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Issue 18, 2016
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Clean synthesis of primary to tertiary carboxamides by CsOH-catalyzed aminolysis of nitriles in water

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Abstract

Using CsOH as the only catalyst and utilizing its “cesium effect”, a clean synthesis of a wide range of primary, secondary, and tertiary carboxamides was achieved by aminolysis reactions of nitriles with ammonia, primary, or secondary amines in water. Studies on the control reactions revealed that the reactions with ammonia most probably proceed via an aminolysis path by the initial addition of ammonia to Cs-activated nitriles to form unsubstituted amidine intermediates, while the reactions with primary or secondary amines may proceed via a hydration/transamidation path by the initial hydration of the Cs-activated nitriles to form primary carboxamide intermediates followed by their transamidation with amines through the formation of substituted amidine intermediates.

Graphical abstract: Clean synthesis of primary to tertiary carboxamides by CsOH-catalyzed aminolysis of nitriles in water

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Publication details

The article was received on 08 Jun 2016, accepted on 27 Jul 2016 and first published on 27 Jul 2016


Article type: Communication
DOI: 10.1039/C6GC01565D
Citation: Green Chem., 2016,18, 4865-4870
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    Clean synthesis of primary to tertiary carboxamides by CsOH-catalyzed aminolysis of nitriles in water

    Y. Li, H. Chen, J. Liu, X. Wan and Q. Xu, Green Chem., 2016, 18, 4865
    DOI: 10.1039/C6GC01565D

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