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Visible light-induced direct α C–H functionalization of alcohols

Considering the synthetic value of introducing active alcoholic hydroxyl group, developing C–H functionalization of alcohols is of significance. Herein, we present a photochemical method that under visible light irradiation, selectfluor can effectively promote the oxidative cross-coupling between al...

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Detalles Bibliográficos
Autores principales: Niu, Linbin, Liu, Jiamei, Liang, Xing-An, Wang, Shengchun, Lei, Aiwen
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Nature Publishing Group UK 2019
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6349847/
https://www.ncbi.nlm.nih.gov/pubmed/30692540
http://dx.doi.org/10.1038/s41467-019-08413-9
Descripción
Sumario:Considering the synthetic value of introducing active alcoholic hydroxyl group, developing C–H functionalization of alcohols is of significance. Herein, we present a photochemical method that under visible light irradiation, selectfluor can effectively promote the oxidative cross-coupling between alcohols and heteroarenes without the external photocatalysis, achieving the selective α sp(3) C–H arylation of alcohol, even in the presence of ether. The N-F activation of selectfluor under blue LEDs irradiation is evidenced by electron paramagnetic resonance (EPR) study, which is the key process for the oxidative activation of α sp(3) C–H alcohols. The observed reactivity may have significant implications for chemical transformations.