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

Toshifumi Dohi; Tomofumi Nakae; Naoko Takenaga; Teruyoshi Uchiyama; Kei-ichiro Fukushima; Hiromichi Fujioka; Yasuyuki Kita

doi:10.1055/s-0031-1290579

Synthesis, Inhaltsverzeichnis

Synthesis 2012; 44(8): 1183-1189
DOI: 10.1055/s-0031-1290579

special topic

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

Toshifumi Dohi

^aCollege of Pharmaceutical Sciences, Ritsumeikan University, 1-1-1 Nojihigashi, Kusatsu, Shiga, 525-8577, Japan, Fax: +81(77)5615829 eMail: kita@ph.ritsumei.ac.jp

,

Tomofumi Nakae

^aCollege of Pharmaceutical Sciences, Ritsumeikan University, 1-1-1 Nojihigashi, Kusatsu, Shiga, 525-8577, Japan, Fax: +81(77)5615829 eMail: kita@ph.ritsumei.ac.jp

,

Naoko Takenaga

^bGraduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamada-oka, Suita, Osaka, 565-0871, Japan

,

Teruyoshi Uchiyama

^aCollege of Pharmaceutical Sciences, Ritsumeikan University, 1-1-1 Nojihigashi, Kusatsu, Shiga, 525-8577, Japan, Fax: +81(77)5615829 eMail: kita@ph.ritsumei.ac.jp

,

Kei-ichiro Fukushima

^aCollege of Pharmaceutical Sciences, Ritsumeikan University, 1-1-1 Nojihigashi, Kusatsu, Shiga, 525-8577, Japan, Fax: +81(77)5615829 eMail: kita@ph.ritsumei.ac.jp

,

Hiromichi Fujioka

^bGraduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamada-oka, Suita, Osaka, 565-0871, Japan

,

Yasuyuki Kita*

^aCollege of Pharmaceutical Sciences, Ritsumeikan University, 1-1-1 Nojihigashi, Kusatsu, Shiga, 525-8577, Japan, Fax: +81(77)5615829 eMail: kita@ph.ritsumei.ac.jp

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Abstract

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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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Referenzen

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