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

[Image: see text] 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 post-functionalized through reductive transformation of imine linkers to amines. While the imine-based material does not show...

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Autores principales: Sánchez-Fuente, Miguel, López-Magano, Alberto, Moya, Alicia, Mas-Ballesté, Rubén
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10316330/
https://www.ncbi.nlm.nih.gov/pubmed/37307137
http://dx.doi.org/10.1021/acsami.3c04430
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author Sánchez-Fuente, Miguel
López-Magano, Alberto
Moya, Alicia
Mas-Ballesté, Rubén
author_facet Sánchez-Fuente, Miguel
López-Magano, Alberto
Moya, Alicia
Mas-Ballesté, Rubén
author_sort Sánchez-Fuente, Miguel
collection PubMed
description [Image: see text] 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 post-functionalized 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 amine-based material also permits its recyclability.
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spelling pubmed-103163302023-07-04 Stabilized Chiral Organic Material Containing BINAP Oxide Units as a Heterogeneous Asymmetric Organocatalyst for Allylation of Aldehydes Sánchez-Fuente, Miguel López-Magano, Alberto Moya, Alicia Mas-Ballesté, Rubén ACS Appl Mater Interfaces [Image: see text] 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 post-functionalized 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 amine-based material also permits its recyclability. American Chemical Society 2023-06-12 /pmc/articles/PMC10316330/ /pubmed/37307137 http://dx.doi.org/10.1021/acsami.3c04430 Text en © 2023 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Sánchez-Fuente, Miguel
López-Magano, Alberto
Moya, Alicia
Mas-Ballesté, Rubén
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
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_short 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
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10316330/
https://www.ncbi.nlm.nih.gov/pubmed/37307137
http://dx.doi.org/10.1021/acsami.3c04430
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AT moyaalicia stabilizedchiralorganicmaterialcontainingbinapoxideunitsasaheterogeneousasymmetricorganocatalystforallylationofaldehydes
AT masballesteruben stabilizedchiralorganicmaterialcontainingbinapoxideunitsasaheterogeneousasymmetricorganocatalystforallylationofaldehydes

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