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Issue 2, 2016
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Boronic acid–DMAPO cooperative catalysis for dehydrative condensation between carboxylic acids and amines

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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

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Supplementary files

Article information


Submitted
04 Oct 2015
Accepted
02 Nov 2015
First published
06 Nov 2015

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2016,7, 1276-1280
Article type
Edge Article
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

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