Bulk Gold-Catalyzed Reactions of Isocyanides, Amines, and Amine N-Oxides
| Title | Bulk Gold-Catalyzed Reactions of Isocyanides, Amines, and Amine N-Oxides |
| Publication Type | Journal Article |
| Year of Publication | 2012 |
| Authors | Klobukowski ER, Angelici RJ, Woo LK |
| Journal Title | Organometallics |
| Volume | 31 |
| Pages | 2785-2792 |
| Date Published | 04 |
| Type of Article | Article |
| ISBN Number | 0276-7333 |
| Accession Number | WOS:000303076600034 |
| Keywords | aerobic oxidation, chemistry, complexes, ligands, metal-carbonyls, non-nanogold catalysis, oxygen, POLYMERIZATION, secondary-amines, surfaces |
| Abstract | Bulk gold powder (similar to 5-50 mu m particles) catalyzes the reactions of isocyanides with amines and amine N-oxides to produce ureas. The reaction of n-butyl isocyanide (Bu-n-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((NHBu)-Bu-n)((NPr2)-Pr-n)) in 99% yield at 60 degrees 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. |
| URL | <Go to ISI>://WOS:000303076600034 |
| DOI | 10.1021/om201068g |
| Alternate Journal | Organometallics |
