Redox‐Neutral Selenium‐Catalysed Isomerisation of <i>para</i> ‐Hydroxamic Acids into <i>para</i> ‐Aminophenols
Hsiang‐Yu Chuang, Manuel Schupp, Ricardo Meyrelles, Boris Maryasin, Nuno Maulide
Abstract
Abstract A selenium‐catalysed para ‐hydroxylation of N ‐aryl‐hydroxamic acids is reported. Mechanistically, the reaction comprises an N−O bond cleavage and consecutive selenium‐induced [2,3]‐rearrangement to deliver para ‐hydroxyaniline derivatives. The mechanism is studied through both 18 O‐crossover experiments as well as quantum chemical calculations. This redox‐neutral transformation provides an unconventional synthetic approach to para ‐aminophenols.
Topics & Concepts
ChemistryIsomerizationSeleniumRedoxHydroxylationQuantum chemicalBond cleavageMedicinal chemistryAutocatalysisHydroxamic acidStereochemistryCatalysisMoleculeOrganic chemistryEnzymeOrganoselenium and organotellurium chemistryCatalytic C–H Functionalization MethodsSulfur-Based Synthesis Techniques