Azide-alkyne cycloaddition (click) reaction in biomass-derived solvent CyreneTM under one-pot conditions
Zoltán Medgyesi1, László T Mika1
1Department of Chemical and Environmental Process Engineering, Faculty of Chemical Technology and Biotechnology, Budapest University of Technology and Economics, Műegyetem rkp. 3., H-1111, Budapest, Hungary.
Abstract:
It was demonstrated that CyreneTM, as a biomass-originated polar aprotic solvent, could be utilized as an alternative reaction medium for one-pot copper(I)-catalyzed azide-alkyne cycloaddition (click or CuAAC) reactions, for the synthesis of various 1,2,3-triazoles under mild conditions. Nineteen products involving N-substituted-4-phenyl-1H-1,2,3- and 1-allyl-4-substituted-1H-1,2,3-triazoles were synthesized under one-pot conditions and isolated with good to excellent yields (50-96%) and purity (>98%). The observed results represent an example that proves that biomass-derived safer solvents can be introduced into a synthetically important transformation exhibiting higher chemical and environmental safety.
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