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Anaerobic Nitroxide-Catalyzed Oxidation of Alcohols Using the NO+/NO· Redox Pair

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journal contribution
posted on 03.01.2014, 00:00 by Martin Holan, Ullrich Jahn
A new method for alcohol oxidation using TEMPO or AZADO in conjunction with BF3·OEt2 or LiBF4 as precatalysts and tert-butyl nitrite as a stoichiometric oxidant has been developed. The system is based on a NO+/NO· pair for nitroxide reoxidation under anaerobic conditions. This allows the simple, high-yielding conversion of various achiral and chiral alcohols to carbonyl compounds without epimerization and no formation of nonvolatile byproducts.