Insights into the oxidative dehydrogenation of amines with nanoparticulate iridium oxide

Hammond, Ceri ORCID: https://orcid.org/0000-0002-9168-7674, Schuemperli, Martin T. and Hermans, Ive 2013. Insights into the oxidative dehydrogenation of amines with nanoparticulate iridium oxide. Chemistry - a European Journal 19 (39) , pp. 13193-13198. 10.1002/chem.201301596

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Abstract

The aerobic oxidation of amines offers a promising route towards many versatile chemical compounds. Within this contribution, we extend our previous investigations of iridium oxide-catalyzed alcohol oxidation to amine substrates. In addition to demonstrating the versatility of this catalyst, particular attention is focused on the mechanisms of the reaction. Herein, we demonstrate that although amines are oxidized slower than the corresponding alcohols, the catalyst has a preference for amine substrates, and oxidizes various amines at turnover frequencies greater than other systems found in the open literature. Furthermore, the competition between double amine dehydrogenation, to yield the corresponding nitrile, and amine-imine coupling, to yield the corresponding coupled imine, has been found to arise from a competitive reaction pathway, and stems from an effect of substrate-to-metal ratio. Finally, the mechanism responsible for the formation of N-benzylidene-1-phenylmethanamine was examined, and attributed to the coupling of free benzyl amine substrate and benzaldehyde, formed in situ through hydrolysis of the primary reaction product, benzyl imine.

Item Type:	Article
Date Type:	Publication
Status:	Published
Schools:	Chemistry
Subjects:	Q Science > QD Chemistry
Uncontrolled Keywords:	amines; heterogeneous catalysis; kinetics; oxidation; reaction mechanisms
Publisher:	Wiley Blackwell
ISSN:	0947-6539
Last Modified:	25 Oct 2022 09:10
URI:	https://orca.cardiff.ac.uk/id/eprint/57519

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