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

We report a practical, light-mediated perfluoroalkylationusingLanglois' reagent (sodium trifluoromethylsulfinate) that proceedsin the absence of any photocatalyst or additives. This method hasallowed for the facile functionalization of pyridones and related N-heteroarenes such as azaindole. This protocol is operationallysimple, uses readily available materials, and is tolerable for electron-neutraland -rich functional pyridones. Cyclic voltammetry was utilized asa mechanistic probe, and preliminary data suggest the reaction mayinvolve an electrophilic radical mechanism.

Automated summary

We present a practical, light-mediated perfluoroalkylation method using Langlois' reagent that does not require any photocatalyst or additives. This method allows for easy functionalization of pyridones and related N-heteroarenes such as azaindole. The protocol is straightforward, utilizes readily available materials, and is compatible with both electron-neutral and -rich pyridones.