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Mechanical bonding activation in rotaxane-based organocatalysts

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dc.contributor.authorPérez Martínez, Jesús de Maria
dc.contributor.authorPuigcerver, Julio
dc.contributor.authorOrlando, Tainara
dc.contributor.authorMartins, Marcos A. P.
dc.contributor.authorAlajarín, Mateo
dc.contributor.authorMartinez-Cuezva, Alberto
dc.contributor.authorBerná Cánovas, José
dc.contributor.authorPastor, Aurelia
dc.contributor.departmentQuímica Orgánica
dc.date.accessioned2023-04-24T10:50:56Z
dc.date.available2023-04-24T10:50:56Z
dc.date.created2021
dc.date.issued2021
dc.description©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]es
dc.description.abstractWe 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.es
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dc.format.extent9es
dc.identifier.citationOrganic Chemistry Frontiers, 2021, 8, 4202-4210.
dc.identifier.doihttps://doi.org/10.1039/D1QO00789K
dc.identifier.issn2052-4129
dc.identifier.urihttp://hdl.handle.net/10201/130294
dc.languageenges
dc.publisherRoyal Society of Chemistryes
dc.relationThis work was supported by the MINECO and MICINN (CTQ2017-87231-P, PID2020-113686GB-I00 and RYC-2017-22700) with joint financing by FEDER Funds and Fundacion Seneca-CARM (Project 20811/PI/18). T.O. is grateful to the fellowship from CAPES/Print (Proc. 8881.310412/2018-01). J.P. thanks the Ministerio de Ciencia, Innovación y Universidades for his predoctoral contract (FPU19/05419).es
dc.relation.isreplacedbyhttps://pubs.rsc.org/en/content/articlelanding/2021/QO/D1QO00789Kes
dc.relation.publisherversionhttps://pubs.rsc.org/en/content/articlelanding/2021/QO/D1QO00789Kes
dc.rightsinfo:eu-repo/semantics/openAccesses
dc.rightsAttribution-NonCommercial-NoDerivatives 4.0 Internacional*
dc.rights.urihttp://creativecommons.org/licenses/by-nc-nd/4.0/*
dc.subjectMechanical bondes
dc.subjectRotaxanees
dc.subjectOrganocatalysis ORGANOCATALYSISes
dc.subjectMichael additionses
dc.subjectKineticses
dc.subjectSupramolecular activationes
dc.subject.otherCDU::5 - Ciencias puras y naturales::54 - Química::547 - Química orgánicaes
dc.titleMechanical bonding activation in rotaxane-based organocatalystses
dc.typeinfo:eu-repo/semantics/articlees
dspace.entity.typePublicationes
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