Journal
TETRAHEDRON LETTERS
Volume 52, Issue 17, Pages 2212-2215Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2010.12.037
Keywords
Phenolic oxidation; Hypervalent compound; Iodine; Natural product synthesis
Categories
Funding
- Japan Society for the Promotion of Science (JSPS)
- Ministry of Education, Culture, Sports, Science and Technology (MEXT)
- Ritsumeikan Global Innovation Research Organization (R-GIRO)
- New Energy and the Industrial Technology Development Organization (NEDO) of Japan
- Grants-in-Aid for Scientific Research [21249002] Funding Source: KAKEN
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The excellent oxidizing behavior of the mu-oxo-bridged phenyliodine trifluoroacetate 1 is revealed during the phenolic oxidations mediated by hypervalent iodine(III) reagents. The use of the mu-oxo-bridged compound 1 instead of PhI(OAc)(2) (PIDA) and PhI(OCOCF3)(2) (PIFA) during the oxidative cyclization of phenols involving carbon-oxygen, carbon-nitrogen, and carbon-carbon bond formations could produce spirocyclized cyclohexadienones in comparable or somewhat better yields. Thus, we have concluded that the unique reagent 1 is a promising alternative to PIDA and PIFA, and the use of reagent 1 as a reasonable choice is recommended for the hypervalent iodine(III)-mediated phenolic oxidations as well as other transformations. (C) 2010 Elsevier Ltd. All rights reserved.
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