Copper nanoparticle catalyzed regioselective cycloaddition of terminal acetylenes to sodium azide in the presence of O-tosyl fluorocarbohydrate derivatives: assembly of novel enantiopure fluoromonosaccharides with 1,2,3-triazole and 4-phenyl-oxazolidin-2-one subunits

Abstract

A three-component reaction of O-tosyl carbohydrate derivatives with sodium azide and terminal alkynes can be catalyzed by copper nanoparticles under ambient conditions. A series of 1,4-disubstituted-1,2,3-triazoles were obtained regioselectively by this one-pot strategy in good to excellent yields (70-90%). The salient features of the present protocol are mild reaction conditions, a shorter reaction time, and its applicability to a wide range of substrates.

Keywords

• carbohydrates
• terminal alkyne
• copper nanoparticles
• cycloaddition
• 1,2,3-triazoles