Regioselective Synthesis of <i>N</i><sup>2</sup>-Aryl 1,2,3-Triazoles via Electro-oxidative Coupling of Enamines and Aryldiazonium Salts
Mrinmay Baidya, Samrat Mallick, Suman De Sarkar
Abstract
-aryl 1,2,3-triazoles is reported via sequential C-N bond formation and electro-oxidative N-N coupling under metal-free conditions. Readily accessible 2-aminoacrylates and aryldiazonium salts were used as starting materials, and the developed protocol displays excellent functional group tolerance, allowing an extensive range of substrate scope up to 91% isolated yield. Various mechanistic studies, along with the isolation of an intermediate adduct, refer to successive ionic and radical reaction sequences.
Topics & Concepts
ChemistryRegioselectivityAdductArylYield (engineering)Functional groupCombinatorial chemistrySubstrate (aquarium)RadicalOxidative coupling of methaneIonic bondingOxidative additionOxidative phosphorylationMedicinal chemistryOrganic chemistryCatalysisIonAlkylPolymerMaterials scienceOceanographyBiochemistryMetallurgyGeologyRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsSulfur-Based Synthesis Techniques