Visible‐Light‐Mediated Cycloaddition of Azobenzenes and Nonstabilized Azomethine Ylides to Access 1,2,4‐Triazolidines
Jingya Yang, Wentong Ma, Sheng-Yu Wang, Jiangjiang Li, Hongyan Zhou
Abstract
Abstract A visible‐light‐mediated cycloaddition of azobenzenes and nonstabilized azomethine ylides has been developed to access 1,2,4‐triazolidines. With readily available organic dye rose bengal as a photocatalyst and alkyl tertiary amines as precursors for azomethine ylides, the reaction proceeded smoothly under visible light irradiation at room temperature, affording various 4‐alkyl‐1,2‐diaryl‐1,2,4‐triazolidines with yields of up to 96%. Preliminarily mechanistic studies suggest that the nonstabilized azomethine ylides are formed in situ through photoredox catalysis.
Topics & Concepts
ChemistryCycloadditionVisible spectrumAzomethine ylideRose bengalPhotochemistryAlkylCatalysisAzobenzeneMedicinal chemistryOrganic chemistry1,3-Dipolar cycloadditionMoleculeOptoelectronicsPhysicsRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsSulfur-Based Synthesis Techniques