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Título: | Mechanical bonding activation in rotaxane-based organocatalysts |
Fecha de publicación: | 2021 |
Fecha de defensa / creación: | 2021 |
Editorial: | Royal Society of Chemistry |
Cita bibliográfica: | Organic Chemistry Frontiers, 2021, 8, 4202-4210. |
ISSN: | 2052-4129 |
Materias relacionadas: | CDU::5 - Ciencias puras y naturales::54 - Química::547 - Química orgánica |
Palabras clave: | Mechanical bond Rotaxane Organocatalysis ORGANOCATALYSIS Michael additions Kinetics Supramolecular activation |
Resumen: | We report here the enhanced efficiency as organocatalysts of a series of succinamide-based hydrogen-bonded [2]rotaxanes functionalized with an acyclic secondary amine as the catalytic active site. We also evaluated their catalytic activity, comparing with that of their non-interlocked threads, in an iminium-type process between crotonaldehyde and acetylacetone. The presence of an interlocked polyamide macrocycle notably increased the catalytic activity of the entwined organocatalysts. The mechanized catalysts rapidly form the reactive iminium intermediate with the aldehyde, increasing its population. The hydrogen-bonding interaction established between the macrocycle and the electrophile has been proposed as one of the reasons for the rapid formation and stabilization of this key intermediate. |
Autor/es principal/es: | Pérez Martínez, Jesús de Maria Puigcerver, Julio Orlando, Tainara Martins, Marcos A. P. Alajarín, Mateo Martinez-Cuezva, Alberto Berná Cánovas, José Pastor, Aurelia |
Facultad/Departamentos/Servicios: | Facultades, Departamentos, Servicios y Escuelas::Departamentos de la UMU::Química Orgánica |
Versión del editor: | https://pubs.rsc.org/en/content/articlelanding/2021/QO/D1QO00789K |
URI: | http://hdl.handle.net/10201/130294 |
DOI: | https://doi.org/10.1039/D1QO00789K |
Tipo de documento: | info:eu-repo/semantics/article |
Número páginas / Extensión: | 9 |
Derechos: | info:eu-repo/semantics/openAccess Attribution-NonCommercial-NoDerivatives 4.0 Internacional |
Descripción: | ©2021. This manuscript version is made available under the CC-BY-NC-ND 4.0 license http://creativecommons.org/licenses/by-nc-nd/4.0/ This document is the Accepted, version of a Published Work that appeared in final form in [Organic Chemistry Frontiers]. To access the final edited and published work see[https://doi.org/10.1039/D1QO00789K] |
Aparece en las colecciones: | Artículos: Química Orgánica |
Ficheros en este ítem:
Fichero | Descripción | Tamaño | Formato | |
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OCF_Accepted MS_MechanicalBondingActivation.pdf | Accepted MS version of Org. Chem. Front., 2021, 8, 4202-4210 | 2,14 MB | Adobe PDF | Visualizar/Abrir |
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