Arylation of Click Triazoles with Diaryliodonium Salts

J Org Chem. 2019 Nov 1;84(21):14030-14044. doi: 10.1021/acs.joc.9b02197. Epub 2019 Oct 10.

Abstract

A robust, selective, and highly efficient method for the preparation of 1,3,4-triaryl 1,2,3-triazolium salts has been developed. It features arylation of a click triazole with a diaryliodonium salt in the presence of a copper catalyst under neat conditions. The presence of pyridine functionality is tolerated, enabling the first access to key precursors of pyridyl-mesoionic carbene ligands. The method has been integrated into a one-pot protocol with terminal alkyne, sodium azide, and diaryliodonium salt as starting compounds.