Synthesis · 2012 · 35 citations · 0 references
Advanced Oxidation ProcessEngineeringConventional PhenyliodineOrganic ChemistryChemistryPhenolic SubstratesRedox BiologyAqueous OxidationsExtreme OxidantChemical EngineeringHydrophobic PhenyliodineRedox ChemistryInorganic Chemistryμ-Oxo-bridged Hypervalent IodineDerivativesBiochemistryFluorous SynthesisCatalysisOxygen Reduction ReactionNatural SciencesHalogenation
We have found that in aqueous oxidations the μ-oxo-bridged hypervalent iodine trifluoroacetate reagent <b>1</b> {[(PhI(OCOCF<sub>3</sub>)]<sub>2</sub>O} is generally more reactive than the corresponding monomeric reagent, especially toward phenolic substrates. μ-Oxo-bridged <b>1</b> in aqueous media thus provided dearomatized quinones <b>3</b> 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 <b>2</b>. Furthermore, the oxidation reactions proceeded even in water using water-soluble μ-oxo oxidant <b>1</b>, which has promise for μ-oxo-bridged reagent <b>1</b> to become the favored reagent over hydrophobic phenyliodine(III) diacetate and bis(trifluoroacetate).