Cargando…

Recent Advances in Copper-Based Solid Heterogeneous Catalysts for Azide–Alkyne Cycloaddition Reactions

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...

Descripción completa

Detalles Bibliográficos
Autores principales: Aflak, Noura, Ben El Ayouchia, Hicham, Bahsis, Lahoucine, Anane, Hafid, Julve, Miguel, Stiriba, Salah-Eddine
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8874673/
https://www.ncbi.nlm.nih.gov/pubmed/35216495
http://dx.doi.org/10.3390/ijms23042383
_version_ 1784657745216012288
author Aflak, Noura
Ben El Ayouchia, Hicham
Bahsis, Lahoucine
Anane, Hafid
Julve, Miguel
Stiriba, Salah-Eddine
author_facet Aflak, Noura
Ben El Ayouchia, Hicham
Bahsis, Lahoucine
Anane, Hafid
Julve, Miguel
Stiriba, Salah-Eddine
author_sort Aflak, Noura
collection PubMed
description 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.
format Online
Article
Text
id pubmed-8874673
institution National Center for Biotechnology Information
language English
publishDate 2022
publisher MDPI
record_format MEDLINE/PubMed
spelling pubmed-88746732022-02-26 Recent Advances in Copper-Based Solid Heterogeneous Catalysts for Azide–Alkyne Cycloaddition Reactions Aflak, Noura Ben El Ayouchia, Hicham Bahsis, Lahoucine Anane, Hafid Julve, Miguel Stiriba, Salah-Eddine Int J Mol Sci Review 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. MDPI 2022-02-21 /pmc/articles/PMC8874673/ /pubmed/35216495 http://dx.doi.org/10.3390/ijms23042383 Text en © 2022 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Review
Aflak, Noura
Ben El Ayouchia, Hicham
Bahsis, Lahoucine
Anane, Hafid
Julve, Miguel
Stiriba, Salah-Eddine
Recent Advances in Copper-Based Solid Heterogeneous Catalysts for Azide–Alkyne Cycloaddition Reactions
title Recent Advances in Copper-Based Solid Heterogeneous Catalysts for Azide–Alkyne Cycloaddition Reactions
title_full Recent Advances in Copper-Based Solid Heterogeneous Catalysts for Azide–Alkyne Cycloaddition Reactions
title_fullStr Recent Advances in Copper-Based Solid Heterogeneous Catalysts for Azide–Alkyne Cycloaddition Reactions
title_full_unstemmed Recent Advances in Copper-Based Solid Heterogeneous Catalysts for Azide–Alkyne Cycloaddition Reactions
title_short Recent Advances in Copper-Based Solid Heterogeneous Catalysts for Azide–Alkyne Cycloaddition Reactions
title_sort recent advances in copper-based solid heterogeneous catalysts for azide–alkyne cycloaddition reactions
topic Review
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8874673/
https://www.ncbi.nlm.nih.gov/pubmed/35216495
http://dx.doi.org/10.3390/ijms23042383
work_keys_str_mv AT aflaknoura recentadvancesincopperbasedsolidheterogeneouscatalystsforazidealkynecycloadditionreactions
AT benelayouchiahicham recentadvancesincopperbasedsolidheterogeneouscatalystsforazidealkynecycloadditionreactions
AT bahsislahoucine recentadvancesincopperbasedsolidheterogeneouscatalystsforazidealkynecycloadditionreactions
AT ananehafid recentadvancesincopperbasedsolidheterogeneouscatalystsforazidealkynecycloadditionreactions
AT julvemiguel recentadvancesincopperbasedsolidheterogeneouscatalystsforazidealkynecycloadditionreactions
AT stiribasalaheddine recentadvancesincopperbasedsolidheterogeneouscatalystsforazidealkynecycloadditionreactions