μ-Oxo-Bridged Hypervalent Iodine(III) Compound as an Extreme Oxidant for Aqueous Oxidations

Abstract

We have found that in aqueous oxidations the μ-oxo-bridged hypervalent iodine trifluoroacetate reagent 1 {[(PhI(OCOCF₃)]₂O} is generally more reactive than the corresponding monomeric reagent, especially toward phenolic substrates. μ-Oxo-bridged 1 in aqueous media thus provided dearomatized quinones 3 in excellent yields in most cases compared to conventional phenyliodine(III) diacetate and bis(trifluoroacetate), as a result of the rapid oxidation of both phenols and naphthols 2. Furthermore, the oxidation reactions proceeded even in water using water-soluble μ-oxo oxidant 1, which has promise for μ-oxo-bridged reagent 1 to become the favored reagent over hydrophobic phenyliodine(III) diacetate and bis(trifluoroacetate).

Key words

hypervalent iodine - active reagent - quinones - oxidation - phenols

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