Journal
SYNTHESIS-STUTTGART
Volume 54, Issue 2, Pages 506-516Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/a-1643-7642
Keywords
radicals; oxidative coupling; NHPI; barbituric acids; Meldrum's acids
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Funding
- Russian Foundation for Basic Research [20-33-70109]
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The reactivity of CH-acidic and structurally related enol-containing heterocycles towards N-oxyl radicals was investigated, showing high affinity between these substrates. Highly selective and efficient N-oxyl radical mediated C-O coupling of substituted barbituric or Meldrum's acids with N-hydroxy compounds was achieved using inexpensive manganese-containing salts as oxidants. Metal-free C-O coupling was demonstrated using diacetyliminoxyl as both the oxidant and the coupling partner.
The 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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