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Ozone-Mediated Amine Oxidation and Beyond: A Solvent Free, Flow-Chemistry Approach
preprintsubmitted on 01.03.2021, 16:14 and posted on 02.03.2021, 11:28 by Eric Skrotzki, Jaya Kishore Vandavasi, Stephen Newman
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.
Natural Sciences and Engineering Research Council of Canada (NSERC)
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