Photoredox-Catalyzed Tandem Radical Cyclization/Hydroxylation for the Synthesis of 4-Hydroxyalkyl-3,3-difluoro-γ-lactams

The photoredox-catalyzed radical difluoroalkylation/ cyclization/hydroxylation cascade reaction of various 2-bromo-2,2-difluoro-N-arylacetamides containing unactivated alkene moieties has been developed, providing green and efficient access to various 4-hydroxyalkyl-3,3-difluoro-gamma-lactams. Control experiments confirmed a radical process, and inexpensive air acted as the sole hydroxy resource. In addition, the highlights of this protocol include good tolerance for a variety functional groups, lower photocatalyst loading, and ease of operation.

Automated summary

In this study, a photoredox-catalyzed radical cascade reaction was developed for the efficient synthesis of 4-hydroxyalkyl-3,3-difluoro-gamma-lactams. The reaction demonstrated good tolerance towards various functional groups, required lower photocatalyst loading, and was easy to perform.