Cu(II) complexes derived from N-carboxymethyl and N-carboxyethyl amino acids as catalysts for asymmetric oxidative coupling of 2-naphthol
Autor(a) principal: | |
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Data de Publicação: | 2019 |
Outros Autores: | , , , , |
Tipo de documento: | Artigo |
Idioma: | eng |
Título da fonte: | Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
Texto Completo: | https://doi.org/10.1016/j.mcat.2019.110480 |
Resumo: | This work was supported by Fundação para a Ciência e a Tecnologia (FCT/MCTES) , UID/QUI/UI0100/2019 , the IST-UL Centers of the Portuguese NMR and Mass Spectrometry Networks ( REM2013 , RNNMR , SAICT nº 22125 ), RECI/QEQ-QIN/0189/2012, RECI/QEQ-MED/0330/2012, grants SFRH/BPD/107834/2015, SFRH/BPD/79778/2011 and PD/BD/106078/2015. Pedro Adão acknowledges the MARE – Marine and Environmental Sciences Centre, Instituto Politécnico de Leiria, which is financed by national funds from Fundação para a Ciência e a Tecnologia (FCT/MCTES) ( UID/MAR/04292/2019 ), the project “SmartBioR- Smart Valorization of Endogenous Marine Biological Resources Under a Changing Climate” (Centro-01-0145-FEDER-000018) co-funded by Centro 2020, Portugal 2020 and European Regional Development Fund (FEDER) and grant Centro-01-0145-FEDER-000018-BPD4. Clara S. B. Gomes acknowledges the Associate Laboratory for Green Chemistry- LAQV, which is financed by national funds from Fundação para a Ciência e a Tecnologia (FCT/MCTES) ( UID/QUI/50006/2019 ). |
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Cu(II) complexes derived from N-carboxymethyl and N-carboxyethyl amino acids as catalysts for asymmetric oxidative coupling of 2-naphthol2-NaphtholAmino acidAsymmetric catalysisCopperOxidative couplingCatalysisProcess Chemistry and TechnologyPhysical and Theoretical ChemistryThis work was supported by Fundação para a Ciência e a Tecnologia (FCT/MCTES) , UID/QUI/UI0100/2019 , the IST-UL Centers of the Portuguese NMR and Mass Spectrometry Networks ( REM2013 , RNNMR , SAICT nº 22125 ), RECI/QEQ-QIN/0189/2012, RECI/QEQ-MED/0330/2012, grants SFRH/BPD/107834/2015, SFRH/BPD/79778/2011 and PD/BD/106078/2015. Pedro Adão acknowledges the MARE – Marine and Environmental Sciences Centre, Instituto Politécnico de Leiria, which is financed by national funds from Fundação para a Ciência e a Tecnologia (FCT/MCTES) ( UID/MAR/04292/2019 ), the project “SmartBioR- Smart Valorization of Endogenous Marine Biological Resources Under a Changing Climate” (Centro-01-0145-FEDER-000018) co-funded by Centro 2020, Portugal 2020 and European Regional Development Fund (FEDER) and grant Centro-01-0145-FEDER-000018-BPD4. Clara S. B. Gomes acknowledges the Associate Laboratory for Green Chemistry- LAQV, which is financed by national funds from Fundação para a Ciência e a Tecnologia (FCT/MCTES) ( UID/QUI/50006/2019 ).The synthesis, characterization and catalytic performance of chiral Cu(II) complexes derived from N-carboxymethylated and N-carboxyethylated amino acids is reported. The ligand precursors are prepared by single step N-alkylation of the sodium salts of the appropriate chiral amino acid with either sodium chloroacetate or sodium 3-chloropropionate in water. The Cu(II) complexes are obtained upon reaction of Cu(CH3COO)2 with the aqueous or alcoholic suspension of the suitable ligand under vigorous stirring or ultrasound irradiation at room temperature. The Cu(II) compounds are characterised by EPR, UV–vis, circular dichroism and ESI-MS. The molecular structures of two of the prepared complexes are also obtained by single-crystal X-ray diffraction analysis. The catalytic activity of the complexes in the asymmetric oxidative coupling of 2-naphthol is described. All compounds exhibit moderate activity, selectivity and enantioselectivity in ethanol/water mixtures, under aerobic conditions and using potassium iodide as additive. The yields of 1,1′-bi-2-naphthol (BINOL) reached 50% under the optimal conditions, while enantiomeric excesses reached ca. 48%. The effect of variables such as ligand substituents, solvent, temperature and additives on the catalytic activity is also described. In the absence of a base, the complexes only show catalytic activity in the presence of alkali metal iodide such as KI. Details of the oxidative coupling mechanism are studied using spectroscopic and electrochemical methodologies.LAQV@REQUIMTEDQ - Departamento de QuímicaRUNAdão, P.Teixeira, Carlos M.Carvalho, M. Fernanda N. N.Kuznetsov, Maxim L.Gomes, Clara S.B.Pessoa, João Costa2019-07-29T22:41:27Z2019-10-012019-10-01T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfhttps://doi.org/10.1016/j.mcat.2019.110480eng2468-8231PURE: 14055568http://www.scopus.com/inward/record.url?scp=85068263164&partnerID=8YFLogxKhttps://doi.org/10.1016/j.mcat.2019.110480info: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:RCAAP2024-03-11T04:34:58Zoai:run.unl.pt:10362/76916Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-20T03:35:42.499944Repositório 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 |
