Copper-catalyzed coupling of anthranils and α-keto acids: direct synthesis of α-ketoamides

Ping-Gui Li; Hao Zhu; Min Fan; Cheng Yan; Kai Shi; Xi-Wen Chi; Liang-Hua Zou

doi:10.1039/C9OB00822E

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Copper-catalyzed coupling of anthranils and α-keto acids: direct synthesis of α-ketoamides†

Ping-Gui Li,‡^ab Hao Zhu,

‡^a Min Fan,^a Cheng Yan,^a Kai Shi,^a Xi-Wen Chi^a and Liang-Hua Zou

*^a

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* Corresponding authors

^a The Key Laboratory of Carbohydrate Chemistry and Biotechnology, Ministry of Education, School of Pharmaceutical Sciences, Jiangnan University, Lihu Avenue 1800, Wuxi 214122, P.R. China

^b State Key Laboratory of Coordination Chemistry, School of Chemistry and Chemical Engineering, Nanjing University, Xianlin Avenue 163, Nanjing 210093, China

Abstract

Copper-catalyzed coupling of α-keto acids with anthranils is reported for the synthesis of α-ketoamides. This process involves N–O/C–O bond cleavages and C–N bond formation. Furthermore, the decarboxylation of α-keto acids can be successfully suppressed under redox-neutral conditions.

This article is part of the themed collection: Synthetic methodology in OBC

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DOI: https://doi.org/10.1039/C9OB00822E
Article type: Communication
Submitted: 10 Apr 2019
Accepted: 20 May 2019
First published: 21 May 2019

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Org. Biomol. Chem., 2019,17, 5902-5907

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Copper-catalyzed coupling of anthranils and α-keto acids: direct synthesis of α-ketoamides

P. Li, H. Zhu, M. Fan, C. Yan, K. Shi, X. Chi and L. Zou, Org. Biomol. Chem., 2019, 17, 5902 DOI: 10.1039/C9OB00822E

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Organic & Biomolecular Chemistry

Copper-catalyzed coupling of anthranils and α-keto acids: direct synthesis of α-ketoamides†

Abstract

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Copper-catalyzed coupling of anthranils and α-keto acids: direct synthesis of α-ketoamides

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