Issue 2, 2016

Boronic acid–DMAPO cooperative catalysis for dehydrative condensation between carboxylic acids and amines

Abstract

Arylboronic acid and 4-(N,N-dimethylamino)pyridine N-oxide (DMAPO) cooperatively catalyse the dehydrative condensation reaction between carboxylic acids and amines to give the corresponding amides under azeotropic reflux conditions. This cooperative use is much more effective than their individual use as catalysts, and chemoselectively promotes the amide condensation of (poly)conjugated carboxylic acids. The present method is practical and scalable, and has been applied to the synthesis of sitagliptin and a drug candidate.

Graphical abstract: Boronic acid–DMAPO cooperative catalysis for dehydrative condensation between carboxylic acids and amines

Supplementary files

Article information

Article type
Edge Article
Submitted
04 ต.ค. 2558
Accepted
02 พ.ย. 2558
First published
06 พ.ย. 2558
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2016,7, 1276-1280

Author version available

Boronic acid–DMAPO cooperative catalysis for dehydrative condensation between carboxylic acids and amines

K. Ishihara and Y. Lu, Chem. Sci., 2016, 7, 1276 DOI: 10.1039/C5SC03761A

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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