Cu(II) complexes derived from N-carboxymethyl and N-carboxyethyl amino acids as catalysts for asymmetric oxidative coupling of 2-naphthol |
title |
Cu(II) complexes derived from N-carboxymethyl and N-carboxyethyl amino acids as catalysts for asymmetric oxidative coupling of 2-naphthol |
spellingShingle |
Cu(II) complexes derived from N-carboxymethyl and N-carboxyethyl amino acids as catalysts for asymmetric oxidative coupling of 2-naphthol Adão, P. 2-Naphthol Amino acid Asymmetric catalysis Copper Oxidative coupling Catalysis Process Chemistry and Technology Physical and Theoretical Chemistry |
title_short |
Cu(II) complexes derived from N-carboxymethyl and N-carboxyethyl amino acids as catalysts for asymmetric oxidative coupling of 2-naphthol |
title_full |
Cu(II) complexes derived from N-carboxymethyl and N-carboxyethyl amino acids as catalysts for asymmetric oxidative coupling of 2-naphthol |
title_fullStr |
Cu(II) complexes derived from N-carboxymethyl and N-carboxyethyl amino acids as catalysts for asymmetric oxidative coupling of 2-naphthol |
title_full_unstemmed |
Cu(II) complexes derived from N-carboxymethyl and N-carboxyethyl amino acids as catalysts for asymmetric oxidative coupling of 2-naphthol |
title_sort |
Cu(II) complexes derived from N-carboxymethyl and N-carboxyethyl amino acids as catalysts for asymmetric oxidative coupling of 2-naphthol |
author |
Adão, P. |
author_facet |
Adão, P. Teixeira, Carlos M. Carvalho, M. Fernanda N. N. Kuznetsov, Maxim L. Gomes, Clara S.B. Pessoa, João Costa |
author_role |
author |
author2 |
Teixeira, Carlos M. Carvalho, M. Fernanda N. N. Kuznetsov, Maxim L. Gomes, Clara S.B. Pessoa, João Costa |
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 |
Adão, P. Teixeira, Carlos M. Carvalho, M. Fernanda N. N. Kuznetsov, Maxim L. Gomes, Clara S.B. Pessoa, João Costa |
dc.subject.por.fl_str_mv |
2-Naphthol Amino acid Asymmetric catalysis Copper Oxidative coupling Catalysis Process Chemistry and Technology Physical and Theoretical Chemistry |
topic |
2-Naphthol Amino acid Asymmetric catalysis Copper Oxidative coupling Catalysis Process Chemistry and Technology Physical and Theoretical Chemistry |
description |
This work was supported by Fundação para a Ciência e a Tecnologia (FCT/MCTES) , UID/QUI/UI0100/2019 , the IST-UL Centers of the Portuguese NMR and Mass Spectrometry Networks ( REM2013 , RNNMR , SAICT nº 22125 ), RECI/QEQ-QIN/0189/2012, RECI/QEQ-MED/0330/2012, grants SFRH/BPD/107834/2015, SFRH/BPD/79778/2011 and PD/BD/106078/2015. Pedro Adão acknowledges the MARE – Marine and Environmental Sciences Centre, Instituto Politécnico de Leiria, which is financed by national funds from Fundação para a Ciência e a Tecnologia (FCT/MCTES) ( UID/MAR/04292/2019 ), the project “SmartBioR- Smart Valorization of Endogenous Marine Biological Resources Under a Changing Climate” (Centro-01-0145-FEDER-000018) co-funded by Centro 2020, Portugal 2020 and European Regional Development Fund (FEDER) and grant Centro-01-0145-FEDER-000018-BPD4. Clara S. B. Gomes acknowledges the Associate Laboratory for Green Chemistry- LAQV, which is financed by national funds from Fundação para a Ciência e a Tecnologia (FCT/MCTES) ( UID/QUI/50006/2019 ). |
publishDate |
2019 |
dc.date.none.fl_str_mv |
2019-07-29T22:41:27Z 2019-10-01 2019-10-01T00:00:00Z |
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 |
https://doi.org/10.1016/j.mcat.2019.110480 |
url |
https://doi.org/10.1016/j.mcat.2019.110480 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
2468-8231 PURE: 14055568 http://www.scopus.com/inward/record.url?scp=85068263164&partnerID=8YFLogxK https://doi.org/10.1016/j.mcat.2019.110480 |
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info:eu-repo/semantics/openAccess |
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openAccess |
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Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação |
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