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

Masaki Hayashi, Masatoshi Shibuya and 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. Shibuay, Y. Iwabuchi, J. Org. Chem., 2012, 77, 3005-3009.

DOI: 10.1021/jo202588j (free Supporting Information)


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Abstract

A nitroxyl-radical-catalyzed oxidation using diisopropyl azodicarboxylate (DIAD) allows the conversion of various primary and secondary alcohols to their corresponding aldehydes and ketones without overoxidation to carboxylic acids. 1,2-Diols are oxidized to hydroxyl ketones or diketones depending on the amount of DIAD used.


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

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


Key Words

Aldehydes, Ketones, DIAD, Nor-AZADO, Organocatalysis


ID: J42-Y2012-0860