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Copper-catalyzed synthesis of indolyl diketones via C–H oxidation/diacylation of indoles with arylglyoxal hydrates

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Abstract

An expedient protocol for Cu-catalyzed C–H oxidation/diacylation of indoles with arylglyoxal hydrates to construct indolyl diketones is developed. This methodology exhibits the synthetic utility of the synthesis of an indole-alkaloid 1,2-di(1H-indol-3-yl)ethane-1,2-dione and offers a straightforward means to produce different indolyl nitrogen-containing heterocycles such as indolyl quinoxaline, indolyl hydantoin and indolyl imidazole in high yields. Preliminary mechanistic studies indicate that two proposed pathways are involved in this process.

Graphical abstract: Copper-catalyzed synthesis of indolyl diketones via C–H oxidation/diacylation of indoles with arylglyoxal hydrates

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Publication details

The article was received on 22 May 2017, accepted on 30 Jun 2017 and first published on 30 Jun 2017


Article type: Paper
DOI: 10.1039/C7OB01255A
Citation: Org. Biomol. Chem., 2017, Advance Article
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    Copper-catalyzed synthesis of indolyl diketones via C–H oxidation/diacylation of indoles with arylglyoxal hydrates

    C. Wang, Z. Zhang, K. Liu, J. Yan, T. Zhang, G. Lu, Q. Meng, H. Chi and C. Duan, Org. Biomol. Chem., 2017, Advance Article , DOI: 10.1039/C7OB01255A

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