Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 58, Issue 17, Pages 5707-5711Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201900058
Keywords
carbon dioxide; macrocyclic ureas; silylamines; silyl carbamates; urea
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Funding
- NSERC of Canada
- Qatar Foundation Research Foundation [NPRP8-235-1-055]
- Canada Research Chair
- Visiting Einstein Fellowship at TU Berlin
- Banting Postdoctoral Fellowship
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A series of thirty-three N, N'-diaryl, dialkyl, and alkyl-aryl ureas have been prepared in pyridine or toluene by reaction of silylamines with CO2. This protocol is shown to provide facile access to C-13-labeled ureas, as well as chiral and macrocyclic ureas. These reactions proceed through initial generation of the corresponding silylcarbamates, which subsequently react with silylamine under thermal conditions to afford the thermodynamically favored urea and disilyl ether.
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