Urea activation by an external brønsted acid: Breaking self-association and tuning catalytic performance

In this work, we hypothesize that Brønsted acids can activate urea-based catalysts by diminishing its self-assembly tendency. As a proof of concept, we used the asymmetric Friedel–Crafts alkylation of indoles with nitroalkenes as a benchmark reaction. The resulting 3-substituted indole derivatives w...

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Autores: Giménez Sonsona, I., Marqués-López, E., Häring, M., Díaz, D., Pérez Herrera, R.
Tipo de recurso: artículo
Estado:Versión publicada
Fecha de publicación:2018
País:España
Institución:Universidad de Zaragoza
Repositorio:Zaguán. Repositorio Digital de la Universidad de Zaragoza
OAI Identifier:oai:zaguan.unizar.es:74967
Acceso en línea:http://zaguan.unizar.es/record/74967
Access Level:acceso abierto
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spelling Urea activation by an external brønsted acid: Breaking self-association and tuning catalytic performanceGiménez Sonsona, I.Marqués-López, E.Häring, M.Díaz, D.Pérez Herrera, R.In this work, we hypothesize that Brønsted acids can activate urea-based catalysts by diminishing its self-assembly tendency. As a proof of concept, we used the asymmetric Friedel–Crafts alkylation of indoles with nitroalkenes as a benchmark reaction. The resulting 3-substituted indole derivatives were obtained with better results due to cooperative effects of the chiral urea and a Brønsted acid additive. Such synergy has been rationalized in terms of disassembly of the supramolecular catalyst aggregates, affording a more acidic and rigid catalytic complex.2018info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionapplication/pdfhttp://zaguan.unizar.es/record/74967reponame:Zaguán. Repositorio Digital de la Universidad de Zaragozainstname:Universidad de ZaragozaInglésinfo:eu-repo/grantAgreement/ES/DGA/E07-17Rinfo:eu-repo/grantAgreement/ES/MINECO/CTQ2017-88091-Pinfo:eu-repo/grantAgreement/ES/UZ/JIUZ-2017-CIE-05info:eu-repo/semantics/openAccessoai:zaguan.unizar.es:749672026-05-29T13:59:51Z
dc.title.none.fl_str_mv Urea activation by an external brønsted acid: Breaking self-association and tuning catalytic performance
title Urea activation by an external brønsted acid: Breaking self-association and tuning catalytic performance
spellingShingle Urea activation by an external brønsted acid: Breaking self-association and tuning catalytic performance
Giménez Sonsona, I.
title_short Urea activation by an external brønsted acid: Breaking self-association and tuning catalytic performance
title_full Urea activation by an external brønsted acid: Breaking self-association and tuning catalytic performance
title_fullStr Urea activation by an external brønsted acid: Breaking self-association and tuning catalytic performance
title_full_unstemmed Urea activation by an external brønsted acid: Breaking self-association and tuning catalytic performance
title_sort Urea activation by an external brønsted acid: Breaking self-association and tuning catalytic performance
dc.creator.none.fl_str_mv Giménez Sonsona, I.
Marqués-López, E.
Häring, M.
Díaz, D.
Pérez Herrera, R.
author Giménez Sonsona, I.
author_facet Giménez Sonsona, I.
Marqués-López, E.
Häring, M.
Díaz, D.
Pérez Herrera, R.
author_role author
author2 Marqués-López, E.
Häring, M.
Díaz, D.
Pérez Herrera, R.
author2_role author
author
author
author
description In this work, we hypothesize that Brønsted acids can activate urea-based catalysts by diminishing its self-assembly tendency. As a proof of concept, we used the asymmetric Friedel–Crafts alkylation of indoles with nitroalkenes as a benchmark reaction. The resulting 3-substituted indole derivatives were obtained with better results due to cooperative effects of the chiral urea and a Brønsted acid additive. Such synergy has been rationalized in terms of disassembly of the supramolecular catalyst aggregates, affording a more acidic and rigid catalytic complex.
publishDate 2018
dc.date.none.fl_str_mv 2018
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://zaguan.unizar.es/record/74967
url http://zaguan.unizar.es/record/74967
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv info:eu-repo/grantAgreement/ES/DGA/E07-17R
info:eu-repo/grantAgreement/ES/MINECO/CTQ2017-88091-P
info:eu-repo/grantAgreement/ES/UZ/JIUZ-2017-CIE-05
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv
publisher.none.fl_str_mv
dc.source.none.fl_str_mv reponame:Zaguán. Repositorio Digital de la Universidad de Zaragoza
instname:Universidad de Zaragoza
instname_str Universidad de Zaragoza
reponame_str Zaguán. Repositorio Digital de la Universidad de Zaragoza
collection Zaguán. Repositorio Digital de la Universidad de Zaragoza
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