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

J Org Chem. 2021 Oct 1;86(19):13817-13823. doi: 10.1021/acs.joc.1c01888. Epub 2021 Sep 16.

Abstract

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.