Photocatalytic C–H functionalization of enamides with N-allylbromodifluoroacetamides via difluoroamidoalkylation and difluoroamidosulfonylation

Abstract

Starting from enamides and N-allylbromodifluoroacetamides, two distinct photocatalyzed cyclization/functionalization strategies have been devised to efficiently introduce a 3,3-difluoro-γ-lactam unit into trifunctionalized enamides. Through these approaches, a collection of 38 trisubstituted amides bearing an absolute (E)-configuration was synthesized with acceptable yields. The visible-light-driven difluoroamidoalkylation and three-component difluoroamidosulfonylation processes both rely on two fundamental mechanisms: intramolecular radical relay and subsequent intermolecular radical interaction. These photocatalytic transformations are characterized by their broad substrate applicability, remarkable compatibility with diverse functional groups, mild reaction conditions, and exceptional regio- and stereoselectivity.

Graphical abstract: Photocatalytic C–H functionalization of enamides with N-allylbromodifluoroacetamides via difluoroamidoalkylation and difluoroamidosulfonylation

Supplementary files

Article information

Article type
Research Article
Submitted
16 May 2025
Accepted
04 Jul 2025
First published
04 Jul 2025

Org. Chem. Front., 2025, Advance Article

Photocatalytic C–H functionalization of enamides with N-allylbromodifluoroacetamides via difluoroamidoalkylation and difluoroamidosulfonylation

Y. Wang, X. Zou, P. Xu, D. Chen, Y. Zhang, S. Yan and H. Zuo, Org. Chem. Front., 2025, Advance Article , DOI: 10.1039/D5QO00764J

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