Electrosynthesis of Stabilized Diazo Compounds from Hydrazones
Nour Tanbouza, Alessia Petti, Matthew C. Leech, Laurent Caron, Jamie M. Walsh, Kevin Lam, Thierry Ollevier
Abstract
An electrochemical synthesis of diazo compounds from hydrazones in yields as high as 99% was performed. This method was elaborated as a useful synthetic method and demonstrated on various diazo compounds (24 examples). Apart from exhibiting an efficiency that matched that of commonly used harsh and toxic chemical oxidants, this reaction is practically simple to set up, requires mild conditions, and is highly electron efficient (3 F/mol).
Topics & Concepts
DiazoElectrosynthesisChemistryCombinatorial chemistryElectrochemistryReaction conditionsOrganic chemistryPhysical chemistryCatalysisElectrodeCyclopropane Reaction MechanismsCatalytic C–H Functionalization MethodsOxidative Organic Chemistry Reactions