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Article
Bulk Gold-Catalyzed Reactions of Isocyanides, Amines, and Amine N-Oxides
Organometallics
  • Erik R. Klobukowski, Iowa State University
  • Robert J. Angelici, Iowa State University
  • L. Keith Woo, Iowa State University
Document Type
Article
Disciplines
Publication Version
Published Version
Publication Date
1-1-2012
DOI
10.1021/om201068g
Abstract
Bulk 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.
Comments

Reprinted (adapted) with permission from Organometallics 31 (2012): 2785, doi:10.1021/om201068g. Copyright 2012 American Chemical Society.

Copyright Owner
American Chemical Society
Language
en
File Format
application/pdf
Citation Information
Erik 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/