Regioselective synthesis of fluoroalkylated [1,2,3]-triazoles by Huisgen cycloaddition

Abstract

A series of fluoroalkylated 1,4-disubstituted [1,2,3]-triazoles were synthesized by the 1,3-dipolar cycloaddition of fluoroalkylated azides with terminal alkynes in the presence of Cu(I) salt as catalyst at room temperature. All the reactions were performed in highly regioselective with 1,4-disubstituted, no 1,5-disubstituted product was formed. For aryl or alkyl-alkyne, triethylamine should be used as ligand. But for propiolic ester(amide), triethylamine couldn’t be used, otherwise no products was formed. A mechanism of Cu(I) inserting the internal alkyne was suggested.