Over the past decade, there has been an increased interest in the use of TEMPO-based oxidants and their oxoammonium salt counterparts due in part to their “greenness” and remarkable selectivity. A number of these oxidants are commercially available and can also be prepared in high yields on multi-mole scale in a few short steps. These nitroxide-based oxidants have been extensively used both stoichiometrically and catalytically (either through electrochemical generation or by use of a secondary oxidant) for oxidations of alcohols to their corresponding carbonyl compounds. More recently, methods to selectively convert amines to imines and nitriles, as well as thiols to disulfides have been developed and will be discussed. The user’s choice of solvent, bases, additives, stoichiometry, and secondary oxidants have been shown to influence the selectivity of these oxidants and the overall course of the reactions. The navigation of reaction conditions to furnish the desired products will be discussed.

How conditions influence the reactivity and selectivity of oxoammonium salt-based oxidants

ACS Spring 2022

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