Sequential one-pot three-step synthesis of polysubstituted 4-(5-(trifluoromethyl)-1H-pyrazol-4-yl)-1H-1,2,3-triazole systems

Abstract

This work reports a successful one-pot three-step protocol for the synthesis of a new series of 15 examples of polysubstituted 4-(5-(trifluoromethyl)-1H-pyrazol-4-yl)-1H-1,2,3-triazoles, in which sequential Sonogashira cross-coupling, desilylation, and a copper(I)-catalyzed azide–alkyne cycloaddition reaction (CuAAC) with an overall yield of up to 72% were used. The presence of a trifluoromethyl substituent attached to the pyrazole moiety made the Sonogashira cross-coupling reaction challenging. Additionally, the selection of the ancillary ligand XPhos was essential and indispensable for the desired heterocyclic construction.