Synthesis of Urea Derivatives from CO 2 and Silylamines

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 CO 2 . This protocol is shown to provide facile access to 13 C‐labeled ureas, as well as chiral and macrocyclic ureas. These reactions proceed through init...

Full description

Saved in:
Bibliographic Details
Published in:Angewandte Chemie International Edition 2019-04, Vol.58 (17), p.5707-5711
Main Authors: Xu, Maotong, Jupp, Andrew R., Ong, Maegan S. E., Burton, Katherine I., Chitnis, Saurabh S., Stephan, Douglas W.
Format: Article
Language:English
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary: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 CO 2 . 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.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201900058