Intramolecular Palladium-Catalyzed Oxidative Amination of Furans: Synthesis of Functionalized Indoles

Anton S. Makarov; Maxim G. Uchuskin; Vladimir Gevorgyan

doi:10.1021/acs.joc.8b02470

Intramolecular Palladium-Catalyzed Oxidative Amination of Furans: Synthesis of Functionalized Indoles

Anton S. Makarov, Maxim G. Uchuskin, Vladimir Gevorgyan

Research output: Contribution to journal › Article › peer-review

13 Scopus citations

Abstract

Unconventional modification of palladium-catalyzed oxidative amination where a furan ring serves as a masked olefin is described. The designed chemical process provides 2-(2-acylvinyl)indole derivatives with up to a 93% yield and excellent E-selectivity. A highly reactive α,β-unsaturated carbonyl moiety of the obtained compounds allows for accessing various heteroaromatic scaffolds through simple synthetic procedures.

Original language	English (US)
Pages (from-to)	14010-14021
Number of pages	12
Journal	Journal of Organic Chemistry
Volume	83
Issue number	22
DOIs	https://doi.org/10.1021/acs.joc.8b02470
State	Published - Nov 16 2018
Externally published	Yes

ASJC Scopus subject areas

Organic Chemistry

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10.1021/acs.joc.8b02470

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abstract = "Unconventional modification of palladium-catalyzed oxidative amination where a furan ring serves as a masked olefin is described. The designed chemical process provides 2-(2-acylvinyl)indole derivatives with up to a 93% yield and excellent E-selectivity. A highly reactive α,β-unsaturated carbonyl moiety of the obtained compounds allows for accessing various heteroaromatic scaffolds through simple synthetic procedures.",

author = "Makarov, {Anton S.} and Uchuskin, {Maxim G.} and Vladimir Gevorgyan",

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T2 - Synthesis of Functionalized Indoles

AU - Makarov, Anton S.

AU - Uchuskin, Maxim G.

AU - Gevorgyan, Vladimir

PY - 2018/11/16

Y1 - 2018/11/16

N2 - Unconventional modification of palladium-catalyzed oxidative amination where a furan ring serves as a masked olefin is described. The designed chemical process provides 2-(2-acylvinyl)indole derivatives with up to a 93% yield and excellent E-selectivity. A highly reactive α,β-unsaturated carbonyl moiety of the obtained compounds allows for accessing various heteroaromatic scaffolds through simple synthetic procedures.

AB - Unconventional modification of palladium-catalyzed oxidative amination where a furan ring serves as a masked olefin is described. The designed chemical process provides 2-(2-acylvinyl)indole derivatives with up to a 93% yield and excellent E-selectivity. A highly reactive α,β-unsaturated carbonyl moiety of the obtained compounds allows for accessing various heteroaromatic scaffolds through simple synthetic procedures.

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Intramolecular Palladium-Catalyzed Oxidative Amination of Furans: Synthesis of Functionalized Indoles

Abstract

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