Electrochemical, Iodine-Mediated α-CH Amination of Ketones by Umpolung of Silyl Enol Ethers
Julia Strehl, Gerhard Hilt
Abstract
The electrochemical, oxidative Umpolung reaction of silyl enol ethers utilizing simple iodide salts for the synthesis of α-amino ketones is described. The products were isolated in excellent yields of up to 100%, and various functionalized starting materials were accepted in an undivided electrochemical cell design. Moreover, a sensitivity assessment to ensure an improved reproducibility of the reaction and cyclic voltammetry experiments were performed to postulate a plausible reaction mechanism on their basis.
Topics & Concepts
UmpolungChemistrySilylationEnolAminationElectrochemistryIodineReactivity (psychology)IodideAmmoniaOrganic chemistryCyclic voltammetryEnol etherCombinatorial chemistryCatalysisNucleophileElectrodePhysical chemistryAlternative medicineMedicinePathologyOxidative Organic Chemistry ReactionsRadical Photochemical ReactionsCatalytic C–H Functionalization Methods