Aerobic Oxidation of Sulfides with a Vitamin B₂-Derived Organocatalyst

Yasushi Imada*, Itoko Tonomura, Naruyoshi Komiya, Takeshi Naota*

*Department of Chemistry, Graduate School of Engineering Science, Osaka University, Machikaneyama 1-3, Toyonaka, Osaka 560-8531, Japan, Email: imadachem.tokushima-u.ac.jp, naotachem.es.osaka-u.ac.jp

Y. Imada, I. Tonomura, N. Komiya, T. Naota, Synlett, 2013, 24, 1679-1682.

DOI: 10.1055/s-0033-1339276

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Abstract

5-Ethyl-3-methyl-2′,4′:3′,5′-di-O-methylenedioxy-riboflavinium perchlorate, which is readily derived from commercially available vitamin B₂, exhibits high catalytic activity for the oxidation of organic sulfides under an oxygen atmosphere with the assistance of hydrazine hydrate as a reductant. This is an inexpensive, convenient, and environmentally benign method for the selective oxidative transformation of sulfides into sulfoxides.

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Flavin Catalyzed Oxidations of Sulfides and Amines with Molecular Oxygen

Y. Imada, H. Iida, S. Ono, S.-I. Murahashi, J. Am. Chem. Soc., 2003, 125, 2868-2869.

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Key Words

organocatalysis, aerobic oxidation, sulfides, sulfoxides, flavin catalyst

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ID: J60-Y2013