Synthesis of 3‐Halogenated Quinolin‐2‐Ones from <i>N</i>‐Arylpropynamides <i>via</i> Hypervalent Iodine(III)−Mediated Umpolung Process
Xiaoxian Li, Beibei Zhang, Bingyue Zhao, Xiaofan Wang, Lingzhi Xu, Yunfei Du
Abstract
Abstract The selective synthesis of 3‐halogenated quinolin‐2‐ones from N ‐arylpropynamides was realized via umpolung process mediated by phenyliodine(III) diacetate (PIDA) and MX (LiCl, LiBr, CuI). Differing from most previous electrophilic cyclization/halogenation processes that afforded spiro[4,5]trienones, 3‐halogenated quinolin‐2‐ones were obtained through this method with high selectivity. magnified image
Topics & Concepts
UmpolungHypervalent moleculeChemistryElectrophileHalogenationIodineSelectivityMedicinal chemistryCombinatorial chemistryOrganic chemistryStereochemistryCatalysisNucleophileCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling ReactionsOxidative Organic Chemistry Reactions