Electrochemically Enabled Intramolecular Aminooxygenation of Alkynes <i>via</i> Amidyl Radical Cyclization
Zhong‐Wei Hou, Hai‐Chao Xu
Abstract
Summary of main observation and conclusion An electrochemical synthesis of oxazol‐2‐ones and imidazol‐2‐ones has been developed via 5‐ exo ‐ dig cyclization of propargylic carbamates‐ and ureas‐derived amidyl radicals. The electrosynthesis relies on the dual function of 2,2,6,6‐tetramethylpiperidin‐ 1‐yl)oxyl (TEMPO) as a redox mediator for amidyl radical formation and an oxygen atom donor. The reactions are conducted under mild conditions using a simple setup and provide convenient access to functionalized oxazol‐2‐ones and imidazol‐2‐ones from readily available materials.
Topics & Concepts
ChemistryElectrosynthesisRadicalIntramolecular forceElectrochemistryCombinatorial chemistryRedoxOxygen atomOrganic chemistryMoleculePhysical chemistryElectrodeRadical Photochemical ReactionsSulfur-Based Synthesis TechniquesCatalytic C–H Functionalization Methods