Abstract
AbstractThe reactivity of CH-acidic and structurally related enol-containing heterocycles towards N-oxyl radicals is disclosed. Traditionally, these substrates have been considered as reactants for ionic transformations. Highly selective and efficient N-oxyl radical mediated C–O coupling of substituted barbituric or Meldrum’s acids with N-hydroxy compounds (N-hydroxyimides, hydroxamic acids, oximes, and N-hydroxybenzotriazole) was achieved using inexpensive manganese-containing salts as oxidants. Metal-free C–O coupling was demonstrated using diacetyliminoxyl as both the oxidant (hydrogen-atom acceptor) and the coupling partner.
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