Thiol on silica as a ‘catch and release’ support for isocyanates to afford ureas

Silica-bound thiocarbamates were prepared by Curtius rearrangement of carboxylic acids in the presence of thiol on silica gel. The solid supported thiocarbamates were found to be stable isocyanate equivalents, which upon treatment with amines efficiently afforded di- and tri-substituted ureas. The u...

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Bibliographic Details
Published in:Tetrahedron letters 2007-07, Vol.48 (28), p.4925-4927
Main Authors: Bolshan, Yuri, Tomaszewski, Miroslaw J., Santhakumar, Vijayaratnam
Format: Article
Language:English
Subjects:
Catch and release
Curtius rearrangement
Solid phase synthesis
Thiocarbamate
Urea
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Summary:Silica-bound thiocarbamates were prepared by Curtius rearrangement of carboxylic acids in the presence of thiol on silica gel. The solid supported thiocarbamates were found to be stable isocyanate equivalents, which upon treatment with amines efficiently afforded di- and tri-substituted ureas. The urea products released from the catch and release support were, in the majority of cases, greater than 95% pure and required no further work up.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2007.05.050