Access to <i>gem</i>-Difluoro Olefins via C–H Functionalization and Dual Role of Anilines
Zhen Yang, Chao Pei, René M. Koenigs
Abstract
In this Letter, we describe a simple, practical approach in which cheap CuI was used as a catalyst to introduce a gem-difluoro olefin onto simple electron-rich aniline derivatives in good yield via direct C–H functionalization and a subsequent HF elimination reaction. Detailed mechanistic studies point at a dual role of aniline derivatives in this reaction, which serve as a substrate and a basic promoter to trigger the HF elimination step.
Topics & Concepts
AnilineChemistrySurface modificationCombinatorial chemistryYield (engineering)Olefin fiberCatalysisSubstrate (aquarium)Dual roleDual (grammatical number)Organic chemistryOceanographyArtMaterials scienceLiteraturePhysical chemistryGeologyMetallurgyFluorine in Organic ChemistryCatalytic C–H Functionalization MethodsCyclopropane Reaction Mechanisms