期刊
SYNTHESIS-STUTTGART
卷 44, 期 8, 页码 1183-1189出版社
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0031-1290579
关键词
hypervalent iodine; active reagent; quinones; oxidation; phenols
资金
- JSPS
- MEXT
- Ritsumeikan Global Innovation Research Organization (R-GIRO)
- Asahi Glass Foundation
- NEDO of Japan
- Grants-in-Aid for Scientific Research [24689002, 23390005, 21249002] Funding Source: KAKEN
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).
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