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L-Phenylalanine derived tripodal vanadium complexes as catalysts for the asymmetric reductive coupling of benzaldehyde

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dc.contributor.authorTeixeira, Carlos M.
dc.contributor.authorAdão, Pedro
dc.contributor.authorCarvalho, M. Fernanda N.N.
dc.contributor.authorGomes, Clara S.B.
dc.contributor.authorPessoa, João Costa
dc.date.accessioned2020-08-19T13:07:42Z
dc.date.available2020-08-19T13:07:42Z
dc.date.issued2020
dc.descriptionAcknowledgements The authors of Centro de Química Estrutural acknowledge the financial support of Fundação para a Ciência e a Tecnologia (UIDB/ 0100/2020), the IST-UL Centers of the Portuguese NMR and Mass Spectrometry Networks (REM2013, RNNMR), RECI/QEQ-QIN/0189/ 2012, RECI/QEQ-MED/0330/2012, grants SFRH/BPD/79778/2011, BL/CQE-2014-001 and PD/BD/106078/2015. The authors also acknowledge Dr. Maria da Conceição Oliveira and MSc. Ana Dias for the ESI mass spectrometry experiments carried out. Pedro Adão acknowledges the MARE– Marine and Environmental Sciences Centre, Polytechnic of Leiria, which is financed by national funds from FCT/ MCTES (UID/MAR/04292/2019, UIDB/04292/2020) and the project “SmartBioR- Smart Valorization of Endogenous Marine Biological Resources Under a Changing Climate” (Centro-01-0145-FEDER000018) co-funded by Centro 2020, Portugal 2020 and European Regional Development Fund (FEDER). Clara S. B. Gomes acknowledges the Associate Laboratory for Green Chemistry– LAQV and the Applied Molecular Biosciences UnitUCIBIO, which are financed by national funds from Fundação para a Ciência e a Tecnologia (UIDB/50006/2020 and UIDB/04378/2020, respectively).
dc.description.abstractTwo tripodal vanadium complexes derived from modified L-phenylalanine were prepared and characterised. Both compounds were tested for their catalytic activity in the reductive coupling of benzaldehyde. Overall, the complexes are capable of catalysing the reductive coupling of benzaldehyde in the presence of metallic zinc as co-reductant and alkylammonium or alkylpyridinium acetate salts in ethanol under mild aerobic conditions. While benzyl alcohol is generally the major product, the yield of hydrobenzoin reaches ca. 38% under these conditions. Enantioselectivities reach 39% and there is a preferential formation of the trans diastereoisomer of hydrobenzoin. Attempts to study some aspects of the underlying mechanism were made. It was found that metallic zinc is capable of reducing the complexes to VIII species, which are likely to be the active catalytic species. The methodology described may set up a basis for the development of catalytic systems for the asymmetric synthesis of hydrobenzoins under mild conditions, not requiring chlorosilanes as electrophilic reagents for the regeneration of the catalyst.pt_PT
dc.description.versioninfo:eu-repo/semantics/publishedVersionpt_PT
dc.identifier.citationTeixeira, C., Adão, P., Carvalho, M., Gomes, C., & Pessoa, J. (2020) .L-Phenylalanine derived tripodal vanadium complexes as catalysts for the asymmetric reductive coupling of benzaldehyde. Inorganica Chimica Acta. DOI: 10.1016/j.ica.2020.119727pt_PT
dc.identifier.doi10.1016/j.ica.2020.119727pt_PT
dc.identifier.issn0020-1693
dc.identifier.urihttp://hdl.handle.net/10400.8/5100
dc.language.isoengpt_PT
dc.peerreviewedyespt_PT
dc.publisherElsevierpt_PT
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.relationMarine and Environmental Sciences Centre
dc.relationAssociated Laboratory for Green Chemistry - Clean Technologies and Processes
dc.relationApplied Molecular Biosciences Unit
dc.rights.urihttp://creativecommons.org/licenses/by-nc-nd/4.0/pt_PT
dc.subjectVanadiumpt_PT
dc.subjectPinacol couplingpt_PT
dc.subjectModified phenylalaninept_PT
dc.subjectBenzaldehydept_PT
dc.subjectAsymmetric catalysispt_PT
dc.titleL-Phenylalanine derived tripodal vanadium complexes as catalysts for the asymmetric reductive coupling of benzaldehydept_PT
dc.typejournal article
dspace.entity.typePublication
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.awardTitleMarine and Environmental Sciences Centre
oaire.awardTitleAssociated Laboratory for Green Chemistry - Clean Technologies and Processes
oaire.awardTitleApplied Molecular Biosciences Unit
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/3599-PPCDT/RECI%2FQEQ-MED%2F0330%2F2012/PT
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oaire.awardURIinfo:eu-repo/grantAgreement/FCT/6817 - DCRRNI ID/UIDB%2F04292%2F2020/PT
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oaire.awardURIinfo:eu-repo/grantAgreement/FCT/6817 - DCRRNI ID/UIDB%2F04378%2F2020/PT
oaire.citation.titleInorganica Chimica Actapt_PT
oaire.citation.volume510pt_PT
oaire.fundingStream3599-PPCDT
oaire.fundingStream6817 - DCRRNI ID
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person.familyNameAdão
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rcaap.rightsclosedAccesspt_PT
rcaap.typearticlept_PT
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