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Yamada Coupling

Published Online: 15 SEP 2010

DOI: 10.1002/9780470638859.conrr687

Comprehensive Organic Name Reactions and Reagents

Comprehensive Organic Name Reactions and Reagents

How to Cite

2010. Yamada Coupling. Comprehensive Organic Name Reactions and Reagents. 687:3105–3108.

Publication History

  1. Published Online: 15 SEP 2010

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Abstract

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.

Keywords:

  • dicyclohexylcarbodiimide;
  • diethylphosphoryl cyanide;
  • diphenylphosphoryl azide;
  • triethylamine