N-heterocyclic carbenes derived from imidazolium salts or triazolium salts haven proven themselves as effective organocatalysts or sigma-donor ligands for transition metal catalysts.<br/>We are pleased to report an alternative synthetic route leading in two steps from primary amines to 1-aryl substituted 1,2,4-triazolium salts (Figure 1). The crucial step of this approach is a copper catalyzed quaternization of various 4-R-1,2,4-triazoles using diaryliodonium salts. Key features of the presented work are a reliable reaction protocol, short reaction times and high functional group tolerance, thus allowing the selective N-arylation of the triazole ring even in the presence of pyridine, pyrimidine and sulfide groups.

Copper(I) promoted N-arylation of 4-R-1,2,4-triazoles

ACS Fall 2021

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