Visible‐light‐promoted Radical Cyclization/Arylation Cascade for the Construction of <i>α,</i><scp><i>α</i>‐Difluoro‐<i>γ</i>‐Lactam‐Fused</scp> Quinoxalin‐2(<scp>1<i>H</i></scp>)‐Ones
Yun‐Chao Zhang, Chen Yang, Jing Sun, Jing‐Yun Wang, Mingdong Zhou
Abstract
Comprehensive Summary A visible‐light‐induced tandem radical intramolecular cyclization/arylation of quinoxalin‐2(1 H )‐ones with bromodifluoroacetamides is described. This protocol allows efficient access to a variety of valuable α,α ‐difluoro‐ γ ‐lactam‐fused quinoxalin‐2(1 H )‐ones in moderate to good yields under metal‐free, mild and redox neutral reaction conditions. This strategy is tolerant of various functional groups and a broad range of substrates. The mechanism experiments suggested an involvement of 5‐ exo ‐trig cyclization and a radical process in this transformation.
Topics & Concepts
ChemistryRadical cyclizationTandemIntramolecular forceStereochemistryCascade reactionCascadeLactamRedoxCombinatorial chemistryVisible spectrumMedicinal chemistryCatalysisOrganic chemistryPhysicsChromatographyOptoelectronicsMaterials scienceComposite materialRadical Photochemical ReactionsFluorine in Organic ChemistryCatalytic C–H Functionalization Methods