Abstract
The copper(I)-catalyzed azide−alkyne cycloaddition (CuAAC) reaction is considered to be the most representative ligation process within the context of the “click chemistry” concept. This CuAAC reaction, which yields compounds containing a 1,2,3-triazole core, has become relevant in the construction of biologically complex systems, bioconjugation strategies, and supramolecular and material sciences. Although many CuAAC reactions are performed under homogenous conditions, heterogenous copper-based catalytic systems are gaining exponential interest, relying on the easy removal, recovery, and reusability of catalytically copper species. The present review covers the most recently developed copper-containing heterogenous solid catalytic systems that use solid inorganic/organic hybrid supports, and which have been used in promoting CuAAC reactions. Due to the demand for 1,2,3-triazoles as non-classical bioisosteres and as framework-based drugs, the CuAAC reaction promoted by solid heterogenous catalysts has greatly improved the recovery and removal of copper species, usually by simple filtration. In so doing, the solving of the toxicity issue regarding copper particles in compounds of biological interest has been achieved. This protocol is also expected to produce a practical chemical process for accessing such compounds on an industrial scale.
Highlights
Introduction“Click chemistry” is a concept that uses the most convenient and practical chemical transformations for clicking available reagents or building blocks into final products with high yield and in a selective manner [1]
Laboratoire de Chimie Analytique et Moléculaire/LCAM, Faculté Polydisciplinaire de Safi, Laboratoire de Chimie de Coordination et d’Analytique/LCCA, Département de Chimie, Faculté des Sciences d’El Jadida, Université Chouaïb Doukkali, El Jadida 24000, Morocco
The present review provides an up-to-date overview of the covalent and non-covalent immobilization methods of copper salts on inorganic solid supports as well as carbon and magnetic materials applied in azide–alkyne [3+2]
Summary
“Click chemistry” is a concept that uses the most convenient and practical chemical transformations for clicking available reagents or building blocks into final products with high yield and in a selective manner [1]. Since the independent discovery of CuAAC by Sharpless et al [3] and Meldal et al [4], several other research groups have reported an improved version of the Huisgen [3+2] cycloaddition by using a copper(I) catalyst to exclusively produce the corresponding 1,4-disubstituted 1,2,3-triazoles in very high yields with few or no side products. Due to these characteristics, copper-catalyzed azide–alkyne [3+2] cycloaddition (CuAAC) has become a leading method for the covalent assembly of large and small molecules by using 1,2,3-triazole as a bridging block unit [5,6].
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