A Light-Promoted Innate Trifluoromethylation of Pyridones and Related <i>N</i>-Heteroarenes
Ashley Dang-Nguyen, Kristine Legaspi, Connor T. McCarty, Diane K. Smith, Jeffrey L. Gustafson
Abstract
High Resolution Image Download MS PowerPoint Slide 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.
Topics & Concepts
ChemistryTrifluoromethylationCombinatorial chemistryOrganic chemistryTrifluoromethylAlkylFluorine in Organic ChemistryInorganic Fluorides and Related CompoundsRadical Photochemical Reactions