Oxidation of Tertiary Amines to NOxides

Previous reviews have dealt with metal-catalyzed [76] and stoichiometric [77] oxidation of amines in a broad sense. This section will be limited to the selective oxidation of tertiary amines to N-oxides. Amine N-oxides are synthetically useful compounds [78, 79] and are frequently used stoichiometric oxidants in osmium- [81-82] manganese- [83] and ruthenium-catalyzed [84, 85] oxidations, as well as in other organic transformations [86-88]. Aliphatic tert-amine N-oxides are useful surfactants [79] and are essential components in hair conditioners, shampoos, toothpaste, cosmetics, etc. [89].

Because of their importance, various methods have been reported for the oxidation of tertiary amines to N-oxides. The oxidations of amines will be divided into the following sections: (1) stoichiometric reactions, (2) chemocatalytic reactions, and (3) biocatalytic reactions. Finally we provide some examples where N-oxides are generated in situ as catalytic oxotransfer species in catalytic transformations.

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