Selective Toluene Electrooxidation to Benzyl Alcohol
Madeleine K. Wilsey, Nathalia Cajiao, Aleksa Radović, Michael L. Neidig, Yasemin Basdogan, Astrid M. Müller
Abstract
OH radicals to form methanesulfinic acid, limiting benzyl alcohol generation. The wet organic solvent environment additionally prevented overoxidation beyond the alcohol by stabilizing radical intermediates through hydrogen bonding networks, effectively arresting the reaction after the first oxygenation. Likewise, benzyl alcohol oxidation yielded benzaldehyde, with no overoxidation to benzoic acid. Our findings establish fundamental design principles for selective hydrocarbon oxidations by leveraging solvent-mediated interactions, with broad implications for sustainable chemical synthesis.
Topics & Concepts
ChemistryBenzyl alcoholTolueneRadicalPhotochemistrySolventHydrogen peroxideAlcoholAlcohol oxidationCatalysisProtonationSelectivityOrganic chemistryOxygenHydrogen bondHydrocarbonDeoxygenationMoleculeAqueous solutionInorganic chemistryHydrogenRedoxHydroxyl radicalElectrochemical Analysis and ApplicationsElectrocatalysts for Energy ConversionCatalysis and Oxidation Reactions