Reinvestigation of the Organocatalyzed Aerobic Oxidation of Aldehydes to Acids

Laurent Vanoye (1) , Mohamed Abdelaal (1) , Kacy Grundhauser (1) , Boris Guicheret (1) , Pascal Fongarland (1) , Claude de Bellefon (1) , Alain Favre-Réguillon (2, 1, 3)

1 LGPC - Laboratoire de Génie des Procédés Catalytiques
2 CNAM - Conservatoire National des Arts et Métiers [CNAM]
3 LTCP - Laboratoire de transformations chimiques et pharmaceutiques

The organocatalyzed aerobic oxidation of aldehydes to acids was reproduced from the original report. In- and ex-situ analysis of the reaction mixture as the function of time reveals that, unlike the claim in the publication, the aerobic oxidation of aromatic and aliphatic aldehydes leads predominantly to the formation of peracids. The latter are transformed into the corresponding carboxylic acids during the workup procedure. The buildup of peracids in solution poses safety problems that should not be overlooked. This finding has also an influence on the way new catalysts are investigated to improve this reaction as well as on aerobic aldehyde-mediated co-oxidation.

Domaines: Chimie

Laurent Vanoye, Mohamed Abdelaal, Kacy Grundhauser, Boris Guicheret, Pascal Fongarland, et al.. Reinvestigation of the Organocatalyzed Aerobic Oxidation of Aldehydes to Acids. Organic Letters, 2019, 21 (24), pp.10134-10138. ⟨10.1021/acs.orglett.9b04193⟩. ⟨hal-04047083⟩