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

Bibliographic Details
Main Author: Adão, P.
Publication Date: 2019
Other Authors: Teixeira, Carlos M., Carvalho, M. Fernanda N. N., Kuznetsov, Maxim L., Gomes, Clara S.B., Pessoa, João Costa
Format: Article
Language: eng
Source: Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
Download full: https://doi.org/10.1016/j.mcat.2019.110480
Summary: 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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spelling 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
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)
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instacron:RCAAP
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instacron_str RCAAP
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collection Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
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