Organic iodine(V) compounds as terminal oxidants in iron(III) phthalocyanine catalyzed oxidation of alcohols |
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Authors: | Ivan M Geraskin Viktor V Zhdankin |
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Institution: | Department of Chemistry and Biochemistry, University of Minnesota Duluth, Duluth, MN 55812, USA |
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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. |
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