Iron-Catalyzed Oxidative Cyclization of 2-Amino Styrenes with Alcohols and Methyl Arenes for the Synthesis of Polysubstituted Quinolines
Seok Beom Lee, Simin Chun, Seung Hyun Choi, Junhwa Hong, Dong‐Chan Oh, Suckchang Hong
Abstract
Herein, we present the iron-catalyzed oxidative cyclization of alcohol/methyl arene with 2-amino styrene to synthesize polysubstituted quinoline. Low-oxidation level substrates such as alcohols and methyl arenes are converted to aldehydes in the presence of an iron catalyst and di- t -butyl peroxide. Then, the quinoline scaffold is synthesized through imine condensation/radical cyclization/oxidative aromatization. Our protocol showed a broad substrate scope, and various functionalization and fluorescence applications of quinoline products demonstrated its synthetic ability.
Topics & Concepts
ChemistryQuinolineCatalysisAromatizationSubstrate (aquarium)AnilineOxidative phosphorylationStyreneOrganic chemistryIminePeroxideCombinatorial chemistryPolymerCopolymerOceanographyBiochemistryGeologyCatalytic C–H Functionalization MethodsRadical Photochemical ReactionsSulfur-Based Synthesis Techniques