Published Online: 15 SEP 2010
Copyright © 2010 John Wiley & Sons, Inc. All rights reserved.
Comprehensive Organic Name Reactions and Reagents
How to Cite
2010. Yamada Coupling. Comprehensive Organic Name Reactions and Reagents. 687:3105–3108.
- Published Online: 15 SEP 2010
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The condensation reaction between a carboxylic acid and an amine to form an amide with diethylphosphoryl cyanide (DEPC) as the coupling reagent, is referred to as the Yamada coupling. This reaction has shown some advantages over other peptide condensation reagents, including dicyclohexylcarbodiimide (DCC) and diphenylphosphoryl azide (DPPA). However, by use of diphenylphosphoryl azide as the coupling reagent, significant amount of side products due to the Curtius rearrangement have been observed. Several other coupling reagents, such as DMF, dichloromethane (DCM) have also been compared. Moreover, the coupling result using DEPC has been reported inferior to TBTU. This reaction is very useful for the preparation of peptides without racemization of amino acids.
- diethylphosphoryl cyanide;
- diphenylphosphoryl azide;