Synthesis of Urea Derivatives from CO2 and Silylamines. Issue 17 (20th March 2019)

• Record Type: Journal Article
• Authors: Xu, Maotong; Jupp, Andrew R.; Ong, Maegan S. E.; Burton, Katherine I.; Chitnis, Saurabh S.; Stephan, Douglas W.
• Is Part Of: Angewandte Chemie international edition. Volume 58:Issue 17(2019)
• Page Start: 5707
• Page End: 5711
• Publication Date: 2019-03-20
• Subjects: carbon dioxide -- macrocyclic ureas -- silylamines -- silyl carbamates -- urea; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201900058
• Languages: English
• ISSNs: 1433-7851

Abstract

Abstract: 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 13 C‐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. Abstract : Urea‐lly got me : Silylamines react with CO2 to give facile access to silylcarbamates or the corresponding aryl or alkyl ureas. This procedure also provides a convenient route to 13 C‐labelled, chiral or macrocyclic derivatives.