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Synfacts 2025; 21(10): 1052
DOI: 10.1055/a-2680-9601
Innovative Drug Discovery and Development

An Organic Catalyst for Room-Temperature Amidation

Authors

    Contributor(s):

  • Dirk Trauner

  • Robert Gaston Jr.

Reid KAW, Sutio R, Ranani JM, Pavlenko M, Slaney BE, Allais C, Lee JW *, Sandford C *. Pfizer Chemical Research and Development, Groton, and University of Texas at San Antonio, USA
A Bifunctional Boronic Acid/Phosphorus(V) Organocatalyst for the Direct Room-Temperature Amidation of Carboxylic Acids.

Chem Catal. 2025;
5: 101460
DOI: 10.1016/j.checat.2025.101460
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Keywords

organocatalysis - bifunctional catalyst - oxyphosphonium intermediate - amidation

Significance

The authors report a boronic acid/phosphorus(V) catalyst that promotes amide bond formation under mild conditions. Amide bonds are ubiquitous in pharmaceutical drugs and biology making them an important target for methodological development. Another useful aspect of this work is the mild and relatively green conditions used to make various amide bonds with an organic catalyst.


 

Comment

Treating a carboxylic acid and an amine with organocatalyst A in the presence of molecular sieves promotes amide bond formation at room temperature. Mechanistic investigations support an oxyphosphonium intermediate that is intercepted by the carboxylic acid and then attacked by the amine. The scope includes various amines and carboxylic acids without losing enantiomeric excess. Electron-deficient or sterically hindered acids as well as anilines were incompatible substrates.


 

 

Publication History

Article published online:
23 September 2025

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