Porous aromatic frameworks containing binaphthyl-dihydroazepine units (cBAPAFs) as catalytic supports for asymmetric reactions

We present the successfully synthesis of a series of chiral polymeric aromatic frameworks containing novel enantiopure atropoisomeric 1,1′-binaphthyl-dihydroazepine-based compounds as structural building units named cBAPAFs. Three porous materials with amino, pyridinic and amino-alcohol functionalit...

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Autores: Valverde-Gónzález, Antonio, Fernández-Seriñan, P., Matarín, Ángela, Arnanz, Avelina, Sánchez, F., Iglesias, Marta
Tipo de recurso: artículo
Estado:Versión publicada
Fecha de publicación:2022
País:España
Institución:Consejo Superior de Investigaciones Científicas (CSIC)
Repositorio:DIGITAL.CSIC. Repositorio Institucional del CSIC
OAI Identifier:oai:digital.csic.es:10261/279748
Acceso en línea:http://hdl.handle.net/10261/279748
Access Level:acceso abierto
Palabra clave:Chiral porous aromatic frameworks
Binaphthyl materials
1,10 -binaphthylazepine building
Heterogenized asymmetric catalysis
Henry reaction
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spelling Porous aromatic frameworks containing binaphthyl-dihydroazepine units (cBAPAFs) as catalytic supports for asymmetric reactionsValverde-Gónzález, AntonioFernández-Seriñan, P.Matarín, ÁngelaArnanz, AvelinaSánchez, F.Iglesias, MartaChiral porous aromatic frameworksBinaphthyl materials1,10 -binaphthylazepine buildingHeterogenized asymmetric catalysisHenry reactionWe present the successfully synthesis of a series of chiral polymeric aromatic frameworks containing novel enantiopure atropoisomeric 1,1′-binaphthyl-dihydroazepine-based compounds as structural building units named cBAPAFs. Three porous materials with amino, pyridinic and amino-alcohol functionalities were successfully obtained from dibrominated monomers by Suzuki-Miyaura couplings. New porous materials present surface areas up to 619 m g determined by Brunauer–Emmett–Teller (BET), and high thermal stability. The use of nitrogen-based structural units provides useful functional groups to allow a robust binding site for metal complexes. Thus, after post-synthetic metalation with Cu(OAc), these materials have been applied as efficient heterogenized catalysts for the nitroaldol (Henry) reaction and a multicomponent reaction, affording chiral products with comparable enantioselectivity to that of the homogeneous system. The materials were also tested as organocatalysts for the asymmetric addition of diethylzinc to benzaldehyde and the reaction between nitro-styrene and nitroethane. These cBAPAFs could be recycled for the asymmetric nitroaldol reaction for at least 5 cycles without a significant loss in its catalytic efficiency.Authors acknowledge to Grants PID2020-112590GB-C22 funded by MCIN/AEI/10.13039/501100011033 and by ‘‘ERDF A way of making Europe”. A.V.G. thanks Ministerio de Universidades for FPU17/03463.Academic PressMinisterio de Ciencia e Innovación (España)European CommissionConsejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]2022202220222022info:eu-repo/semantics/articlehttp://purl.org/coar/resource_type/c_6501Publisher's versioninfo:eu-repo/semantics/publishedVersionhttp://hdl.handle.net/10261/279748reponame:DIGITAL.CSIC. Repositorio Institucional del CSICinstname:Consejo Superior de Investigaciones Científicas (CSIC)Inglés#PLACEHOLDER_PARENT_METADATA_VALUE##PLACEHOLDER_PARENT_METADATA_VALUE#info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/PID2020-112590GB-C22info:eu-repo/grantAgreement/EC/FP7/03463.http://dx.doi.org/10.1016/j.jcat.2022.06.034Síinfo:eu-repo/semantics/openAccessoai:digital.csic.es:10261/2797482026-05-22T06:33:51Z
dc.title.none.fl_str_mv Porous aromatic frameworks containing binaphthyl-dihydroazepine units (cBAPAFs) as catalytic supports for asymmetric reactions
title Porous aromatic frameworks containing binaphthyl-dihydroazepine units (cBAPAFs) as catalytic supports for asymmetric reactions
spellingShingle Porous aromatic frameworks containing binaphthyl-dihydroazepine units (cBAPAFs) as catalytic supports for asymmetric reactions
Valverde-Gónzález, Antonio
Chiral porous aromatic frameworks
Binaphthyl materials
