Amide bond formation: beyond the myth of coupling reagents.

@article{Valeur2009AmideBF,
  title={Amide bond formation: beyond the myth of coupling reagents.},
  author={Eric Valeur and Mark Bradley},
  journal={Chemical Society reviews},
  year={2009},
  volume={38 2},
  pages={
          606-31
        }
}
Amide bond formation is a fundamentally important reaction in organic synthesis, and is typically mediated by one of a myriad of so-called coupling reagents. This critical review is focussed on the most recently developed coupling reagents with particular attention paid to the pros and cons of the plethora of "acronym" based reagents. It aims to demystify the process allowing the chemist to make a sensible and educated choice when carrying out an amide coupling reaction (179 references). 
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References

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Abstract The potential application of 1-oxo-1-chlorophospholane (5) as a novel reagent for the in situ activation of Nα -protected amino acids for use in peptide bond forming reactions has been… Expand
The myth of coupling reagents.
Coupling reagents have been proposed for peptide synthesis ever since the introduction of the method because of the convenience of the procedure, which consists of peptide bond formation by addition… Expand
A low-epimerizing peptide coupling reagent based on the rearrangement of a carboxylic-sulfonic mixed anhydride
Abstract A series of peptides has been prepared using an o -hydroxybenzenesulfonyl chloride as the condensation reagent. Experimentally, the coupling is a one pot two-steps reaction: formation and… Expand
Design and Synthesis of New Immonium‐Type Coupling Reagents
A new family of immonium-type coupling reagents is described here. The differences in the carbocation skeletons of these reagents can be correlated with differences in stability and thus reactivity.… Expand
(Chloro-phenylthio-methylene)dimethylammonium chloride (CPMA): a new coupling reagent for the formation of ester and amide bond
CPMA is an efficient agent for the formation of esters and amides from carboxylic acids. It is compatible with substrates that are sensitive to basic conditions or oxophilic reagents. The reaction… Expand
PS-IIDQ: a supported coupling reagent for efficient and general amide bond formation
Polystyrene-IIDQ, a polymer-supported coupling reagent, was synthesized in three steps from Merrifield resin in 86% overall conversion. This reagent efficiently coupled carboxylic acids to amines in… Expand
Polymer-supported Mukaiyama reagent: a useful coupling reagent for the synthesis of esters and amides.
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TLDR
A reaction in which primary amines are directly acylated by equimolar amounts of alcohols to produce amides and molecular hydrogen in high yields and high turnover numbers is reported. Expand
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