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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 (free Supporting Information)


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.


Key Words

organocatalysis, aerobic oxidation, sulfides, sulfoxides, flavin catalyst


ID: J60-Y2013