Nickel-Catalyzed Cross-Electrophile Ring Opening/<i>gem</i>-Difluoroallylation of Aziridines
Wei Tang, Pei Fan
Abstract
Herein we report a nickel-catalyzed regioselective cross-electrophile ring opening reaction of sulfonyl-protected aziridines with trifluoromethyl-substituted alkenes as the gem -difluoroallylating agents, providing a new and efficient entry to prepare gem -difluorobishomoallylic sulfonamides. Moreover, the scaffold of 6-fluoro-1,2,3,4-tetrahydropyridine can be constructed starting from the ring opening products via NaH-mediated intramolecular defluorinative nucleophilic vinylic substitution.
Topics & Concepts
ChemistryRegioselectivityElectrophileIntramolecular forceRing (chemistry)NucleophileCatalysisSulfonylNickelCombinatorial chemistryHydroaminationMedicinal chemistryStereochemistryOrganic chemistryAlkylFluorine in Organic ChemistrySynthesis and Catalytic ReactionsCatalytic C–H Functionalization Methods