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Chemoselective C(α)–C(β) bond cleavage of saturated aryl ketones with amines leading to α-ketoamides: a copper-catalyzed aerobic oxidation process with air

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Abstract

An unprecedented selective C(α)–C(β) bond cleavage of simple saturated aryl ketones was developed. The corresponding α-ketoamides, ubiquitous structural units in a variety of natural products, were constructed from copper-catalyzed aerobic oxidative C–C bond cleavage and amidation of ketones with amines under air. And this reaction featured simple starting materials and a broad substrate scope. Moreover, no obvious limitation was observed in terms of a gram-scale application. In addition, a plausible reaction pathway was proposed based on mechanism studies.

Graphical abstract: Chemoselective C(α)–C(β) bond cleavage of saturated aryl ketones with amines leading to α-ketoamides: a copper-catalyzed aerobic oxidation process with air

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Publication details

The article was received on 04 Aug 2017, accepted on 30 Aug 2017 and first published on 31 Aug 2017


Article type: Research Article
DOI: 10.1039/C7QO00690J
Citation: Org. Chem. Front., 2017, Advance Article
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    Chemoselective C(α)–C(β) bond cleavage of saturated aryl ketones with amines leading to α-ketoamides: a copper-catalyzed aerobic oxidation process with air

    C. Liu, Z. Yang, Y. Zeng, Z. Fang and K. Guo, Org. Chem. Front., 2017, Advance Article , DOI: 10.1039/C7QO00690J

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