A Strategy for Improving the Efficiency of Boronic Acid Catalysis in the Synthesis of Amides

This study outlines the development of novel boronic acids as catalysts for the direct synthesis of amides from carboxylic acids and amines. The Lewis acidity of the boronic acids was estimated by means of computational techniques, and the observed increase in catalytic activity was corroborated by kinetic data derived from a model reaction. Our investigations led to the discovery of a set of ortho-(sulfonyloxy)benzeneboronic acids that compared favorably with the established state-of-the-art. These newly developed catalysts demonstrated efficacy in the coupling of aliphatic, aromatic, and heteroaromatic acids, as well as primary and secondary amines. Novel boronic acids have been developed for the catalyzed amide synthesis. Lewis acidity estimation using DFT, associated with collected kinetic data, allowed to uncover ortho-(sulfonyloxy)benzeneboronic acids that compared favorably with the established state-of-the-art boronic acids. Efficient coupling of aliphatic, aromatic, and heteroaromatic carboxylic acids as well as primary and secondary amines were obtained.image

Automated summary

This study developed novel boronic acids for catalyzed amide synthesis. The Lewis acidity of the boronic acids was estimated using computational techniques, and the increase in catalytic activity was confirmed with kinetic data. A set of newly developed catalysts were found, which showed superior efficacy in the coupling reaction of acids and amines.