Cargando…

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...

Descripción completa

Detalles Bibliográficos
Autores principales: Aflak, Noura, Ben El Ayouchia, Hicham, Bahsis, Lahoucine, El Mouchtari, El Mountassir, Julve, Miguel, Rafqah, Salah, Anane, Hafid, Stiriba, Salah-Eddine
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Frontiers Media S.A. 2019
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
_version_ 1783397967748661248
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
work_keys_str_mv AT aflaknoura sustainableconstructionofheterocyclic123triazolesbystrictclick32cycloadditionreactionsbetweenazidesandalkynesoncoppercarboninwater
AT benelayouchiahicham sustainableconstructionofheterocyclic123triazolesbystrictclick32cycloadditionreactionsbetweenazidesandalkynesoncoppercarboninwater
AT bahsislahoucine sustainableconstructionofheterocyclic123triazolesbystrictclick32cycloadditionreactionsbetweenazidesandalkynesoncoppercarboninwater
AT elmouchtarielmountassir sustainableconstructionofheterocyclic123triazolesbystrictclick32cycloadditionreactionsbetweenazidesandalkynesoncoppercarboninwater
AT julvemiguel sustainableconstructionofheterocyclic123triazolesbystrictclick32cycloadditionreactionsbetweenazidesandalkynesoncoppercarboninwater
AT rafqahsalah sustainableconstructionofheterocyclic123triazolesbystrictclick32cycloadditionreactionsbetweenazidesandalkynesoncoppercarboninwater
AT ananehafid sustainableconstructionofheterocyclic123triazolesbystrictclick32cycloadditionreactionsbetweenazidesandalkynesoncoppercarboninwater
AT stiribasalaheddine sustainableconstructionofheterocyclic123triazolesbystrictclick32cycloadditionreactionsbetweenazidesandalkynesoncoppercarboninwater