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

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

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...

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Veröffentlicht in:Organic letters 2023-07, Vol.25 (26), p.4898-4902
Hauptverfasser: Dang-Nguyen, Ashley, Legaspi, Kristine C., McCarty, Connor T., Smith, Diane K., Gustafson, Jeffrey
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container_end_page 4902
container_issue 26
container_start_page 4898
container_title Organic letters
container_volume 25
creator Dang-Nguyen, Ashley
Legaspi, Kristine C.
McCarty, Connor T.
Smith, Diane K.
Gustafson, Jeffrey
description 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.
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title A Light-Promoted Innate Trifluoromethylation of Pyridones and Related N‑Heteroarenes
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