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).

http://www.chtf.stuba.sk/~szolcsanyi/education/files/Organicka%20chemia%20II/Prednaska%208_Aminokyseliny%20a%20peptidy/Doplnkove%20studijne%20materialy/Amide%20bond%20formation/Amide%20bond%20formation%20-%20beyond%20the%20myth%20of%20coupling%20reagents.pdf

Amide bond formation: beyond the myth of coupling reagents

Chem. Pharm. Bull.(オピニオン)

Artificial photosynthesis: molecular systems for catalytic water oxidation.

Peptide Coupling Reagents, More than a Letter Soup Ayman El-Faham* and Fernando Albericio* Institute for Research in Biomedicine, Barcelona Science Park, Baldiri Reixac 10, 08028-Barcelona, Spain Alexandria University, Faculty of Science, Department of Chemistry, P.O. Box 426, Ibrahimia, 21321 Alexandria, Egypt CIBER-BBN, Networking Centre on Bioengineering, Biomaterials and Nanomedicine, Barcelona Science Park, Baldiri Reixac 10, 08028-Barcelona, Spain. Department of Organic Chemistry, University of Barcelona, Martí i Franqu es 1-11, 08028-Barcelona, Spain

Peptide coupling reagents, more than a letter soup

Amongst the many ways of constructing the amide bond, there has been a growing interest in the use of metal-catalysed methods for preparing this important functional group. In this tutorial review, highlights of the recent literature have been presented covering the key areas where metal catalysts have been used in amide bond formation. Acids and esters have been used in coupling reactions with amines, but aldehydes and alcohols have also been used in oxidative couplings. The use of nitriles and oximes as starting materials for amide formation are also emerging areas of interest. The use of carbon monoxide in the transition metal catalysed coupling of amines has led to a powerful methodology for amide bond formation and this is complemented by the addition of an aryl or alkenyl group to an amide typically using palladium or copper catalysts.

http://www.chtf.stuba.sk/~szolcsanyi/education/files/Organicka%20chemia%20II/Prednaska%208_Aminokyseliny%20a%20peptidy/Doplnkove%20studijne%20materialy/Amide%20bond%20formation/Metal-catalysed%20approaches%20to%20amide%20bond%20formation.pdf

Metal-catalysed approaches to amide bond formation

Amide Bond Formation: Beyond the Myth of Coupling Reagents

PS-IIDQ: a supported coupling reagent for efficient and general amide bond formation

PS-IIDQ: an efficient polymer-supported amide coupling reagent

Polystyrene-IIDQ is a polymer-supported coupling reagent that couples carboxylic acids to amines in good yields and high purity without the requirement of a pre-activation step. Importantly the order of addition of the amine, acid or coupling agent makes no difference to the efficiency of the coupling reaction and the reagent can be readily regenerated.

Eric Valeur

Papers

Amide bond formation: beyond the myth of coupling reagents

Amide Bond Formation: Beyond the Myth of Coupling Reagents

PS-IIDQ: a supported coupling reagent for efficient and general amide bond formation

PS-IIDQ: an efficient polymer-supported amide coupling reagent

PS‐IIDQ: An Efficient Polymer‐Supported Amide Coupling Reagent.