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Tetrahedron Letters
Volume 40, Issue 14, 2 April 1999, Pages 2669-2672
 
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doi:10.1016/S0040-4039(99)00302-0    
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Copyright © 1999 Published by Elsevier Science Ltd.

A new protocol for the formation of carbamates and thiocarbamates using carbamoyl imidazolium salts

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Robert A. Batey*a, Chiaki Yoshina-Ishiia, Scott D. Taylorb and V. Santhakumara

a Department of Chemistry, Lash Miller Laboratories, 80 St. George Street, University of Toronto, Toronto, Ontario, M5S 3H6, Canada

b Department of Chemistry, University of Toronto at Mississauga, 3359 Mississauga Rd. N., Mississauga, Ontario, L5L 1C6, Canada


Received 5 November 1998; 
accepted 1 February 1999. ;
Available online 21 May 1999.

Abstract

Carbamoyl imidazolium salts are demonstrated to act as useful carbamoylation reagents, in reactions with alcohols, phenols, thiols and thiophenols to form carbamates and thiocarbamates under relatively mild conditions. The salts are stable and easily prepared from the corresponding amines using CDI.

Graphical Abstract

Carbamoyl imidazolium salts are shown to be useful carbamoyl cation equivalents. Thus, reaction of these salts with phenols, alcohols or thiols results in the formation of carbamates and thiocarbamates in high yields under mild conditions.


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Tetrahedron Letters
Volume 40, Issue 14, 2 April 1999, Pages 2669-2672
 
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