Oxidative Syntheses of N,N‑Dialkylhydroxylamines

Despite the wide utility of hydroxylamines in organic synthesis, relatively few are commercially available, and there is a need for direct, efficient, and selective methods for their synthesis. Herein, we report two complementary methods to accomplish direct oxidation of secondary amines using UHP a...

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Published inJournal of organic chemistry Vol. 89; no. 12; pp. 8767 - 8772
Main Authors Barriault, Daniel, Ly, Huy M., Allen, Meredith A., Gill, Monica A., Beauchemin, André M.
Format Journal Article
LanguageEnglish
Published United States American Chemical Society 21.06.2024
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Summary:Despite the wide utility of hydroxylamines in organic synthesis, relatively few are commercially available, and there is a need for direct, efficient, and selective methods for their synthesis. Herein, we report two complementary methods to accomplish direct oxidation of secondary amines using UHP as an oxidant. The first method uses 2,2,2-trifluoroethanol (TFE) and a large excess of amine. Isolation of hydroxylamine products is enabled by selective salt formation, and recovery of excess amine is demonstrated. The second method uses hexafluoroacetone as an additive and is highlighted by the 1:1 stoichiometry between the oxidant and amine.
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ISSN:0022-3263
1520-6904
1520-6904
DOI:10.1021/acs.joc.4c00674