Tris(4-bromophenyl)aminium Hexachloroantimonate-Initiated Oxidative Povarov-Type Reaction between Glycine Esters and (Cyclopropylidenemethyl)benzenes Using the Counterion as a Chlorine Donor
Yuan Yuan, Yuan Yuan, Shuwei Zhang, Zheng Sun, Yichun Su, Qiyuan Ma, Yu Yuan, Yu Yuan, Xiaodong Jia
Abstract
A tris(4-bromophenyl)aminium hexachloroantimonate-initiated oxidative Povarov-type reaction between glycines and methylenecyclopropanes was realized in the presence of dioxygen, in which the counterion, SbCl6–, served as a chlorine atom donor, enabling the synthesis of a series of chlorinated quinolines in high yields. The mechanistic study showed that the chlorination step might be related to antimony chloride via a radical chlorine atom transfer.
Topics & Concepts
ChemistryCounterionChlorineTrisChlorideMedicinal chemistryChlorine atomOxidative phosphorylationPhotochemistryIonOrganic chemistryBiochemistryCatalytic C–H Functionalization MethodsCyclopropane Reaction MechanismsOxidative Organic Chemistry Reactions