Por favor, use este identificador para citar o enlazar a este item:
http://hdl.handle.net/10261/269973
COMPARTIR / EXPORTAR:
SHARE CORE BASE | |
Visualizar otros formatos: MARC | Dublin Core | RDF | ORE | MODS | METS | DIDL | DATACITE | |
Título: | Mechanistic Insight into the Light-Triggered CuAAC Reaction: Does Any of the Photocatalyst Go? |
Autor: | Martínez-Haya, R; Heredia, Adrián A.; Castro-Godoy, Willber D.; Schmidt, Luciana C.; Marín, María Luisa CSIC ORCID CVN; Argüello, Juan E. | Fecha de publicación: | 7-abr-2021 | Editor: | ACS Publications | Citación: | Journal of Organic Chemistry 86(8): 5832-5844 (2021) | Resumen: | The attainment of transition-metal catalysis and photoredox catalysis has represented a great challenge over the last years. Herein, we have been able to merge both catalytic processes into what we have called "the light-triggered CuAAC reaction". Particularly, the CuAAC reaction reveals opposite outcomes depending on the nature of the photocatalyst (eosin Y disodium salt and riboflavin tetraacetate) and additives (DABCO, Et3N, and NaN3) employed. To get a better insight into the operating processes, steady-state, time-resolved emission, and laser flash photolysis experiments have been performed to determine reactivity and kinetic data. These results, in agreement with thermodynamic estimations based on reported data, support the proposed mechanisms. While for eosin Y (EY), Cu(II) was reduced by its triplet excited state; for riboflavin tetraacetate (RFTA), mainly triplet excited RFTA state photoreductions by electron donors as additives are mandatory, affording RFTA•- (from DABCO and NaN3) or RFTAH• (from Et3N). Subsequently, these species are responsible for the reduction of Cu(II). For both photocatalysts, photogenerated Cu(I) finally renders 1,2,3-triazole as the final product. The determined kinetic rate constants allowed postulating plausible mechanisms in both cases, bringing to light the importance of kinetic studies to achieve a strong understanding of photoredox processes. | Versión del editor: | http://dx.doi.org/10.1021/acs.joc.1c00272 | URI: | http://hdl.handle.net/10261/269973 | DOI: | 10.1021/acs.joc.1c00272 | Identificadores: | doi: 10.1021/acs.joc.1c00272 issn: 1520-6904 |
Aparece en las colecciones: | (ITQ) Artículos |
Ficheros en este ítem:
Fichero | Descripción | Tamaño | Formato | |
---|---|---|---|---|
accesoRestringido.pdf | 15,38 kB | Adobe PDF | Visualizar/Abrir |
CORE Recommender
SCOPUSTM
Citations
13
checked on 24-abr-2024
WEB OF SCIENCETM
Citations
12
checked on 19-feb-2024
Page view(s)
31
checked on 27-abr-2024
Download(s)
4
checked on 27-abr-2024
Google ScholarTM
Check
Altmetric
Altmetric
NOTA: Los ítems de Digital.CSIC están protegidos por copyright, con todos los derechos reservados, a menos que se indique lo contrario.