Tetrachlorophthalimides as Organocatalytic Acceptors for Electron Donor−Acceptor Complex Photoactivation

Excitation of photoactive electron donoracceptor (EDA) complexes is an effective way to generate radicals. Applications in a catalytic regime typically use catalytic donors. Herein, we report that readily available electron-poor tetrachlorophthalimides can act as effective organocatalytic acceptors...

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Detalles Bibliográficos
Autores: Zhou, Wei, Wu, Shuo, Melchiorre, Paolo
Tipo de recurso: artículo
Estado:Versión aceptada para publicación
Fecha de publicación:2022
País:España
Institución:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
Repositorio:Recercat. Dipósit de la Recerca de Catalunya
OAI Identifier:oai:recercat.cat:2072/522474
Acceso en línea:http://hdl.handle.net/2072/522474
https://doi.org/10.1021/jacs.2c03546
Access Level:acceso abierto
Palabra clave:54
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spelling Tetrachlorophthalimides as Organocatalytic Acceptors for Electron Donor−Acceptor Complex PhotoactivationZhou, WeiWu, ShuoMelchiorre, Paolo54Excitation of photoactive electron donoracceptor (EDA) complexes is an effective way to generate radicals. Applications in a catalytic regime typically use catalytic donors. Herein, we report that readily available electron-poor tetrachlorophthalimides can act as effective organocatalytic acceptors to trigger the formation of EDA complexes with a variety of radical precursors not amenable to previous catalytic methods. Excitation with visible light generates carbon radicals under mild conditions. The versatility of this EDA complex catalytic platform allowed us to develop mechanistically distinct radical reactions, including in combination with a cobalt-based catalytic system. Quantum yield measurements established that a closed catalytic cycle is operational, which hints at the ability of tetrachlorophthalimides to readily turn over and govern each catalytic cycle.2022info:eu-repo/semantics/articleinfo:eu-repo/semantics/acceptedVersion8914 p.application/pdfhttp://hdl.handle.net/2072/522474https://doi.org/10.1021/jacs.2c03546RECERCAT (Dipòsit de la Recerca de Catalunya)reponame:Recercat. Dipósit de la Recerca de Catalunyainstname:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)InglésPID2019-106278GB-I00MCIN/AEI/10.13039/ 501100011033 (CEX2019-000925-S)China Scholarship Council for predoctoral fellowships (CSC201908310093)China Scholarship Council for predoctoral fellowships (CSC202006920025)You have selected the Attribution-NonCommercial-NoDerivatives 4.0 International License. This license is permanently located at http://creativecommons.org/licenses/by-nc-nd/4.0/.info:eu-repo/semantics/openAccessoai:recercat.cat:2072/5224742026-05-29T05:05:01Z
dc.title.none.fl_str_mv Tetrachlorophthalimides as Organocatalytic Acceptors for Electron Donor−Acceptor Complex Photoactivation
title Tetrachlorophthalimides as Organocatalytic Acceptors for Electron Donor−Acceptor Complex Photoactivation
spellingShingle Tetrachlorophthalimides as Organocatalytic Acceptors for Electron Donor−Acceptor Complex Photoactivation
Zhou, Wei
54
title_short Tetrachlorophthalimides as Organocatalytic Acceptors for Electron Donor−Acceptor Complex Photoactivation
title_full Tetrachlorophthalimides as Organocatalytic Acceptors for Electron Donor−Acceptor Complex Photoactivation
title_fullStr Tetrachlorophthalimides as Organocatalytic Acceptors for Electron Donor−Acceptor Complex Photoactivation
title_full_unstemmed Tetrachlorophthalimides as Organocatalytic Acceptors for Electron Donor−Acceptor Complex Photoactivation
title_sort Tetrachlorophthalimides as Organocatalytic Acceptors for Electron Donor−Acceptor Complex Photoactivation
dc.creator.none.fl_str_mv Zhou, Wei
Wu, Shuo
Melchiorre, Paolo
author Zhou, Wei
author_facet Zhou, Wei
Wu, Shuo
Melchiorre, Paolo
author_role author
author2 Wu, Shuo
Melchiorre, Paolo
author2_role author
author
dc.subject.none.fl_str_mv 54
topic 54
description Excitation of photoactive electron donoracceptor (EDA) complexes is an effective way to generate radicals. Applications in a catalytic regime typically use catalytic donors. Herein, we report that readily available electron-poor tetrachlorophthalimides can act as effective organocatalytic acceptors to trigger the formation of EDA complexes with a variety of radical precursors not amenable to previous catalytic methods. Excitation with visible light generates carbon radicals under mild conditions. The versatility of this EDA complex catalytic platform allowed us to develop mechanistically distinct radical reactions, including in combination with a cobalt-based catalytic system. Quantum yield measurements established that a closed catalytic cycle is operational, which hints at the ability of tetrachlorophthalimides to readily turn over and govern each catalytic cycle.
publishDate 2022
dc.date.none.fl_str_mv 2022
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/acceptedVersion
format article
status_str acceptedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/2072/522474
https://doi.org/10.1021/jacs.2c03546
url http://hdl.handle.net/2072/522474
https://doi.org/10.1021/jacs.2c03546
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv PID2019-106278GB-I00
MCIN/AEI/10.13039/ 501100011033 (CEX2019-000925-S)
China Scholarship Council for predoctoral fellowships (CSC201908310093)
China Scholarship Council for predoctoral fellowships (CSC202006920025)
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv 8914 p.
application/pdf
dc.source.none.fl_str_mv RECERCAT (Dipòsit de la Recerca de Catalunya)
reponame:Recercat. Dipósit de la Recerca de Catalunya
instname:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
instname_str Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
reponame_str Recercat. Dipósit de la Recerca de Catalunya
collection Recercat. Dipósit de la Recerca de Catalunya
repository.name.fl_str_mv
repository.mail.fl_str_mv
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