In this paper, an efficient synthesis of 5-alkynyl-1,2,3-triazoles through a one-pot aerobic oxidative coupling reaction of various alkynes and azides has been developed. Further derivatization of 5-alkynyl-1,2,3-triazoles readily yielded 5-carbonyl-1,2,3-triazoles, 5-carboxylic-1,2,3-triazole, 5-hydroxyalkyl-1,2,3-triazoles and 5-quinoxaline-1,2,3-triazole, which provided an entry into structurally diverse 5-functionalized-1,2,3-triazoles.In this paper, we report a simple method for the synthesis of 5-alkynyl-1,2,3-triazoles from various alkynes and azides. The transformation of 5-alkynyl-1,2,3-triazoles to structurally diverse 5-functionalized-1,2,3-triazoles via oxidation, reduction and condensation reactions was explored.

An effective synthetic protocol for 5-halo-1,2,3-triazoles was developed by novel TBDMSCl (tert-butyldimethylsilyl chloride)-activated aerobic oxidative halogenations in this Letter. TBDMSCl, for the first time, was found to activate aerobic oxidation of CuX to produce X2 with Cu+ which then could effectively promote one-pot syntheses of 5-halo-1,2,3-triazole from alkyne, azide, and CuX (X = I, Br) under O2 atmosphere at room temperature. The advantages in this method include inexpensive and green O2 as oxidant, use of mild and non-oxidative additive, and wide scope of substrates.An effective three-component assembly of 5-halo-1,2,3-triazoles from alkyne, azide, and CuX was developed by a novel TBDMSCl-activated aerobic oxidative halogenation in this Letter.