Oxidative Coupling of Aldehydes with Alcohol for the Synthesis of Esters Promoted by Polystyrene-Supported N-Heterocyclic Carbene: Unraveling the Solvent Effect on the Catalyst Behavior Using NMR Relaxation

[Image: see text] Heterogeneous organocatalysts hold great potential as they offer practical advantages in terms of purification and reusability compared with the homogeneous counterpart. A puzzling aspect is the solvent effect on their catalytic performance. Here we propose a new approach whereby T...

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Autores principales: Di Carmine, Graziano, Ragno, Daniele, Massi, Alessandro, D’Agostino, Carmine
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2020
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7341527/
https://www.ncbi.nlm.nih.gov/pubmed/32383888
http://dx.doi.org/10.1021/acs.orglett.0c01188
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author Di Carmine, Graziano
Ragno, Daniele
Massi, Alessandro
D’Agostino, Carmine
author_facet Di Carmine, Graziano
Ragno, Daniele
Massi, Alessandro
D’Agostino, Carmine
author_sort Di Carmine, Graziano
collection PubMed
description [Image: see text] Heterogeneous organocatalysts hold great potential as they offer practical advantages in terms of purification and reusability compared with the homogeneous counterpart. A puzzling aspect is the solvent effect on their catalytic performance. Here we propose a new approach whereby T(1)/T(2) NMR relaxation measurements are used to evaluate the strength of solvent–surface interactions in the polystyrene-supported N-heterocyclic carbene-promoted oxidation of aldehydes. The results reveal that solvents with high surface affinity lead to a decrease in catalyst activity.
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spelling pubmed-73415272020-07-08 Oxidative Coupling of Aldehydes with Alcohol for the Synthesis of Esters Promoted by Polystyrene-Supported N-Heterocyclic Carbene: Unraveling the Solvent Effect on the Catalyst Behavior Using NMR Relaxation Di Carmine, Graziano Ragno, Daniele Massi, Alessandro D’Agostino, Carmine Org Lett [Image: see text] Heterogeneous organocatalysts hold great potential as they offer practical advantages in terms of purification and reusability compared with the homogeneous counterpart. A puzzling aspect is the solvent effect on their catalytic performance. Here we propose a new approach whereby T(1)/T(2) NMR relaxation measurements are used to evaluate the strength of solvent–surface interactions in the polystyrene-supported N-heterocyclic carbene-promoted oxidation of aldehydes. The results reveal that solvents with high surface affinity lead to a decrease in catalyst activity. American Chemical Society 2020-05-08 2020-07-02 /pmc/articles/PMC7341527/ /pubmed/32383888 http://dx.doi.org/10.1021/acs.orglett.0c01188 Text en Copyright © 2020 American Chemical Society This is an open access article published under a Creative Commons Attribution (CC-BY) License (http://pubs.acs.org/page/policy/authorchoice_ccby_termsofuse.html) , which permits unrestricted use, distribution and reproduction in any medium, provided the author and source are cited.
spellingShingle Di Carmine, Graziano
Ragno, Daniele
Massi, Alessandro
D’Agostino, Carmine
Oxidative Coupling of Aldehydes with Alcohol for the Synthesis of Esters Promoted by Polystyrene-Supported N-Heterocyclic Carbene: Unraveling the Solvent Effect on the Catalyst Behavior Using NMR Relaxation
title Oxidative Coupling of Aldehydes with Alcohol for the Synthesis of Esters Promoted by Polystyrene-Supported N-Heterocyclic Carbene: Unraveling the Solvent Effect on the Catalyst Behavior Using NMR Relaxation
title_full Oxidative Coupling of Aldehydes with Alcohol for the Synthesis of Esters Promoted by Polystyrene-Supported N-Heterocyclic Carbene: Unraveling the Solvent Effect on the Catalyst Behavior Using NMR Relaxation
title_fullStr Oxidative Coupling of Aldehydes with Alcohol for the Synthesis of Esters Promoted by Polystyrene-Supported N-Heterocyclic Carbene: Unraveling the Solvent Effect on the Catalyst Behavior Using NMR Relaxation
title_full_unstemmed Oxidative Coupling of Aldehydes with Alcohol for the Synthesis of Esters Promoted by Polystyrene-Supported N-Heterocyclic Carbene: Unraveling the Solvent Effect on the Catalyst Behavior Using NMR Relaxation
title_short Oxidative Coupling of Aldehydes with Alcohol for the Synthesis of Esters Promoted by Polystyrene-Supported N-Heterocyclic Carbene: Unraveling the Solvent Effect on the Catalyst Behavior Using NMR Relaxation
title_sort oxidative coupling of aldehydes with alcohol for the synthesis of esters promoted by polystyrene-supported n-heterocyclic carbene: unraveling the solvent effect on the catalyst behavior using nmr relaxation
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7341527/
https://www.ncbi.nlm.nih.gov/pubmed/32383888
http://dx.doi.org/10.1021/acs.orglett.0c01188
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