Organic iodine(V) compounds as terminal oxidants in iron(III) phthalocyanine catalyzed oxidation of alcohols

Ivan M. Geraskin, Matthew W. Luedtke, Heather M. Neu, Victor N. Nemykin, Viktor Zhdankin

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Abstract

The pseudocyclic iodine(V) oxidants, such as esters of iodoxybenzoic acid (IBX-esters) and 2-iodylphenol ethers, can serve as stable and efficient sources of oxygen in catalytic oxidations, and their reactivity is similar to the commonly used thermally unstable and potentially explosive iodosylbenzene. In a specific example, primary or secondary benzylic alcohols are selectively oxidized by isopropyl IBX-ester in the presence of μ-oxo-(tetra-tert-butylphthalocyaninato)iron(III) (0.1 mol equiv) in dichloromethane at room temperature in 0.5-2 h to afford the respective carbonyl compounds in 100% conversion and preparative yields 91-95% after column chromatography.

Original languageEnglish (US)
Pages (from-to)7410-7412
Number of pages3
JournalTetrahedron Letters
Volume49
Issue number52
DOIs
StatePublished - Dec 22 2008

Bibliographical note

Funding Information:
This work was supported by a research Grant from the National Science Foundation (Grant CHE-0702734) and Petroleum Research Fund, administered by the American Chemical Society (Grant PRF-45510-GB-3).

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