Metal‐Free Organoselenium‐Enabled Radical Relay Azidation‐Carbocyclization
Xin Wang, Sa Guo, Yan Zhang, Zhiguo Zhang, Guisheng Zhang, Yong Ye, Kai Sun
Abstract
Abstract An organoselenium‐enabled radical relay Azidation‐carbocyclization reaction for the preparation of azide‐substituted quinoline‐2,4‐diones was developed. A series of previously unknown structurally diverse azide‐ substituted quinoline‐2,4‐diones were obtained under metal‐free and room‐temperature conditions. The key features of this reaction are a broad substrate scope, amenability to gram‐scale synthesis, and easy product derivatization. Preliminary mechanistic studies support participation of an organoselenium species in a radical relay pathway. magnified image
Topics & Concepts
ChemistryQuinolineAzideDerivatizationCombinatorial chemistryRelayRadicalSubstrate (aquarium)Scope (computer science)Organic chemistryPhotochemistryGeologyPhysicsComputer scienceHigh-performance liquid chromatographyOceanographyQuantum mechanicsPower (physics)Programming languageCatalytic C–H Functionalization MethodsRadical Photochemical ReactionsSulfur-Based Synthesis Techniques