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

Eric A. Skrotzki, Jaya Kishore Vandavasi and Stephen G. Newman*

*Department of Chemistry & Biomolecular Sciences, 10 Marie Curie, University of Ottawa, Ottawa, Ontario, Canada, K1N 6N5, Email:

E. A. Skrotzki, J. K. Vandavasi, S. G. Newman, J. Org. Chem., 2021, 86, 14169-14176.

DOI: 10.1021/acs.joc.1c00768

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The high reactivity of ozone and its propensity to overoxidize organic molecules, including most solvents can largely be mitigated by adsorbing both substrate and ozone onto silica gel, providing a solvent-free oxidation method. A flow-based packed bed reactor approach provides exceptional control of temperature and time for oxidation of amines to nitroalkanes and the synthesis of pyridine N-oxides.

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Key Words

nitro compounds, ozone

ID: J42-Y2021