Palladium-Catalyzed N-Fluoroallylation of Sulfoximines and Benzophenone Imine with gem-Difluorinated Cyclopropanes.

Abstract

Sulfoximines are indispensable core scaffolds in medicinal chemistry and organic synthesis. N-Allylation represents a powerful strategy for enriching the structural diversity of sulfoximines, while fluorine incorporation can effectively enhance the lipophilicity and metabolic stability of functional molecules. Herein, we disclose an efficient Pd-catalyzed N-fluoroallylation of sulfoximines using gem-difluorinated cyclopropylamines. This transformation is enabled by sequential C-C bond activation and C-F bond cleavage, affording a series of N-fluoroallylic sulfoximines bearing monofluoroalkene motifs with excellent Z-stereoselectivity. This protocol features mild reaction conditions and broad substrate compatibility, providing a novel and practical platform for the construction of fluorinated sulfoximine derivatives.