4.6 Article

2,2,2-Trifluoroacetophenone as an Organocatalyst for the Oxidation of Tertiary Amines and Azines to N-Oxides

Journal

CHEMISTRY-A EUROPEAN JOURNAL
Volume 20, Issue 2, Pages 559-563

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201303360

Keywords

green chemistry; hydrogen peroxide; N-oxides; organocatalysis; oxidation

Funding

  1. Operational Program Education and Lifelong Learning through the NSRF program ENISigmaXYSigmaH METADeltaIDeltaAK TOOOmegaN EREYNHTOmegaN [PE 2431]
  2. ESF
  3. Greek State

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A cheap, mild and environmentally friendly oxidation of tertiary amines and azines to the corresponding N-oxides is reported by using polyfluoroalkyl ketones as efficient organocatalysts. 2,2,2-Trifluoroacetophenone was identified as the optimum catalyst for the oxidation of aliphatic tertiary amines and azines. This oxidation is chemoselective and proceeds in high-to-quantitative yields utilizing 10 mol% of the catalyst and H2O2 as the oxidant.

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