Oxidative Coupling of 4-Hydroxycoumarins with Quinoxalin-2(1H)-ones Induced by Visible Light under Aerobic Conditions
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Campo DC | Valor | Idioma |
---|---|---|
dc.contributor | Nuevos Materiales y Catalizadores (MATCAT) | es_ES |
dc.contributor.author | Laze, Loris | - |
dc.contributor.author | Romero, Paula | - |
dc.contributor.author | Bosque, Irene | - |
dc.contributor.author | Gonzalez-Gomez, Jose C. | - |
dc.contributor.other | Universidad de Alicante. Departamento de Química Orgánica | es_ES |
dc.contributor.other | Universidad de Alicante. Instituto Universitario de Síntesis Orgánica | es_ES |
dc.date.accessioned | 2023-01-10T11:47:36Z | - |
dc.date.available | 2023-01-10T11:47:36Z | - |
dc.date.issued | 2022-12-23 | - |
dc.identifier.citation | European Journal of Organic Chemistry. 2023, 26(6): e202201484. https://doi.org/10.1002/ejoc.202201484 | es_ES |
dc.identifier.issn | 1434-193X (Print) | - |
dc.identifier.issn | 1099-0690 (Online) | - |
dc.identifier.uri | http://hdl.handle.net/10045/130932 | - |
dc.description.abstract | Direct and selective C(sp2)-H/C(sp2)-H cross-dehydrogenative coupling has become a promising strategy to increase molecular complexity with a high atom economy. This study describes an efficient and straightforward protocol for the regioselective C3-H/C3-H cross-coupling of 4-hydroxycoumarin derivatives with quinoxalin-2(1H)-ones, including late-stage modification of natural drugs, promoted by visible light under aerobic conditions at room temperature. With this approach, a wide range of hybrid drug-like molecules were prepared, using air as the terminal oxidant. Remarkably, the C4 OH group at the coumarin ring is essential for the reaction and has been used as a handle for diverse functionalizations of the final products. Moreover, sunlight can promote the reaction under very mild and sustainable conditions, even on a gram scale. Qualitative and semi-quantitative tools were used to demonstrate the greenness advance of this methodology over previously reported ones. Several experiments were conducted to propose a plausible mechanism for this transformation. | es_ES |
dc.description.sponsorship | This work was financially supported by the Spanish Ministerio de Ciencia e Innovación (grant no. CTQ2017-88171-P), Generalitat Valenciana (SEJIGENT/2021/005, granted to I. B.), and the University of Alicante (GRE20-03-A granted to I. B.). | es_ES |
dc.language | eng | es_ES |
dc.publisher | Wiley-VCH GmbH | es_ES |
dc.rights | © 2022 The Authors. European Journal of Organic Chemistry published by Wiley-VCH GmbH. This is an open access article under the terms of the Creative Commons Attribution-NonCommercial-NoDerivs License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non-commercial and no modifications or adaptations are made. | es_ES |
dc.subject | Oxidative coupling | es_ES |
dc.subject | 4-hydroxycoumarins | es_ES |
dc.subject | Quinoxalin-2(1H)-ones | es_ES |
dc.subject | Sustainable chemistry | es_ES |
dc.subject | Photocatalysis | es_ES |
dc.title | Oxidative Coupling of 4-Hydroxycoumarins with Quinoxalin-2(1H)-ones Induced by Visible Light under Aerobic Conditions | es_ES |
dc.type | info:eu-repo/semantics/article | es_ES |
dc.peerreviewed | si | es_ES |
dc.identifier.doi | 10.1002/ejoc.202201484 | - |
dc.relation.publisherversion | https://doi.org/10.1002/ejoc.202201484 | es_ES |
dc.rights.accessRights | info:eu-repo/semantics/openAccess | es_ES |
dc.relation.projectID | info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/CTQ2017-88171-P | es_ES |
Aparece en las colecciones: | INV - MATCAT - Artículos de Revistas |
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