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A Light-Promoted Innate Trifluoromethylation of Pyridones and Related N-Heteroarenes

[Image: see text] We report a practical, light-mediated perfluoroalkylation using Langlois’ reagent (sodium trifluoromethylsulfinate) that proceeds in the absence of any photocatalyst or additives. This method has allowed for the facile functionalization of pyridones and related N-heteroarenes such...

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Detalles Bibliográficos
Autores principales: Dang-Nguyen, Ashley, Legaspi, Kristine C., McCarty, Connor T., Smith, Diane K., Gustafson, Jeffrey
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10334463/
https://www.ncbi.nlm.nih.gov/pubmed/37377204
http://dx.doi.org/10.1021/acs.orglett.3c01710
Descripción
Sumario:[Image: see text] We report a practical, light-mediated perfluoroalkylation using Langlois’ reagent (sodium trifluoromethylsulfinate) that proceeds in the absence of any photocatalyst or additives. This method has allowed for the facile functionalization of pyridones and related N-heteroarenes such as azaindole. This protocol is operationally simple, uses readily available materials, and is tolerable for electron-neutral and -rich functional pyridones. Cyclic voltammetry was utilized as a mechanistic probe, and preliminary data suggest the reaction may involve an electrophilic radical mechanism.