Scientific Results

Gold Supported on Silica Catalyzes the Aerobic Oxidation of N,N-Disubstituted Hydroxylamines to Nitrones

Year: 2015

Authors: D’Adamio G., Parmeggiani C., Goti A., Cardona F.

Autors Affiliation: Dipartimento di Chimica “Ugo Schiff”, University of Florence, Sesto Fiorentino Italy;
Istituto Nazionale di Ottica at LENS, Consiglio Nazionale delle Ricerche, Sesto Fiorentino Italy

Abstract: A new method for the preparation of nitrones through the aerobic oxidation of the corresponding N,N-disubstituted hydroxylamines has been developed by exploring a new catalytic reactivity of gold supported on silica. The oxidation occurs under very mild conditions (flux of air, methanol or water, room temperature). The oxidation of a range of highly functionalized hydroxylamines with complete conversions and excellent yields of nitrones illustrates the selectivity, efficiency, and reliability of this practical method. The oxidation was shown to take place chemoselectively in competition experiments with benzyl alcohol and dibutylamine.

Journal/Review: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY

Volume: 2015 (29)      Pages from: 6541  to: 6546

More Information: We thank the Ministero dell\’Universita e della Ricerca (MIUR), Italy (PRIN 2010-2011, 2010L9SH3K 006) and the Ministero della Salute, Regione Toscana (Ricerca Finalizzata, RF-2011-02347694) for financial support. We thank Dr. Annalisa Guerri and Dr. Laura Chelazzi for XRPD measurements.
KeyWords: Nitrones; Hydroxylamines; Gold; Nanoparticles; Oxidation
DOI: 10.1002/ejoc.201501001

Citations: 10
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English