Oxidative Coupling of 4-Hydroxycoumarins with Quinoxalin-2(1H)-ones Induced by Visible Light under Aerobic Conditions
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Título: | Oxidative Coupling of 4-Hydroxycoumarins with Quinoxalin-2(1H)-ones Induced by Visible Light under Aerobic Conditions |
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Autor/es: | Laze, Loris | Romero, Paula | Bosque, Irene | Gonzalez-Gomez, Jose C. |
Grupo/s de investigación o GITE: | Nuevos Materiales y Catalizadores (MATCAT) |
Centro, Departamento o Servicio: | Universidad de Alicante. Departamento de Química Orgánica | Universidad de Alicante. Instituto Universitario de Síntesis Orgánica |
Palabras clave: | Oxidative coupling | 4-hydroxycoumarins | Quinoxalin-2(1H)-ones | Sustainable chemistry | Photocatalysis |
Fecha de publicación: | 23-dic-2022 |
Editor: | Wiley-VCH GmbH |
Cita bibliográfica: | European Journal of Organic Chemistry. 2023, 26(6): e202201484. https://doi.org/10.1002/ejoc.202201484 |
Resumen: | 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. |
Patrocinador/es: | 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.). |
URI: | http://hdl.handle.net/10045/130932 |
ISSN: | 1434-193X (Print) | 1099-0690 (Online) |
DOI: | 10.1002/ejoc.202201484 |
Idioma: | eng |
Tipo: | info:eu-repo/semantics/article |
Derechos: | © 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. |
Revisión científica: | si |
Versión del editor: | https://doi.org/10.1002/ejoc.202201484 |
Aparece en las colecciones: | INV - MATCAT - Artículos de Revistas |
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