Synthesis of a novel series of Cu(I) complexes bearing alkylated 1,3,5-triaza-7-phosphaadamantane as homogeneous and carbon-supported catalysts for the synthesis of 1-and 2-substituted-1,2,3-triazoles

Detalhes bibliográficos
Autor(a) principal: Librando, Ivy L.
Data de Publicação: 2021
Outros Autores: Mahmoud, Abdallah G., Carabineiro, Sónia A. C., Guedes da Silva, M. Fátima C., Geraldes, Carlos F. G. C., Pombeiro, Armando J. L.
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
Texto Completo: http://hdl.handle.net/10362/131845
Resumo: PD/BD 135555/2018 CO2usE-1801P.00867.1.01 (contract no. IST-ID/263/2019)
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spelling Synthesis of a novel series of Cu(I) complexes bearing alkylated 1,3,5-triaza-7-phosphaadamantane as homogeneous and carbon-supported catalysts for the synthesis of 1-and 2-substituted-1,2,3-triazolesAzide-Alkyne cycloadditionCarbon nanotubesClick chemistryCopper complexesP-ligandsPTASupported catalysisChemical Engineering(all)Materials Science(all)PD/BD 135555/2018 CO2usE-1801P.00867.1.01 (contract no. IST-ID/263/2019)The N-alkylation of 1,3,5-triaza-7-phosphaadamantane (PTA) with ortho-, meta-and para-substituted nitrobenzyl bromide under mild conditions afforded three hydrophilic PTA ammonium salts, which were used to obtain a new set of seven water-soluble copper(I) complexes. The new compounds were fully characterized and their catalytic activity was investigated for the low power microwave assisted one-pot azide–alkyne cycloaddition reaction in homogeneous aqueous medium to obtain disubstituted 1,2,3-triazoles. The most active catalysts were immobilized on activated carbon (AC), multi-walled carbon nanotubes (CNT), as well as surface functionalized AC and CNT, with the most efficient support being the CNT treated with nitric acid and NaOH. In the presence of the immobilized catalyst, several 1,4-disubstituted-1,2,3-triazoles were obtained from the reaction of terminal alkynes, organic halides and sodium azide in moderate yields up to 80%. Furthermore, the catalyzed reaction of terminal alkynes, formaldehyde and sodium azide afforded 2-hydroxymethyl-2H-1,2,3-triazoles in high yields up to 99%. The immobilized catalyst can be recovered and recycled through simple workup steps and reused up to five consecutive cycles without a marked loss in activity. The described catalytic systems proceed with a broad substrate scope, under microwave irradiation in aqueous medium and according to “click rules”.LAQV@REQUIMTEDQ - Departamento de QuímicaRUNLibrando, Ivy L.Mahmoud, Abdallah G.Carabineiro, Sónia A. C.Guedes da Silva, M. Fátima C.Geraldes, Carlos F. G. C.Pombeiro, Armando J. L.2022-01-29T06:03:42Z2021-10-132021-10-13T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/10362/131845eng2079-4991PURE: 34511189https://doi.org/10.3390/nano11102702info: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:RCAAP2024-03-11T05:10:32Zoai:run.unl.pt:10362/131845Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-20T03:47:17.028278Repositório 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 Synthesis of a novel series of Cu(I) complexes bearing alkylated 1,3,5-triaza-7-phosphaadamantane as homogeneous and carbon-supported catalysts for the synthesis of 1-and 2-substituted-1,2,3-triazoles
title Synthesis of a novel series of Cu(I) complexes bearing alkylated 1,3,5-triaza-7-phosphaadamantane as homogeneous and carbon-supported catalysts for the synthesis of 1-and 2-substituted-1,2,3-triazoles
spellingShingle Synthesis of a novel series of Cu(I) complexes bearing alkylated 1,3,5-triaza-7-phosphaadamantane as homogeneous and carbon-supported catalysts for the synthesis of 1-and 2-substituted-1,2,3-triazoles
Librando, Ivy L.
Azide-Alkyne cycloaddition
Carbon nanotubes
Click chemistry
Copper complexes
P-ligands
PTA
Supported catalysis
Chemical Engineering(all)
Materials Science(all)
title_short Synthesis of a novel series of Cu(I) complexes bearing alkylated 1,3,5-triaza-7-phosphaadamantane as homogeneous and carbon-supported catalysts for the synthesis of 1-and 2-substituted-1,2,3-triazoles
title_full Synthesis of a novel series of Cu(I) complexes bearing alkylated 1,3,5-triaza-7-phosphaadamantane as homogeneous and carbon-supported catalysts for the synthesis of 1-and 2-substituted-1,2,3-triazoles
title_fullStr Synthesis of a novel series of Cu(I) complexes bearing alkylated 1,3,5-triaza-7-phosphaadamantane as homogeneous and carbon-supported catalysts for the synthesis of 1-and 2-substituted-1,2,3-triazoles
title_full_unstemmed Synthesis of a novel series of Cu(I) complexes bearing alkylated 1,3,5-triaza-7-phosphaadamantane as homogeneous and carbon-supported catalysts for the synthesis of 1-and 2-substituted-1,2,3-triazoles
title_sort Synthesis of a novel series of Cu(I) complexes bearing alkylated 1,3,5-triaza-7-phosphaadamantane as homogeneous and carbon-supported catalysts for the synthesis of 1-and 2-substituted-1,2,3-triazoles
author Librando, Ivy L.
author_facet Librando, Ivy L.
Mahmoud, Abdallah G.
Carabineiro, Sónia A. C.
Guedes da Silva, M. Fátima C.
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.
Geraldes, Carlos F. G. C.
Pombeiro, Armando J. L.
author2_role author
author
author
author
author
dc.contributor.none.fl_str_mv LAQV@REQUIMTE
DQ - Departamento de Química
RUN
dc.contributor.author.fl_str_mv Librando, Ivy L.
Mahmoud, Abdallah G.
Carabineiro, Sónia A. C.
Guedes da Silva, M. Fátima C.
Geraldes, Carlos F. G. C.
Pombeiro, Armando J. L.
dc.subject.por.fl_str_mv Azide-Alkyne cycloaddition
Carbon nanotubes
Click chemistry
Copper complexes
P-ligands
PTA
Supported catalysis
Chemical Engineering(all)
Materials Science(all)
topic Azide-Alkyne cycloaddition
Carbon nanotubes
Click chemistry
Copper complexes
P-ligands
PTA
Supported catalysis
Chemical Engineering(all)
Materials Science(all)
description PD/BD 135555/2018 CO2usE-1801P.00867.1.01 (contract no. IST-ID/263/2019)
publishDate 2021
dc.date.none.fl_str_mv 2021-10-13
2021-10-13T00:00:00Z
2022-01-29T06:03:42Z
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/10362/131845
url http://hdl.handle.net/10362/131845
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv 2079-4991
PURE: 34511189
https://doi.org/10.3390/nano11102702
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
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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