4.7 Article

Metal-Free Solvent Promoted Oxidation of Benzylic Secondary Amines to Nitrones with H2O2

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 86, Issue 19, Pages 13817-13823

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.1c01888

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Funding

  1. FEDER/Ministerio de Ciencia, Innovacion y Universidades-Agencia Estatal de Investigacion [PGC2018-098660-B-I00]
  2. CAPES [001]
  3. CNPq [310514/2018-5]
  4. FAPEMIG

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An environmentally friendly protocol for the generation of C-aryl nitrones from benzylic secondary amines using catalyst-free oxidation with H2O2 in MeOH or CH3CN is described. This method provides a selective access to a variety of C-aryl nitrones with yields ranging from 60% to 93%. Several studies have been conducted to elucidate the reaction mechanism and the role of the solvent.
An environmentally benign protocol for the generation of nitrones from benzylic secondary amines via catalyst-free oxidation of secondary amines using H2O2 in MeOH or CH3CN is described. This methodology provides a selective access to a variety of C-aryl nitrones in yields of 60 to 93%. Several studies have been performed to shed light on the reaction mechanism and the role of the solvent.

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