Nickel-Catalyzed Cross-Electrophile Ring Opening/gem-Difluoroallylation of Aziridines

Hereinwe report a nickel-catalyzed regioselective cross-electrophilering opening reaction of sulfonyl-protected aziridines with trifluoromethyl-substitutedalkenes as the gem-difluoroallylating agents, providinga new and efficient entry to prepare gem-difluorobishomoallylicsulfonamides. Moreover, the scaffold of 6-fluoro-1,2,3,4-tetrahydropyridinecan be constructed starting from the ring opening products via NaH-mediatedintramolecular defluorinative nucleophilic vinylic substitution.

Automated summary

A nickel-catalyzed regioselective cross-electrophilic ring opening reaction of sulfonyl-protected aziridines with trifluoromethyl-substituted alkenes has been reported, 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.