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Photoredox catalysis powered by triplet fusion upconversion: arylation of heteroarenes

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Photoredox catalysis powered by triplet fusion upconversion: arylation of heteroarenes

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dc.contributor.author Castellanos-Soriano, Jorge es_ES
dc.contributor.author Álvarez-Gutiérrez, Daniel es_ES
dc.contributor.author Jiménez Molero, María Consuelo es_ES
dc.contributor.author Pérez-Ruiz, Raúl es_ES
dc.date.accessioned 2023-10-05T18:02:04Z
dc.date.available 2023-10-05T18:02:04Z
dc.date.issued 2022-07 es_ES
dc.identifier.issn 1474-905X es_ES
dc.identifier.uri http://hdl.handle.net/10251/197779
dc.description.abstract [EN] In this work, the feasibility of triplet fusion upconversion (TFU, also named triplet-triplet annihilation upconversion) technology for the functionalization (arylation) of furans and thiophenes has been successfully proven. Activation of aryl halides by TFU leads to generation of aryl radical intermediates; trapping of the latter by the corresponding heteroarenes, which act as nucleophiles, affords the final coupling products. Advantages of this photoredox catalytic method include the use of very mild conditions (visible light, standard conditions), employment of commercially available reactants and low-loading metal-free photocatalysts, absence of any sacrificial agent (additive) in the medium and short irradiation times. The involvement of the high energetic delayed fluorescence in the reaction mechanism has been evidenced by quenching studies, whereas the two-photon nature of this photoredox arylation of furans and thiophenes has been manifested by the dependence on the energy source power. Finally, the scaling-up conditions have been gratifyingly afforded by a continuous-flow device. es_ES
dc.description.sponsorship We thank the Generalitat Valenciana (project CIDEGENT/2018/044) and the Spanish Government (project PID2019-105391GB-C22 funded by MCIN/AEI/10.13039/501100011033 and fellowship PRE2020-093783 funded by MCIN/AEI/10.13039/501100011033) for financial support. We also thank Prof. Julia Perez-Prieto for spectroscopy facilities. es_ES
dc.language Inglés es_ES
dc.publisher The Royal Society of Chemistry es_ES
dc.relation.ispartof Photochemical & Photobiological Sciences es_ES
dc.rights Reconocimiento (by) es_ES
dc.subject Visible light es_ES
dc.subject Photoredox catalysis es_ES
dc.subject Arylations es_ES
dc.subject Furans es_ES
dc.subject Thiophenes es_ES
dc.subject Photon upconversion es_ES
dc.subject Triplet fusion (triplet-triplet annihilation) es_ES
dc.subject.classification QUIMICA ORGANICA es_ES
dc.title Photoredox catalysis powered by triplet fusion upconversion: arylation of heteroarenes es_ES
dc.type Artículo es_ES
dc.identifier.doi 10.1007/s43630-022-00203-5 es_ES
dc.relation.projectID info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/PID2019-105391GB-C22/ES/DESARROLLO DE NUEVOS SISTEMAS DE CONVERSION BIFOTONICA A MAYOR FRECUENCIA BASADOS EN ANIQUILACION TRIPLETE-TRIPLETE PARA FOTOCATALISIS REDOX CON LUZ VISIBLE/ es_ES
dc.relation.projectID info:eu-repo/grantAgreement/GENERALITAT VALENCIANA//CIDEGENT%2F2018%2F044//PHOTON UPCONVERSION REDOX CATALYSIS/ es_ES
dc.relation.projectID info:eu-repo/grantAgreement/MICINN//PRE2020-093783/ es_ES
dc.rights.accessRights Abierto es_ES
dc.contributor.affiliation Universitat Politècnica de València. Instituto Universitario Mixto de Biología Molecular y Celular de Plantas - Institut Universitari Mixt de Biologia Molecular i Cel·lular de Plantes es_ES
dc.contributor.affiliation Universitat Politècnica de València. Escuela Técnica Superior de Ingenieros Industriales - Escola Tècnica Superior d'Enginyers Industrials es_ES
dc.contributor.affiliation Universitat Politècnica de València. Departamento de Química - Departament de Química es_ES
dc.description.bibliographicCitation Castellanos-Soriano, J.; Álvarez-Gutiérrez, D.; Jiménez Molero, MC.; Pérez-Ruiz, R. (2022). Photoredox catalysis powered by triplet fusion upconversion: arylation of heteroarenes. Photochemical & Photobiological Sciences. 21(7):1175-1184. https://doi.org/10.1007/s43630-022-00203-5 es_ES
dc.description.accrualMethod S es_ES
dc.relation.publisherversion https://doi.org/10.1007/s43630-022-00203-5 es_ES
dc.description.upvformatpinicio 1175 es_ES
dc.description.upvformatpfin 1184 es_ES
dc.type.version info:eu-repo/semantics/publishedVersion es_ES
dc.description.volume 21 es_ES
dc.description.issue 7 es_ES
dc.identifier.pmid 35303293 es_ES
dc.relation.pasarela S\460343 es_ES
dc.contributor.funder GENERALITAT VALENCIANA es_ES
dc.contributor.funder AGENCIA ESTATAL DE INVESTIGACION es_ES
dc.contributor.funder Ministerio de Ciencia e Innovación es_ES
dc.contributor.funder Universitat Politècnica de València es_ES
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