Metal‐Free Electrochemical Coupling of Vinyl Azides: Synthesis of Phenanthridines and <i>β</i>‐Ketosulfones
Guodong Li, Xianqiang Kong, Liang Qi, Long Lin, Ke Yu, Bo Xu, Qianjin Chen
Abstract
We reported an efficient and environmentally benign electrochemical synthesis of phenanthridines by oxidative coupling of vinyl azides with sodium azide or benzenesulfonyl hydrazides, for the first time. The reaction conditions are mild, and no additional metal‐catalyst or exogenous oxidants are needed. The protocol has broad substrate scope and high functional group tolerance. Furthermore, this green electrochemical procedure can be readily extended to the synthesis of β ‐ketosulfones. Gram scale reactions further demonstrate the practicability.
Topics & Concepts
ChemistrySodium azideElectrochemistryCatalysisCombinatorial chemistrySubstrate (aquarium)AzideFunctional groupMetalOrganic chemistryElectrodeOceanographyPhysical chemistryGeologyPolymerSulfur-Based Synthesis TechniquesRadical Photochemical ReactionsCatalytic C–H Functionalization Methods