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

Detalhes bibliográficos
Autor(a) principal: Teixeira, Carlos M.
Data de Publicação: 2020
Outros Autores: Adão, Pedro, Carvalho, M. Fernanda N.N., Gomes, Clara S.B., Pessoa, João Costa
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
Texto Completo: http://hdl.handle.net/10400.8/5100
Resumo: Acknowledgements 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).
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spelling L-Phenylalanine derived tripodal vanadium complexes as catalysts for the asymmetric reductive coupling of benzaldehydeVanadiumPinacol couplingModified phenylalanineBenzaldehydeAsymmetric catalysisAcknowledgements 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).Two 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.ElsevierIC-OnlineTeixeira, Carlos M.Adão, PedroCarvalho, M. Fernanda N.N.Gomes, Clara S.B.Pessoa, João Costa2020-08-19T13:07:42Z20202020-01-01T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/10400.8/5100engTeixeira, 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.2020.1197270020-169310.1016/j.ica.2020.119727metadata only accessinfo: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:RCAAP2024-01-17T15:50:38Zoai:iconline.ipleiria.pt:10400.8/5100Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-20T01:48:47.140536Repositório 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 L-Phenylalanine derived tripodal vanadium complexes as catalysts for the asymmetric reductive coupling of benzaldehyde
title L-Phenylalanine derived tripodal vanadium complexes as catalysts for the asymmetric reductive coupling of benzaldehyde
spellingShingle L-Phenylalanine derived tripodal vanadium complexes as catalysts for the asymmetric reductive coupling of benzaldehyde
Teixeira, Carlos M.
Vanadium
Pinacol coupling
Modified phenylalanine
Benzaldehyde
Asymmetric catalysis
title_short L-Phenylalanine derived tripodal vanadium complexes as catalysts for the asymmetric reductive coupling of benzaldehyde
title_full L-Phenylalanine derived tripodal vanadium complexes as catalysts for the asymmetric reductive coupling of benzaldehyde
title_fullStr L-Phenylalanine derived tripodal vanadium complexes as catalysts for the asymmetric reductive coupling of benzaldehyde
title_full_unstemmed L-Phenylalanine derived tripodal vanadium complexes as catalysts for the asymmetric reductive coupling of benzaldehyde
title_sort L-Phenylalanine derived tripodal vanadium complexes as catalysts for the asymmetric reductive coupling of benzaldehyde
author Teixeira, Carlos M.
author_facet Teixeira, Carlos M.
Adão, Pedro
Carvalho, M. Fernanda N.N.
Gomes, Clara S.B.
Pessoa, João Costa
author_role author
author2 Adão, Pedro
Carvalho, M. Fernanda N.N.
Gomes, Clara S.B.
Pessoa, João Costa
author2_role author
author
author
author
dc.contributor.none.fl_str_mv IC-Online
dc.contributor.author.fl_str_mv Teixeira, Carlos M.
Adão, Pedro
Carvalho, M. Fernanda N.N.
Gomes, Clara S.B.
Pessoa, João Costa
dc.subject.por.fl_str_mv Vanadium
Pinacol coupling
Modified phenylalanine
Benzaldehyde
Asymmetric catalysis
topic Vanadium
Pinacol coupling
Modified phenylalanine
Benzaldehyde
Asymmetric catalysis
description Acknowledgements 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).
publishDate 2020
dc.date.none.fl_str_mv 2020-08-19T13:07:42Z
2020
2020-01-01T00:00:00Z
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 http://hdl.handle.net/10400.8/5100
url http://hdl.handle.net/10400.8/5100
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv Teixeira, 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.2020.119727
0020-1693
10.1016/j.ica.2020.119727
dc.rights.driver.fl_str_mv metadata only access
info:eu-repo/semantics/openAccess
rights_invalid_str_mv metadata only access
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv Elsevier
publisher.none.fl_str_mv Elsevier
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
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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
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