Photoredox-Catalyzed Radical-Addition/Hemiaminalization Cascade of Cinnamaldehyde: Modular Access to Difluoro-5-hydroxypyrrolidinone

Abstract

A new photoredox-catalyzed cascade was accomplished by taking advantage of the bifunctional reactivity of bromodifluoroacetamide with cinnamaldehydes, enabling rapid construction of structurally diverse and highly functionalized difluoro-5-hydroxypyrrolidin-2-ones with excellent chemo- and regio-selectivity. Notably, this transformation proceeds a well-designed tandem process involving sequential regioselective radical addition and challenging hemiaminalization. This strategy provides an innovative modular approach to assemble rarely accessed difluoro-γ-hemiaminal heterocyclic scaffolds, which would facilitate further exploration of their pharmaceutical applications.