Functionalization of a Single C−F Bond of Trifluoromethylarenes Assisted by an <i>ortho</i>‐Silyl Group Using a Trityl‐Based All‐in‐One Reagent with Ytterbium Triflate Catalyst
Young‐Chan Kim, Kazuya Kanemoto, Ken Shimomori, Takamitsu Hosoya, Suguru Yoshida
Abstract
Catalytic thiolation and azidation of a single C-F bond of trifluoromethylarenes were achieved assisted by an ortho-silyl group with all-in-one reagents to generate a trityl cation and nucleophiles. The reactions catalyzed by ytterbium triflate efficiently afforded a wide variety of difluoromethylenes avoiding the further C-F bond cleavage, by virtue of the mild conditions without the generation of a Brønsted acid.
Topics & Concepts
TrifluoromethanesulfonateSilylationReagentNucleophileYtterbiumChemistryCatalysisCleavage (geology)Bond cleavageMedicinal chemistryOrganic chemistryCombinatorial chemistryPolymer chemistryMaterials scienceFracture (geology)OptoelectronicsDopingComposite materialFluorine in Organic ChemistryCyclopropane Reaction MechanismsCatalytic C–H Functionalization Methods