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Updated: Jun 24, 2026

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Published on: June 20, 2014
Diphenyldiselenide-catalyzed selective oxidation of activated alcohols with tert-butyl hydroperoxide: new mechanistic
John C van der Toorn1, Gerjan Kemperman, Roger A Sheldon
1Laboratory for Biocatalysis and Organic Chemistry, Delft University of Technology, Julianalaan 136, 2628 BL Delft, The Netherlands.
Abstract:
Diselenides are known precatalysts for catalytic oxidations. The use of these widely available compounds as catalysts for the oxidation of alcohols was investigated, still leaving many mechanistic questions to be answered. By using a range of analytical techniques, we found evidence for the unexpected involvement of seleninic anhydride in the catalytic mechanism. The activation time of the diselenide and its influence on the oxidation reaction itself was also investigated. On the basis of these findings, an improved protocol for the selective oxidation of activated alcohols was devised resulting in significantly decreased catalyst loadings (<1%).
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