Catalytic Oxidation of Silyl Enol Ethers to 1,2-Diketones Employing Nitroxyl Radicals

Masaki Hayashi, Masatoshi Shibuya, Yoshiharu Iwabuchi*

*Department of Organic Chemistry, Graduate School of Pharmaceutical Sciences, Tohoku University, 6-3 Aobayama, Sendai 980-8578, Japan, Email: iwabuchimail.pharm.tohoku.ac.jp

M. Hayashi, M. Shibuya, Y. Iwabuchi, Synlett, 2012, 23, 1025-1030.

DOI: 10.1055/s-0031-1290528

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Abstract

A series of α-diketones were readily prepared by the nitroxyl-radical-catalyzed oxidation of silyl enol ethers using magnesium monoperoxyphthalate hexahydrate (MMPP • 6 H₂O) as the co-oxidant.

see article for more examples

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Oxidation of Alcohols to Carbonyl Compounds with Diisopropyl Azodicarboxylate Catalyzed by Nitroxyl Radicals

M. Hayashi, M. Shibuay, Y. Iwabuchi, J. Org. Chem., 2012, 77, 3005-3009.

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Key Words

oxidation, catalysis, enols, diketones, nitroxyl radical, Nor-Azado, MMPP • 6 H₂O

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ID: J60-Y2012-1080