Chemistry (Weinheim an der Bergstrasse, Germany) · 2009
Efficient oxidation of 1,2-diols into alpha-hydroxyketones catalyzed by organotin compounds.
СтатьяПоддержка исследования: вне правительства СШАНазвание и аннотация: Перевод в очереди
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Maki Toshihide, Iikawa Shinya, Mogami Gen, Harasawa Hitomi, Matsumura Yoshihiro, Onomura Osamu
Аннотация
Electrochemical oxidation of 1,2-diols with a catalytic amount of an organotin compound and a bromide ion as mediators has been developed. Various cyclic and acyclic 1,2-diols were oxidized into the corresponding alpha-hydroxyketones in good to excellent yields without C-C bond cleavage. Also, oxidation with the use of chemical oxidants was accomplished in the presence of a catalytic amount of an organotin compound. These reactions could discriminate 1,2-diols from isolated hydoxyl groups or 1,3-diols. In the case of a conformationally restricted cyclic 1,2-diol, the axial hydroxyl group was oxidized exclusively. Mono-, di-, and trialkylated tin compounds were examined as mediators and dialkylated tin compounds showed higher catalytic activity than mono- and trisubstituted ones. Me(2)SnCl(2) was found to be the most suitable mediator for the selective oxidation.