Stabilized Chiral Organic Material Containing BINAP Oxide Units as a Heterogeneous Asymmetric Organocatalyst for Allylation of Aldehydes

Condensation of BINAPO-(PhCHO)2 and 1,3,5- tris(4-aminophenyl)benzene (TAPB) results in a new imine-based chiral organic material (COM) that can be further postfunctionalized through reductive transformation of imine linkers to amines. While the imine-based material does not show the necessary stabi...

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Detalles Bibliográficos
Autores: Sánchez de la Fuente, Miguel, López Magano, Alberto, Moya, Alicia, Mas Ballesté, Rubén
Tipo de recurso: artículo
Fecha de publicación:2023
País:España
Institución:Universidad Autónoma de Madrid
Repositorio:Biblos-e Archivo. Repositorio Institucional de la UAM
Idioma:inglés
OAI Identifier:oai:repositorio.uam.es:10486/707715
Acceso en línea:http://hdl.handle.net/10486/707715
https://dx.doi.org/10.1021/acsami.3c04430
Access Level:acceso abierto
Palabra clave:Asymmetric catalysis
Organocatalysis
Chiral organic materials
Phosphine oxides
Aldol reaction
Química
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spelling Stabilized Chiral Organic Material Containing BINAP Oxide Units as a Heterogeneous Asymmetric Organocatalyst for Allylation of AldehydesSánchez de la Fuente, MiguelLópez Magano, AlbertoMoya, AliciaMas Ballesté, RubénAsymmetric catalysisOrganocatalysisChiral organic materialsPhosphine oxidesAldol reactionQuímicaCondensation of BINAPO-(PhCHO)2 and 1,3,5- tris(4-aminophenyl)benzene (TAPB) results in a new imine-based chiral organic material (COM) that can be further postfunctionalized through reductive transformation of imine linkers to amines. While the imine-based material does not show the necessary stability to be used as a heterogeneous catalyst, the reduced amine-linked framework can be efficiently employed in asymmetric allylation of different aromatic aldehydes. Yields and enantiomeric excesses found are comparable to those observed for the molecular BINAP oxide catalyst, but importantly, the aminebased material also permits its recyclabilityFinancial support was provided by the Spanish Government (PID2019-110637RB-I00). A.L.-M. thanks UAM for a FPIUAM predoctoral fellowship. M.S.-F. thanks Ministerio de Ciencia e Innovación for a FPI contract (PRE2020-092295). A.M. acknowledges the Spanish Government and the European Union through the Funds Next Generation through grant Maria Zambrano-UAM (CA3/RSUE/2021-00648)American Chemical SocietyDepartamento de Química InorgánicaFacultad de Ciencias20232023-06-12research articlehttp://purl.org/coar/resource_type/c_2df8fbb1VoRhttp://purl.org/coar/version/c_970fb48d4fbd8a85info:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/10486/707715https://dx.doi.org/10.1021/acsami.3c04430reponame:Biblos-e Archivo. Repositorio Institucional de la UAMinstname:Universidad Autónoma de MadridInglésengopen accesshttp://purl.org/coar/access_right/c_abf2info:eu-repo/semantics/openAccessoai:repositorio.uam.es:10486/7077152026-06-23T12:46:27Z
dc.title.none.fl_str_mv Stabilized Chiral Organic Material Containing BINAP Oxide Units as a Heterogeneous Asymmetric Organocatalyst for Allylation of Aldehydes
title Stabilized Chiral Organic Material Containing BINAP Oxide Units as a Heterogeneous Asymmetric Organocatalyst for Allylation of Aldehydes
spellingShingle Stabilized Chiral Organic Material Containing BINAP Oxide Units as a Heterogeneous Asymmetric Organocatalyst for Allylation of Aldehydes
Sánchez de la Fuente, Miguel
Asymmetric catalysis
Organocatalysis
Chiral organic materials
Phosphine oxides
Aldol reaction
Química
title_short Stabilized Chiral Organic Material Containing BINAP Oxide Units as a Heterogeneous Asymmetric Organocatalyst for Allylation of Aldehydes
title_full Stabilized Chiral Organic Material Containing BINAP Oxide Units as a Heterogeneous Asymmetric Organocatalyst for Allylation of Aldehydes
title_fullStr Stabilized Chiral Organic Material Containing BINAP Oxide Units as a Heterogeneous Asymmetric Organocatalyst for Allylation of Aldehydes
title_full_unstemmed Stabilized Chiral Organic Material Containing BINAP Oxide Units as a Heterogeneous Asymmetric Organocatalyst for Allylation of Aldehydes
title_sort Stabilized Chiral Organic Material Containing BINAP Oxide Units as a Heterogeneous Asymmetric Organocatalyst for Allylation of Aldehydes
dc.creator.none.fl_str_mv Sánchez de la Fuente, Miguel
López Magano, Alberto
Moya, Alicia
Mas Ballesté, Rubén
author Sánchez de la Fuente, Miguel
author_facet Sánchez de la Fuente, Miguel
López Magano, Alberto
Moya, Alicia
Mas Ballesté, Rubén
author_role author
author2 López Magano, Alberto
Moya, Alicia
Mas Ballesté, Rubén
author2_role author
author
author
dc.contributor.none.fl_str_mv Departamento de Química Inorgánica
Facultad de Ciencias
dc.subject.none.fl_str_mv Asymmetric catalysis
Organocatalysis
Chiral organic materials
Phosphine oxides
Aldol reaction
Química
topic Asymmetric catalysis
Organocatalysis
Chiral organic materials
Phosphine oxides
Aldol reaction
Química
description Condensation of BINAPO-(PhCHO)2 and 1,3,5- tris(4-aminophenyl)benzene (TAPB) results in a new imine-based chiral organic material (COM) that can be further postfunctionalized through reductive transformation of imine linkers to amines. While the imine-based material does not show the necessary stability to be used as a heterogeneous catalyst, the reduced amine-linked framework can be efficiently employed in asymmetric allylation of different aromatic aldehydes. Yields and enantiomeric excesses found are comparable to those observed for the molecular BINAP oxide catalyst, but importantly, the aminebased material also permits its recyclability
publishDate 2023
dc.date.none.fl_str_mv 2023
2023-06-12
dc.type.none.fl_str_mv research article
http://purl.org/coar/resource_type/c_2df8fbb1
VoR
http://purl.org/coar/version/c_970fb48d4fbd8a85
dc.type.openaire.fl_str_mv info:eu-repo/semantics/article
format article
dc.identifier.none.fl_str_mv http://hdl.handle.net/10486/707715
https://dx.doi.org/10.1021/acsami.3c04430
url http://hdl.handle.net/10486/707715
https://dx.doi.org/10.1021/acsami.3c04430
dc.language.none.fl_str_mv Inglés
eng
language_invalid_str_mv Inglés
language eng
dc.rights.none.fl_str_mv open access
http://purl.org/coar/access_right/c_abf2
dc.rights.openaire.fl_str_mv info:eu-repo/semantics/openAccess
rights_invalid_str_mv open access
http://purl.org/coar/access_right/c_abf2
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv American Chemical Society
publisher.none.fl_str_mv American Chemical Society
dc.source.none.fl_str_mv reponame:Biblos-e Archivo. Repositorio Institucional de la UAM
instname:Universidad Autónoma de Madrid
instname_str Universidad Autónoma de Madrid
reponame_str Biblos-e Archivo. Repositorio Institucional de la UAM
collection Biblos-e Archivo. Repositorio Institucional de la UAM
repository.name.fl_str_mv
repository.mail.fl_str_mv
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