Photocatalytic Cyclization/Defluorination Domino Sequence to Access 3-Fluoro-1,5-dihydro-2<i>H</i>-pyrrol-2-one Scaffold
Zhipeng Ye, Yuan‐Zhuo Hu, Jianping Guan, Kai Chen, Fang Liu, Jie Gao, Jun‐An Xiao, Hao‐Yue Xiang, Xiaoqing Chen, Hua Yang
Abstract
We herein report an unprecedented photoinduced cyclization/defluorination domino process of N-allylbromodifluoroacetamide with cyclic secondary amines. Consequently, a wide array of valuable 3-fluoro-1,5-dihydro-2H-pyrrol-2-ones were facilely prepared from readily available starting materials under mild conditions. Preliminary mechanistic investigations suggest that a radical chain propagation and amine-promoted defluorination pathway are presumably involved in this transformation.
Topics & Concepts
ChemistryDominoAmine gas treatingScaffoldCombinatorial chemistryPhotocatalysisCyclic aminesSequence (biology)Cascade reactionTransformation (genetics)PhotochemistryOrganic chemistryCatalysisBiochemistryGeneMedicineBiomedical engineeringFluorine in Organic ChemistryCatalytic C–H Functionalization MethodsCyclopropane Reaction Mechanisms