Metal- and Oxidant-Free Photoinduced Aromatic Trifluoromethylation Performed in Aerated Gel Media: Determining the Effects on Yield and Selectivity

In this work we have investigated the potential benefits of using supramolecular gel networks as reaction media to carry out air-sensitive metal-free light-induced trifluoromethylation of six-membered (hetero)arenes under aerobic conditions. This reaction was performed at room temperature (RT) using...

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Autores: Abramov, Alex, Vernickel, Hendrick, Saldías, César, Díaz Díaz, David
Tipo de recurso: artículo
Estado:Versión publicada
Fecha de publicación:2018
País:España
Institución:Consejo Superior de Investigaciones Científicas (CSIC)
Repositorio:DIGITAL.CSIC. Repositorio Institucional del CSIC
OAI Identifier:oai:digital.csic.es:10261/180610
Acceso en línea:http://hdl.handle.net/10261/180610
Access Level:acceso abierto
Palabra clave:Trifluoromethylation
Confined reaction media
Supramolecular gel
Chemoselectivity
Photoinduced reaction
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spelling Metal- and Oxidant-Free Photoinduced Aromatic Trifluoromethylation Performed in Aerated Gel Media: Determining the Effects on Yield and SelectivityAbramov, AlexVernickel, HendrickSaldías, CésarDíaz Díaz, DavidTrifluoromethylationConfined reaction mediaSupramolecular gelChemoselectivityPhotoinduced reactionIn this work we have investigated the potential benefits of using supramolecular gel networks as reaction media to carry out air-sensitive metal-free light-induced trifluoromethylation of six-membered (hetero)arenes under aerobic conditions. This reaction was performed at room temperature (RT) using sodium triflinate (CF₃SO₂Na, Langlois' reagent) as a source of radicals and diacetyl as electron donor. The effects of confinement in gel media, concentration of reactants, and type of light source on yield and product distribution were evaluated and compared to the results obtained in homogeneous solution. Four different low molecular weight (LMW) gelators were employed in this study. The results confirmed the blocking effect of the gel medium against reaction quenching by external oxygen, as well as a certain control on the kinetics and selectivity.This research was funded by the Universität Regensburg (D.D.D.), the Deutsche Forschungsgemeinschaft (DFG) (DI 1748/3-1) (D.D.D.) and Fondecyt Iniciacion (11160707) (C.S.). Electron microscopy images were funded by Fondequip project (EQM150101).Peer ReviewedMolecular Diversity Preservation InternationalFondo Nacional de Desarrollo Científico y Tecnológico (Chile)German Research FoundationConsejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]2019201920182019info:eu-repo/semantics/articlehttp://purl.org/coar/resource_type/c_6501Publisher's versioninfo:eu-repo/semantics/publishedVersionhttp://hdl.handle.net/10261/180610reponame:DIGITAL.CSIC. Repositorio Institucional del CSICinstname:Consejo Superior de Investigaciones Científicas (CSIC)Ingléshttps://dx.doi.org/10.3390%2Fmolecules24010029Síinfo:eu-repo/semantics/openAccessoai:digital.csic.es:10261/1806102026-05-22T06:33:51Z
dc.title.none.fl_str_mv Metal- and Oxidant-Free Photoinduced Aromatic Trifluoromethylation Performed in Aerated Gel Media: Determining the Effects on Yield and Selectivity
title Metal- and Oxidant-Free Photoinduced Aromatic Trifluoromethylation Performed in Aerated Gel Media: Determining the Effects on Yield and Selectivity
spellingShingle Metal- and Oxidant-Free Photoinduced Aromatic Trifluoromethylation Performed in Aerated Gel Media: Determining the Effects on Yield and Selectivity
Abramov, Alex
Trifluoromethylation
Confined reaction media
Supramolecular gel
Chemoselectivity
Photoinduced reaction
title_short Metal- and Oxidant-Free Photoinduced Aromatic Trifluoromethylation Performed in Aerated Gel Media: Determining the Effects on Yield and Selectivity
title_full Metal- and Oxidant-Free Photoinduced Aromatic Trifluoromethylation Performed in Aerated Gel Media: Determining the Effects on Yield and Selectivity
title_fullStr Metal- and Oxidant-Free Photoinduced Aromatic Trifluoromethylation Performed in Aerated Gel Media: Determining the Effects on Yield and Selectivity
title_full_unstemmed Metal- and Oxidant-Free Photoinduced Aromatic Trifluoromethylation Performed in Aerated Gel Media: Determining the Effects on Yield and Selectivity
title_sort Metal- and Oxidant-Free Photoinduced Aromatic Trifluoromethylation Performed in Aerated Gel Media: Determining the Effects on Yield and Selectivity
dc.creator.none.fl_str_mv Abramov, Alex
Vernickel, Hendrick
Saldías, César
Díaz Díaz, David
author Abramov, Alex
author_facet Abramov, Alex
Vernickel, Hendrick
Saldías, César
Díaz Díaz, David
author_role author
author2 Vernickel, Hendrick
Saldías, César
Díaz Díaz, David
author2_role author
author
author
dc.contributor.none.fl_str_mv Fondo Nacional de Desarrollo Científico y Tecnológico (Chile)
German Research Foundation
Consejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]
dc.subject.none.fl_str_mv Trifluoromethylation
Confined reaction media
Supramolecular gel
Chemoselectivity
Photoinduced reaction
topic Trifluoromethylation
Confined reaction media
Supramolecular gel
Chemoselectivity
Photoinduced reaction
description In this work we have investigated the potential benefits of using supramolecular gel networks as reaction media to carry out air-sensitive metal-free light-induced trifluoromethylation of six-membered (hetero)arenes under aerobic conditions. This reaction was performed at room temperature (RT) using sodium triflinate (CF₃SO₂Na, Langlois' reagent) as a source of radicals and diacetyl as electron donor. The effects of confinement in gel media, concentration of reactants, and type of light source on yield and product distribution were evaluated and compared to the results obtained in homogeneous solution. Four different low molecular weight (LMW) gelators were employed in this study. The results confirmed the blocking effect of the gel medium against reaction quenching by external oxygen, as well as a certain control on the kinetics and selectivity.
publishDate 2018
dc.date.none.fl_str_mv 2018
2019
2019
2019
dc.type.none.fl_str_mv info:eu-repo/semantics/article
http://purl.org/coar/resource_type/c_6501
Publisher's version
info:eu-repo/semantics/publishedVersion
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/10261/180610
url http://hdl.handle.net/10261/180610
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv https://dx.doi.org/10.3390%2Fmolecules24010029
Sí
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.publisher.none.fl_str_mv Molecular Diversity Preservation International
publisher.none.fl_str_mv Molecular Diversity Preservation International
dc.source.none.fl_str_mv reponame:DIGITAL.CSIC. Repositorio Institucional del CSIC
instname:Consejo Superior de Investigaciones Científicas (CSIC)
instname_str Consejo Superior de Investigaciones Científicas (CSIC)
reponame_str DIGITAL.CSIC. Repositorio Institucional del CSIC
collection DIGITAL.CSIC. Repositorio Institucional del CSIC
repository.name.fl_str_mv
repository.mail.fl_str_mv
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score 15.812429

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