Heterogeneous Gold Nanoparticle-Based Catalysts for the Synthesis of Click-Derived Triazoles via the Azide-Alkyne Cycloaddition Reaction
Autor(a) principal: | |
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Data de Publicação: | 2021 |
Outros Autores: | , , , , , |
Tipo de documento: | Artigo |
Idioma: | eng |
Título da fonte: | Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
Texto Completo: | http://hdl.handle.net/10316/103213 https://doi.org/10.3390/catal12010045 |
Resumo: | A supported gold nanoparticle-catalyzed strategy has been utilized to promote a click chemistry reaction for the synthesis of 1,2,3-triazoles via the azide-alkyne cycloaddition (AAC) reaction. While the advent of effective non-copper catalysts (i.e., Ru, Ag, Ir) has demonstrated the catalysis of the AAC reaction, additional robust catalytic systems complementary to the copper catalyzed AAC remain in high demand. Herein, Au nanoparticles supported on Al2O3, Fe2O3, TiO2 and ZnO, along with gold reference catalysts (gold on carbon and gold on titania supplied by theWorld Gold Council) were used as catalysts for the AAC reaction. The supported Au nanoparticles with metal loadings of 0.7–1.6% (w/w relative to support) were able to selectively obtain 1,4-disubstituted-1,2,3-triazoles in moderate yields up to 79% after 15 min, under microwave irradiation at 150 C using a 0.5–1.0 mol% catalyst loading through a one-pot three-component (terminal alkyne, organohalide and sodium azide) procedure according to the “click” rules. Among the supported Au catalysts, Au/TiO2 gave the best results. |
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Heterogeneous Gold Nanoparticle-Based Catalysts for the Synthesis of Click-Derived Triazoles via the Azide-Alkyne Cycloaddition ReactionAu nanoparticlessupported catalystsazide-alkyne; 1,2,3-triazolesA supported gold nanoparticle-catalyzed strategy has been utilized to promote a click chemistry reaction for the synthesis of 1,2,3-triazoles via the azide-alkyne cycloaddition (AAC) reaction. While the advent of effective non-copper catalysts (i.e., Ru, Ag, Ir) has demonstrated the catalysis of the AAC reaction, additional robust catalytic systems complementary to the copper catalyzed AAC remain in high demand. Herein, Au nanoparticles supported on Al2O3, Fe2O3, TiO2 and ZnO, along with gold reference catalysts (gold on carbon and gold on titania supplied by theWorld Gold Council) were used as catalysts for the AAC reaction. The supported Au nanoparticles with metal loadings of 0.7–1.6% (w/w relative to support) were able to selectively obtain 1,4-disubstituted-1,2,3-triazoles in moderate yields up to 79% after 15 min, under microwave irradiation at 150 C using a 0.5–1.0 mol% catalyst loading through a one-pot three-component (terminal alkyne, organohalide and sodium azide) procedure according to the “click” rules. Among the supported Au catalysts, Au/TiO2 gave the best results.2021info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articlehttp://hdl.handle.net/10316/103213http://hdl.handle.net/10316/103213https://doi.org/10.3390/catal12010045eng2073-4344Librando, Ivy L.Mahmoud, Abdallah G.Carabineiro, Sónia A. C.Guedes da Silva, M. Fátima C.Maldonado-Hódar, Francisco J.Geraldes, Carlos F. G. C.Pombeiro, Armando J. L.info:eu-repo/semantics/openAccessreponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãoinstacron:RCAAP2022-10-24T20:32:36Zoai:estudogeral.uc.pt:10316/103213Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-19T21:20:05.222467Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãofalse |
dc.title.none.fl_str_mv |
Heterogeneous Gold Nanoparticle-Based Catalysts for the Synthesis of Click-Derived Triazoles via the Azide-Alkyne Cycloaddition Reaction |
title |
Heterogeneous Gold Nanoparticle-Based Catalysts for the Synthesis of Click-Derived Triazoles via the Azide-Alkyne Cycloaddition Reaction |
spellingShingle |
