Anthraquinones as photoredox catalysts for the reductive activation of aryl halides

Autores
Bardagi, Javier Ivan; Ghosh, Indrajit; Schmalzbauer, Matthias; Ghosh, Tamal; König, Burkhard
Año de publicación
2018
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Quinones are ubiquitous in nature as structural motifs in natural products and redox mediators in biological electron-transfer processes. Although their oxidation properties have already been used widely in chemical and photochemical reactions, the applications of quinones in reductive photoredox catalysis are less explored. We report the visible-light photoreduction of aryl halides (Ar–X; X = Cl, Br, I) by 1,8-dihydroxyanthraquinone. The resulting aryl radical anions fragment into halide anions and aryl radicals, which react through hydrogen abstraction or C–C bond-forming reactions. The active photocatalyst is generated from 1,8-dihydroxyanthraquinone by photoinduced single-electron reduction to the radical anion or subsequent protonation and further reduction (or vice versa) to the semiquinone anion. Subsequent visible-light excitation of the anthraquinone radical anion or semiquinone anion converts them into very potent single-electron donors. A plausible mechanism for the reaction is proposed on the basis of control experiments and spectroscopic investigations.
Fil: Bardagi, Javier Ivan. Universitat Regensburg; Alemania. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; Argentina
Fil: Ghosh, Indrajit. Universitat Regensburg; Alemania
Fil: Schmalzbauer, Matthias. Universitat Regensburg; Alemania
Fil: Ghosh, Tamal. Universitat Regensburg; Alemania
Fil: König, Burkhard. Universitat Regensburg; Alemania
Materia
ELECTRON TRANSFER
PHOTOCHEMISTRY
PHOTOREDOX CATALYSIS
QUINONES
RADICAL IONS
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/85336
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/85336
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Anthraquinones as photoredox catalysts for the reductive activation of aryl halidesBardagi, Javier IvanGhosh, IndrajitSchmalzbauer, MatthiasGhosh, TamalKönig, BurkhardELECTRON TRANSFERPHOTOCHEMISTRYPHOTOREDOX CATALYSISQUINONESRADICAL IONShttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Quinones are ubiquitous in nature as structural motifs in natural products and redox mediators in biological electron-transfer processes. Although their oxidation properties have already been used widely in chemical and photochemical reactions, the applications of quinones in reductive photoredox catalysis are less explored. We report the visible-light photoreduction of aryl halides (Ar–X; X = Cl, Br, I) by 1,8-dihydroxyanthraquinone. The resulting aryl radical anions fragment into halide anions and aryl radicals, which react through hydrogen abstraction or C–C bond-forming reactions. The active photocatalyst is generated from 1,8-dihydroxyanthraquinone by photoinduced single-electron reduction to the radical anion or subsequent protonation and further reduction (or vice versa) to the semiquinone anion. Subsequent visible-light excitation of the anthraquinone radical anion or semiquinone anion converts them into very potent single-electron donors. A plausible mechanism for the reaction is proposed on the basis of control experiments and spectroscopic investigations.Fil: Bardagi, Javier Ivan. Universitat Regensburg; Alemania. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; ArgentinaFil: Ghosh, Indrajit. Universitat Regensburg; AlemaniaFil: Schmalzbauer, Matthias. Universitat Regensburg; AlemaniaFil: Ghosh, Tamal. Universitat Regensburg; AlemaniaFil: König, Burkhard. Universitat Regensburg; AlemaniaWiley VCH Verlag2018-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/85336Bardagi, Javier Ivan; Ghosh, Indrajit; Schmalzbauer, Matthias; Ghosh, Tamal; König, Burkhard; Anthraquinones as photoredox catalysts for the reductive activation of aryl halides; Wiley VCH Verlag; European Journal of Organic Chemistry; 2018; 1; 1-2018; 34-401434-193X1099-0690CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1002/ejoc.201701461info:eu-repo/semantics/altIdentifier/url/https://onlinelibrary.wiley.com/doi/full/10.1002/ejoc.201701461info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T10:23:10Zoai:ri.conicet.gov.ar:11336/85336instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982025-09-29 10:23:11.208CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Anthraquinones as photoredox catalysts for the reductive activation of aryl halides
title Anthraquinones as photoredox catalysts for the reductive activation of aryl halides
spellingShingle Anthraquinones as photoredox catalysts for the reductive activation of aryl halides
Bardagi, Javier Ivan
ELECTRON TRANSFER
PHOTOCHEMISTRY
PHOTOREDOX CATALYSIS
QUINONES
RADICAL IONS
title_short Anthraquinones as photoredox catalysts for the reductive activation of aryl halides
title_full Anthraquinones as photoredox catalysts for the reductive activation of aryl halides
