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

Org Lett. 2023 Jul 7;25(26):4898-4902. doi: 10.1021/acs.orglett.3c01710. Epub 2023 Jun 28.

Abstract

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.