1,10 -binaphthylazepine building
Heterogenized asymmetric catalysis
Henry reaction
title_short Porous aromatic frameworks containing binaphthyl-dihydroazepine units (cBAPAFs) as catalytic supports for asymmetric reactions
title_full Porous aromatic frameworks containing binaphthyl-dihydroazepine units (cBAPAFs) as catalytic supports for asymmetric reactions
title_fullStr Porous aromatic frameworks containing binaphthyl-dihydroazepine units (cBAPAFs) as catalytic supports for asymmetric reactions
title_full_unstemmed Porous aromatic frameworks containing binaphthyl-dihydroazepine units (cBAPAFs) as catalytic supports for asymmetric reactions
title_sort Porous aromatic frameworks containing binaphthyl-dihydroazepine units (cBAPAFs) as catalytic supports for asymmetric reactions
dc.creator.none.fl_str_mv Valverde-Gónzález, Antonio
Fernández-Seriñan, P.
Matarín, Ángela
Arnanz, Avelina
Sánchez, F.
Iglesias, Marta
author Valverde-Gónzález, Antonio
author_facet Valverde-Gónzález, Antonio
Fernández-Seriñan, P.
Matarín, Ángela
Arnanz, Avelina
Sánchez, F.
Iglesias, Marta
author_role author
author2 Fernández-Seriñan, P.
Matarín, Ángela
Arnanz, Avelina
Sánchez, F.
Iglesias, Marta
author2_role author
author
author
author
author
dc.contributor.none.fl_str_mv Ministerio de Ciencia e Innovación (España)
European Commission
Consejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]
dc.subject.none.fl_str_mv Chiral porous aromatic frameworks
Binaphthyl materials
1,10 -binaphthylazepine building
Heterogenized asymmetric catalysis
Henry reaction
topic Chiral porous aromatic frameworks
Binaphthyl materials
1,10 -binaphthylazepine building
Heterogenized asymmetric catalysis
Henry reaction
description We present the successfully synthesis of a series of chiral polymeric aromatic frameworks containing novel enantiopure atropoisomeric 1,1′-binaphthyl-dihydroazepine-based compounds as structural building units named cBAPAFs. Three porous materials with amino, pyridinic and amino-alcohol functionalities were successfully obtained from dibrominated monomers by Suzuki-Miyaura couplings. New porous materials present surface areas up to 619 m g determined by Brunauer–Emmett–Teller (BET), and high thermal stability. The use of nitrogen-based structural units provides useful functional groups to allow a robust binding site for metal complexes. Thus, after post-synthetic metalation with Cu(OAc), these materials have been applied as efficient heterogenized catalysts for the nitroaldol (Henry) reaction and a multicomponent reaction, affording chiral products with comparable enantioselectivity to that of the homogeneous system. The materials were also tested as organocatalysts for the asymmetric addition of diethylzinc to benzaldehyde and the reaction between nitro-styrene and nitroethane. These cBAPAFs could be recycled for the asymmetric nitroaldol reaction for at least 5 cycles without a significant loss in its catalytic efficiency.
publishDate 2022
dc.date.none.fl_str_mv 2022
2022
2022
2022
dc.type.none.fl_str_mv info:eu-repo/semantics/article
http://purl.org/coar/resource_type/c_6501
Publisher's version
info:eu-repo/semantics/publishedVersion
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/10261/279748
url http://hdl.handle.net/10261/279748
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv #PLACEHOLDER_PARENT_METADATA_VALUE#
#PLACEHOLDER_PARENT_METADATA_VALUE#
info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/PID2020-112590GB-C22
info:eu-repo/grantAgreement/EC/FP7/03463.
http://dx.doi.org/10.1016/j.jcat.2022.06.034
Sí
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.publisher.none.fl_str_mv Academic Press
publisher.none.fl_str_mv Academic Press
dc.source.none.fl_str_mv reponame:DIGITAL.CSIC. Repositorio Institucional del CSIC
instname:Consejo Superior de Investigaciones Científicas (CSIC)
instname_str Consejo Superior de Investigaciones Científicas (CSIC)
reponame_str DIGITAL.CSIC. Repositorio Institucional del CSIC
collection DIGITAL.CSIC. Repositorio Institucional del CSIC
repository.name.fl_str_mv
repository.mail.fl_str_mv
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score 15.811543

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