Heterogeneous Gold Nanoparticle-Based Catalysts for the Synthesis of Click-Derived Triazoles via the Azide-Alkyne Cycloaddition Reaction Librando, Ivy L. Au nanoparticles supported catalysts azide-alkyne; 1,2,3-triazoles |
title_short |
Heterogeneous Gold Nanoparticle-Based Catalysts for the Synthesis of Click-Derived Triazoles via the Azide-Alkyne Cycloaddition Reaction |
title_full |
Heterogeneous Gold Nanoparticle-Based Catalysts for the Synthesis of Click-Derived Triazoles via the Azide-Alkyne Cycloaddition Reaction |
title_fullStr |
Heterogeneous Gold Nanoparticle-Based Catalysts for the Synthesis of Click-Derived Triazoles via the Azide-Alkyne Cycloaddition Reaction |
title_full_unstemmed |
Heterogeneous Gold Nanoparticle-Based Catalysts for the Synthesis of Click-Derived Triazoles via the Azide-Alkyne Cycloaddition Reaction |
title_sort |
Heterogeneous Gold Nanoparticle-Based Catalysts for the Synthesis of Click-Derived Triazoles via the Azide-Alkyne Cycloaddition Reaction |
author |
Librando, Ivy L. |
author_facet |
Librando, Ivy L. Mahmoud, Abdallah G. Carabineiro, Sónia A. C. Guedes da Silva, M. Fátima C. Maldonado-Hódar, Francisco J. Geraldes, Carlos F. G. C. Pombeiro, Armando J. L. |
author_role |
author |
author2 |
Mahmoud, Abdallah G. Carabineiro, Sónia A. C. Guedes da Silva, M. Fátima C. Maldonado-Hódar, Francisco J. Geraldes, Carlos F. G. C. Pombeiro, Armando J. L. |
author2_role |
author author author author author author |
dc.contributor.author.fl_str_mv |
Librando, Ivy L. Mahmoud, Abdallah G. Carabineiro, Sónia A. C. Guedes da Silva, M. Fátima C. Maldonado-Hódar, Francisco J. Geraldes, Carlos F. G. C. Pombeiro, Armando J. L. |
dc.subject.por.fl_str_mv |
Au nanoparticles supported catalysts azide-alkyne; 1,2,3-triazoles |
topic |
Au nanoparticles supported catalysts azide-alkyne; 1,2,3-triazoles |
description |
A supported gold nanoparticle-catalyzed strategy has been utilized to promote a click chemistry reaction for the synthesis of 1,2,3-triazoles via the azide-alkyne cycloaddition (AAC) reaction. While the advent of effective non-copper catalysts (i.e., Ru, Ag, Ir) has demonstrated the catalysis of the AAC reaction, additional robust catalytic systems complementary to the copper catalyzed AAC remain in high demand. Herein, Au nanoparticles supported on Al2O3, Fe2O3, TiO2 and ZnO, along with gold reference catalysts (gold on carbon and gold on titania supplied by theWorld Gold Council) were used as catalysts for the AAC reaction. The supported Au nanoparticles with metal loadings of 0.7–1.6% (w/w relative to support) were able to selectively obtain 1,4-disubstituted-1,2,3-triazoles in moderate yields up to 79% after 15 min, under microwave irradiation at 150 C using a 0.5–1.0 mol% catalyst loading through a one-pot three-component (terminal alkyne, organohalide and sodium azide) procedure according to the “click” rules. Among the supported Au catalysts, Au/TiO2 gave the best results. |
publishDate |
2021 |
dc.date.none.fl_str_mv |
2021 |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/article |
format |
article |
status_str |
publishedVersion |
dc.identifier.uri.fl_str_mv |
http://hdl.handle.net/10316/103213 http://hdl.handle.net/10316/103213 https://doi.org/10.3390/catal12010045 |
url |
http://hdl.handle.net/10316/103213 https://doi.org/10.3390/catal12010045 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
2073-4344 |
dc.rights.driver.fl_str_mv |
info:eu-repo/semantics/openAccess |
eu_rights_str_mv |
openAccess |
dc.source.none.fl_str_mv |
reponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação instacron:RCAAP |
instname_str |
Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação |
instacron_str |
RCAAP |
institution |
RCAAP |
reponame_str |
Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
collection |
Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
repository.name.fl_str_mv |
Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação |
repository.mail.fl_str_mv |
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1799134094481686528 |