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

Ahlem Guesmi, Naoufel Ben Hamadi

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

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DOI: http://dx.doi.org/10.20450/mjcce.2016.758

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