Tetrazoles are nitrogen-rich heterocyclic compounds having a variety of applications in energetics, synthetic organic, medicinal, and material chemistry. Several methodologies have been developed for the synthesis of tetrazole scaffolds, which include the classical [3+2] cycloaddition of azides and the corresponding cyanides under various reaction conditions. But, most of these cycloadditions have drawbacks due to the use of toxic metal catalysts and in-situ generation of the hazardous hydrazoic acid (HN<sub>3</sub>). Herein we describe our efforts on the [3+2] cycloaddition reaction of sodium azide and aryl/aliphatic cyanides with minimal generation of HN<sub>3</sub>, utilizing the acidity of the catalytic amount of trialkylamine hydrochloride and a quaternary ammonium salt as phase transfer agent in a non-polar reaction medium. This modified solid-liquid phase transfer catalytic process produced tetrazole products in very good to excellent isolated yields. The details of the studies will be presented.

A metal-free catalytic approach towards the synthesis 5- substituted tetrazoles with the minimal in-situ generation of the toxic hydrazoic acid

ACS Fall 2021

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