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Issue 3, 2017
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Zinc-catalyzed chemoselective alkylation of α-keto amides with 2-alkylazaarenes

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Abstract

A zinc-catalyzed C(sp3)–H addition of 2-alkylazaarenes to α-keto amides to furnish azaarene incorporated α-hydroxy amides has been developed with a wide range of substrates in moderate to excellent yields, respectively. Chemoselective alkylation of the keto functionality of the α-keto amides in the presence of simple ketones is the key advantage of this Zn-catalyzed transformation. This approach has been demonstrated to one gram-scale synthesis. 1H NMR and D2O exchange experimental studies reveal that the reaction proceeds through a Zn-enamide intermediate.

Graphical abstract: Zinc-catalyzed chemoselective alkylation of α-keto amides with 2-alkylazaarenes

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Supplementary files

Article information


Submitted
08 Nov 2016
Accepted
12 Dec 2016
First published
12 Dec 2016

Org. Biomol. Chem., 2017,15, 691-700
Article type
Paper

Zinc-catalyzed chemoselective alkylation of α-keto amides with 2-alkylazaarenes

A. Muthukumar and G. Sekar, Org. Biomol. Chem., 2017, 15, 691
DOI: 10.1039/C6OB02432G

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