Hidden Reactivity of Barbituric and Meldrum’s Acids: Atom-Efficient Free-Radical C–O Coupling with N-Hydroxy Compounds

Abstract

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.

Key words

radicals - oxidative coupling - NHPI - barbituric acids - Meldrum’s acids

Publication History

Received: 26 July 2021

Accepted after revision: 13 September 2021

Accepted Manuscript online:
13 September 2021

Article published online:
19 October 2021

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