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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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Publication details

The article was received on 04 Oct 2015, accepted on 02 Nov 2015 and first published on 06 Nov 2015


Article type: Edge Article
DOI: 10.1039/C5SC03761A
Citation: Chem. Sci., 2016,7, 1276-1280
  • Open access: Creative Commons BY license
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    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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