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Cu(II) complexes derived from N-carboxymethyl and N-carboxyethyl amino acids as catalysts for asymmetric oxidative coupling of 2-naphthol

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dc.contributor.authorAdão, Pedro
dc.contributor.authorTeixeira, Carlos M.
dc.contributor.authorCarvalho, M. Fernanda N.N.
dc.contributor.authorKuznetsov, Maxim L.
dc.contributor.authorGomes, Clara S.B.
dc.contributor.authorPessoa, João Costa
dc.date.accessioned2020-07-16T10:57:47Z
dc.date.available2020-07-16T10:57:47Z
dc.date.issued2019
dc.descriptionThis 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/QEQMED/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).pt_PT
dc.description.abstractThe 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.pt_PT
dc.description.versioninfo:eu-repo/semantics/publishedVersionpt_PT
dc.identifier.citationAdão, P., Teixeira, C. M., Carvalho, M. F. N. N., Kuznetsov, M. L., Gomes, C. S. B., & Pessoa, J. C. (2019). Cu(II) complexes derived from N-carboxymethyl and N-carboxyethyl amino acids as catalysts for asymmetric oxidative coupling of 2-naphthol. Molecular Catalysis, 475, [110480]. https://doi.org/10.1016/j.mcat.2019.110480pt_PT
dc.identifier.doioi.org/10.1016/j.mcat.2019.110480pt_PT
dc.identifier.issn2468-8231
dc.identifier.urihttp://hdl.handle.net/10400.8/5012
dc.language.isoengpt_PT
dc.peerreviewedyespt_PT
dc.publisherElsevierpt_PT
dc.relationNovos Materiais Organometálicos Luminescentes: Preparação, Propriedades Fotofísicas e Aplicações em Díodos Emissores de Luz de Elevada Eficiência
dc.relationDEVELOPMENT OF NEW RECYCLABLE AND WIDELY APPLICABLE HETEROGENEOUS CATALYSTS FOR CATALYTIC OXIDATIONS AND REDUCTIONS
dc.relationAminoacid-derived transition metal complexes as C-C bond forming and C-H activation catalysts
dc.relationMARE - Marine and Environmental Sciences Centre
dc.relationAssociated Laboratory for Green Chemistry - Clean Technologies and Processes
dc.rights.urihttp://creativecommons.org/licenses/by-nc-nd/4.0/pt_PT
dc.subjectAmino acidpt_PT
dc.subjectCopperpt_PT
dc.subject2-Naphtholpt_PT
dc.subjectOxidative couplingpt_PT
dc.subjectAsymmetric catalysispt_PT
dc.titleCu(II) complexes derived from N-carboxymethyl and N-carboxyethyl amino acids as catalysts for asymmetric oxidative coupling of 2-naphtholpt_PT
dc.typejournal article
dspace.entity.typePublication
oaire.awardTitleNovos Materiais Organometálicos Luminescentes: Preparação, Propriedades Fotofísicas e Aplicações em Díodos Emissores de Luz de Elevada Eficiência
oaire.awardTitleDEVELOPMENT OF NEW RECYCLABLE AND WIDELY APPLICABLE HETEROGENEOUS CATALYSTS FOR CATALYTIC OXIDATIONS AND REDUCTIONS
oaire.awardTitleAminoacid-derived transition metal complexes as C-C bond forming and C-H activation catalysts
oaire.awardTitleMARE - Marine and Environmental Sciences Centre
oaire.awardTitleAssociated Laboratory for Green Chemistry - Clean Technologies and Processes
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/3599-PPCDT/RECI%2FQEQ-QIN%2F0189%2F2012/PT
oaire.awardURIinfo:eu-repo/grantAgreement/FCT//SFRH%2FBPD%2F107834%2F2015/PT
oaire.awardURIinfo:eu-repo/grantAgreement/FCT//SFRH%2FBPD%2F79778%2F2011/PT
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oaire.awardURIinfo:eu-repo/grantAgreement/FCT/6817 - DCRRNI ID/UID%2FMAR%2F04292%2F2019/PT
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/6817 - DCRRNI ID/UID%2FQUI%2F50006%2F2019/PT
oaire.citation.titleMolecular Catalysispt_PT
oaire.citation.volume475pt_PT
oaire.fundingStream3599-PPCDT
oaire.fundingStream6817 - DCRRNI ID
oaire.fundingStream6817 - DCRRNI ID
person.familyNameAdão
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