Photoredox-Catalyzed Tandem Radical Cyclization/Hydroxylation for the Synthesis of 4-Hydroxyalkyl-3,3-difluoro-γ-lactams
Bin Sun, Xiaohui Zhuang, Jieli Yin, Kesheng Zhang, Haiyun Zhao, Can Jin
Abstract
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-γ-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.
Topics & Concepts
HydroxylationPhotoredox catalysisCatalysisAlkeneChemistryTandemCombinatorial chemistryCascade reactionRadical cyclizationPhotocatalysisOrganic chemistryEnzymeMaterials scienceComposite materialFluorine in Organic ChemistryRadical Photochemical ReactionsCatalytic C–H Functionalization Methods