title_fullStr Anthraquinones as photoredox catalysts for the reductive activation of aryl halides
title_full_unstemmed Anthraquinones as photoredox catalysts for the reductive activation of aryl halides
title_sort Anthraquinones as photoredox catalysts for the reductive activation of aryl halides
dc.creator.none.fl_str_mv Bardagi, Javier Ivan
Ghosh, Indrajit
Schmalzbauer, Matthias
Ghosh, Tamal
König, Burkhard
author Bardagi, Javier Ivan
author_facet Bardagi, Javier Ivan
Ghosh, Indrajit
Schmalzbauer, Matthias
Ghosh, Tamal
König, Burkhard
author_role author
author2 Ghosh, Indrajit
Schmalzbauer, Matthias
Ghosh, Tamal
König, Burkhard
author2_role author
author
author
author
dc.subject.none.fl_str_mv ELECTRON TRANSFER
PHOTOCHEMISTRY
PHOTOREDOX CATALYSIS
QUINONES
RADICAL IONS
topic ELECTRON TRANSFER
PHOTOCHEMISTRY
PHOTOREDOX CATALYSIS
QUINONES
RADICAL IONS
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv Quinones are ubiquitous in nature as structural motifs in natural products and redox mediators in biological electron-transfer processes. Although their oxidation properties have already been used widely in chemical and photochemical reactions, the applications of quinones in reductive photoredox catalysis are less explored. We report the visible-light photoreduction of aryl halides (Ar–X; X = Cl, Br, I) by 1,8-dihydroxyanthraquinone. The resulting aryl radical anions fragment into halide anions and aryl radicals, which react through hydrogen abstraction or C–C bond-forming reactions. The active photocatalyst is generated from 1,8-dihydroxyanthraquinone by photoinduced single-electron reduction to the radical anion or subsequent protonation and further reduction (or vice versa) to the semiquinone anion. Subsequent visible-light excitation of the anthraquinone radical anion or semiquinone anion converts them into very potent single-electron donors. A plausible mechanism for the reaction is proposed on the basis of control experiments and spectroscopic investigations.
Fil: Bardagi, Javier Ivan. Universitat Regensburg; Alemania. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; Argentina
Fil: Ghosh, Indrajit. Universitat Regensburg; Alemania
Fil: Schmalzbauer, Matthias. Universitat Regensburg; Alemania
Fil: Ghosh, Tamal. Universitat Regensburg; Alemania
Fil: König, Burkhard. Universitat Regensburg; Alemania
description Quinones are ubiquitous in nature as structural motifs in natural products and redox mediators in biological electron-transfer processes. Although their oxidation properties have already been used widely in chemical and photochemical reactions, the applications of quinones in reductive photoredox catalysis are less explored. We report the visible-light photoreduction of aryl halides (Ar–X; X = Cl, Br, I) by 1,8-dihydroxyanthraquinone. The resulting aryl radical anions fragment into halide anions and aryl radicals, which react through hydrogen abstraction or C–C bond-forming reactions. The active photocatalyst is generated from 1,8-dihydroxyanthraquinone by photoinduced single-electron reduction to the radical anion or subsequent protonation and further reduction (or vice versa) to the semiquinone anion. Subsequent visible-light excitation of the anthraquinone radical anion or semiquinone anion converts them into very potent single-electron donors. A plausible mechanism for the reaction is proposed on the basis of control experiments and spectroscopic investigations.
publishDate 2018
dc.date.none.fl_str_mv 2018-01
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
http://purl.org/coar/resource_type/c_6501
info:ar-repo/semantics/articulo
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/11336/85336
Bardagi, Javier Ivan; Ghosh, Indrajit; Schmalzbauer, Matthias; Ghosh, Tamal; König, Burkhard; Anthraquinones as photoredox catalysts for the reductive activation of aryl halides; Wiley VCH Verlag; European Journal of Organic Chemistry; 2018; 1; 1-2018; 34-40
1434-193X
1099-0690
CONICET Digital
CONICET
url http://hdl.handle.net/11336/85336
identifier_str_mv Bardagi, Javier Ivan; Ghosh, Indrajit; Schmalzbauer, Matthias; Ghosh, Tamal; König, Burkhard; Anthraquinones as photoredox catalysts for the reductive activation of aryl halides; Wiley VCH Verlag; European Journal of Organic Chemistry; 2018; 1; 1-2018; 34-40
1434-193X
1099-0690
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1002/ejoc.201701461
info:eu-repo/semantics/altIdentifier/url/https://onlinelibrary.wiley.com/doi/full/10.1002/ejoc.201701461
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
dc.publisher.none.fl_str_mv Wiley VCH Verlag
publisher.none.fl_str_mv Wiley VCH Verlag
dc.source.none.fl_str_mv reponame:CONICET Digital (CONICET)
instname:Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
repository.name.fl_str_mv CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas
repository.mail.fl_str_mv dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar
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score 13.070432

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