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

作者：Dohi Toshifumi; Nakae Tomofumi; Takenaga Naoko; Uchiyama Teruyoshi; Fukushima Kei ichiro; Fujioka Hiromichi; Kita Yasuyuki^*

来源：Synthesis, 2012, 44(8): 1183-1189.

DOI：10.1055/s-0031-1290579

• hypervalent iodine
• active reagent
• quinones
• oxidation
• phenols

We have found that in aqueous oxidations the mu-oxo-bridged hypervalent iodine trifluoroacetate reagent 1 {[(PhI(OCOCF3)](2)O} is generally more reactive than the corresponding monomeric reagent, especially toward phenolic substrates. mu-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 mu-oxo oxidant 1, which has promise for mu-oxo-bridged reagent 1 to become the favored reagent over hydrophobic phenyliodine(III) diacetate and bis(trifluoroacetate).

• 出版日期2012-4