Site-Selective Electrochemical Oxidation of Glycosides
Marios Kidonakis, Augustin Villotet, Martin D. Witte, Sebastian B. Beil, Adriaan J. Minnaard
Abstract
Quinuclidine-mediated electrochemical oxidation of glycopyranosides provides C3-ketosaccharides with high selectivity and good yields. The method is a versatile alternative to Pd-catalyzed or photochemical oxidation and is complementary to the 2,2,6,6-tetramethylpiperidine 1-oxyl (TEMPO)-mediated C6-selective oxidation. Contrary to the electrochemical oxidation of methylene and methine groups, the reaction proceeds without oxygen.
Topics & Concepts
ChemistryQuinuclidineElectrochemistrySelectivityCatalysisRedoxPhotochemistryMethyleneOxygenGlycosideOrganic chemistryCombinatorial chemistryElectrodePhysical chemistryOxidative Organic Chemistry ReactionsRadical Photochemical ReactionsElectrocatalysts for Energy Conversion