Visible-Light-Enabled Ph<sub>3</sub>P/LiI-Promoted Tandem Radical Trifluoromethylation/Cyclization/Iodination of 1,6-Enynes with Togni’s Reagent
Hui Liu, Xu Fan, Jinkai Hu, Tongtong Ma, Feng Wang, Jinhui Yang, Dianjun Li
Abstract
We report the visible-light-induced Ph3P/LiI-promoted intermolecular cascade trifluoromethyl radical addition/5-exo-dig cyclization/iodination of 1,6-enynes with Togni’s reagent using LiI as the iodine source without the need of the transition metal, oxidant, and base. This reaction promises to be a useful method for the preparation of trifluoromethyl-substituted and vinyl C–I bond-containing pyrrolidines and benzofuran products with good regioselectivity and functional-group tolerance under ambient conditions.
Topics & Concepts
ChemistryTrifluoromethylationReagentRegioselectivityHalogenationTrifluoromethylTandemIodineBenzofuranFunctional groupIntermolecular forceSulfonylMedicinal chemistryPhotochemistryCombinatorial chemistryOrganic chemistryCatalysisMoleculeAlkylMaterials scienceComposite materialPolymerFluorine in Organic ChemistryRadical Photochemical ReactionsCatalytic C–H Functionalization Methods