Ozone-Mediated Amine Oxidation and Beyond: A Solvent Free, Flow-Chemistry Approach

Eric A. Skrotzki^a, Jaya Kishore Vandavasi^a, Stephen G. Newman^a

• ^aCentre for Catalysis Research and Innovation, Department of Chemistry and Biomolecular Sciences, University of Ottawa, 10 Marie-Curie, Ottawa, Ontario K1N 6N5, Canada.

Ozone is a powerful oxidant, most commonly used for oxidation of alkenes to carbonyls. The synthetic utility of other ozone-mediated reactions is hindered by its high reactivity and propensity to over-oxidize organic molecules, including most solvents. This challenge can largely be mitigated by adsorbing both substrate and ozone onto silica gel, providing a solvent-free oxidation method. In this manuscript, a flow-based packed bed reactor approach is described that provides exceptional control of reaction temperature and time of this reaction to achieve improved control and chemoselectivity over this challenging reaction. A powerful method to oxidize primary amines into nitroalkanes is achieved. Examples of pyridine, C–H bond, and arene oxidations are also demonstrated, confirming the system is generalizable to diverse ozone-mediated processes.

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