Bulk Gold-Catalyzed Reactions of Isocyanides, Amines, and Amine N-OxidesOrganometallics
Publication VersionPublished Version
AbstractBulk gold powder (∼5–50 μm particles) catalyzes the reactions of isocyanides with amines and amine N-oxides to produce ureas. The reaction of n-butyl isocyanide (nBu–N≡C) with di-n-propylamine and N-methylmorpholine N-oxide in acetonitrile, which was studied in the greatest detail, produced 3-butyl-1,1-dipropylurea (O═C(NHnBu)(NnPr2)) in 99% yield at 60 °C within 2 h. Sterically and electronically different isocyanides, amines, and amine N-oxides react successfully under these conditions. Detailed studies support a two-step mechanism that involves a gold-catalyzed reaction of adsorbed isocyanide with the amine N-oxide to form an isocyanate (RN═C═O), which rapidly reacts with the amine to give the urea product. These investigations show that bulk gold, despite its reputation for poor catalytic activity, is capable of catalyzing these reactions.
Copyright OwnerAmerican Chemical Society
Citation InformationErik R. Klobukowski, Robert J. Angelici and L. Keith Woo. "Bulk Gold-Catalyzed Reactions of Isocyanides, Amines, and Amine N-Oxides" Organometallics Vol. 31 Iss. 7 (2012) p. 2785 - 2792
Available at: http://works.bepress.com/l-woo/26/