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Sustainable Construction of Heterocyclic 1,2,3-Triazoles by Strict Click [3+2] Cycloaddition Reactions Between Azides and Alkynes on Copper/Carbon in Water
1,4-Disubstituted-1,2,3-triazoles, considered as an important and useful class of heterocycles with potential applications in material science and biology, have been prepared in an efficient and selective manner by copper on carbon-catalyzed [3+2] cycloaddition reactions of azides and alkynes (CuAAC...
Autores principales: | , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Frontiers Media S.A.
2019
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6389623/ https://www.ncbi.nlm.nih.gov/pubmed/30838201 http://dx.doi.org/10.3389/fchem.2019.00081 |
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author | Aflak, Noura Ben El Ayouchia, Hicham Bahsis, Lahoucine El Mouchtari, El Mountassir Julve, Miguel Rafqah, Salah Anane, Hafid Stiriba, Salah-Eddine |
author_facet | Aflak, Noura Ben El Ayouchia, Hicham Bahsis, Lahoucine El Mouchtari, El Mountassir Julve, Miguel Rafqah, Salah Anane, Hafid Stiriba, Salah-Eddine |
author_sort | Aflak, Noura |
collection | PubMed |
description | 1,4-Disubstituted-1,2,3-triazoles, considered as an important and useful class of heterocycles with potential applications in material science and biology, have been prepared in an efficient and selective manner by copper on carbon-catalyzed [3+2] cycloaddition reactions of azides and alkynes (CuAAC) in water under strict click chemistry conditions. Copper(I) catalysts heterogenized onto commercially activated carbon materials (Cu-CC) and on another carbon material produced from vegetable biomass using Argan nut shells (Cu-CANS) were found to be versatile catalytic sources for sustainable CuAAC. These copper on carbon supports were prepared and fully characterized by using two types of activated carbons that exhibit different porosity and specific surface. The delineation of the nature of the catalytic copper species and the role of the carbon support in the CuAAC were addressed. These heterogeneous copper on carbon catalysts were recovered and reused until ten catalytic runs without any noticeable loss of activity. |
format | Online Article Text |
id | pubmed-6389623 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2019 |
publisher | Frontiers Media S.A. |
record_format | MEDLINE/PubMed |
spelling | pubmed-63896232019-03-05 Sustainable Construction of Heterocyclic 1,2,3-Triazoles by Strict Click [3+2] Cycloaddition Reactions Between Azides and Alkynes on Copper/Carbon in Water Aflak, Noura Ben El Ayouchia, Hicham Bahsis, Lahoucine El Mouchtari, El Mountassir Julve, Miguel Rafqah, Salah Anane, Hafid Stiriba, Salah-Eddine Front Chem Chemistry 1,4-Disubstituted-1,2,3-triazoles, considered as an important and useful class of heterocycles with potential applications in material science and biology, have been prepared in an efficient and selective manner by copper on carbon-catalyzed [3+2] cycloaddition reactions of azides and alkynes (CuAAC) in water under strict click chemistry conditions. Copper(I) catalysts heterogenized onto commercially activated carbon materials (Cu-CC) and on another carbon material produced from vegetable biomass using Argan nut shells (Cu-CANS) were found to be versatile catalytic sources for sustainable CuAAC. These copper on carbon supports were prepared and fully characterized by using two types of activated carbons that exhibit different porosity and specific surface. The delineation of the nature of the catalytic copper species and the role of the carbon support in the CuAAC were addressed. These heterogeneous copper on carbon catalysts were recovered and reused until ten catalytic runs without any noticeable loss of activity. Frontiers Media S.A. 2019-02-19 /pmc/articles/PMC6389623/ /pubmed/30838201 http://dx.doi.org/10.3389/fchem.2019.00081 Text en Copyright © 2019 Aflak, Ben El Ayouchia, Bahsis, El Mouchtari, Julve, Rafqah, Anane and Stiriba. http://creativecommons.org/licenses/by/4.0/ This is an open-access article distributed under the terms of the Creative Commons Attribution License (CC BY). The use, distribution or reproduction in other forums is permitted, provided the original author(s) and the copyright owner(s) are credited and that the original publication in this journal is cited, in accordance with accepted academic practice. No use, distribution or reproduction is permitted which does not comply with these terms. |
spellingShingle | Chemistry Aflak, Noura Ben El Ayouchia, Hicham Bahsis, Lahoucine El Mouchtari, El Mountassir Julve, Miguel Rafqah, Salah Anane, Hafid Stiriba, Salah-Eddine Sustainable Construction of Heterocyclic 1,2,3-Triazoles by Strict Click [3+2] Cycloaddition Reactions Between Azides and Alkynes on Copper/Carbon in Water |
title | Sustainable Construction of Heterocyclic 1,2,3-Triazoles by Strict Click [3+2] Cycloaddition Reactions Between Azides and Alkynes on Copper/Carbon in Water |
title_full | Sustainable Construction of Heterocyclic 1,2,3-Triazoles by Strict Click [3+2] Cycloaddition Reactions Between Azides and Alkynes on Copper/Carbon in Water |
title_fullStr | Sustainable Construction of Heterocyclic 1,2,3-Triazoles by Strict Click [3+2] Cycloaddition Reactions Between Azides and Alkynes on Copper/Carbon in Water |
title_full_unstemmed | Sustainable Construction of Heterocyclic 1,2,3-Triazoles by Strict Click [3+2] Cycloaddition Reactions Between Azides and Alkynes on Copper/Carbon in Water |
title_short | Sustainable Construction of Heterocyclic 1,2,3-Triazoles by Strict Click [3+2] Cycloaddition Reactions Between Azides and Alkynes on Copper/Carbon in Water |
title_sort | sustainable construction of heterocyclic 1,2,3-triazoles by strict click [3+2] cycloaddition reactions between azides and alkynes on copper/carbon in water |
topic | Chemistry |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6389623/ https://www.ncbi.nlm.nih.gov/pubmed/30838201 http://dx.doi.org/10.3389/fchem.2019.00081 |
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