5-Nitroso-1,3-diphenyltetrazolium salt as a mediator for the oxidation of alcohols

Matsukawa, Yuta; Hirashita, Tsunehisa; Araki, Shuki

5-Nitroso-1,3-diphenyltetrazolium salt as a mediator for the oxidation of alcohols

2017

Matsukawa, Yuta | Hirashita, Tsunehisa | Araki, Shuki

We describe the synthesis of a mesoion-derived nitroso compound, 5-nitroso-1,3-diphenyltetrazolium tetrafluoroborate (1), and its application in the oxidation of alcohols. The structure of 1 was fully characterized by X-ray analysis, showing that it exists as a monomer in the solid state. In the cyclic voltammetric analysis of 1, a reversible redox peak was observed at 0.43 V (vs. Ag/Ag+ in MeCN) under acidic conditions. It was subsequently shown that the nitrosotetrazolium salt 1 is capable of stoichiometrically oxidizing alcohols to the corresponding carbonyl compounds effectively. This nitroso heterocycle and its reduced form, i.e., the corresponding mesoionic hydroxyamide, participate in a redox cycle involving the catalytic oxidation of alcohols by the aid of HNO3 under mild conditions.

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