
Synthesis of Tetrazole Derivatives
article

Tetrazole Synthesis via Cyclopropenium Phase-Transfer Catalysis: A Click Strategy

Srini Vemulapalli, Travis C. Dudding
article en

Abstract

Morden organic synthesis prizes efficiency, robustness, and generality─hallmarks of click chemistry. Here, we introduce a metal-free catalytic method for synthesizing diverse tetrazole heterocycles from simple, shelf-stable precursors. Central to this powerful strategy is leveraging cyclopropenium ions as phase-transfer catalysts, providing a practical and efficient approach to tetrazoles from nitriles and azides. The scope, mechanism, and synthetic utility of this methodology are detailed, highlighting its potential to expand the click chemistry tool box for heterocycle synthesis.

Organic LettersVol. 28(6)
Brock University (CA)
Openalex Percentile: Top 72%
Synthesis of Tetrazole Derivatives
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