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Cu-Catalyzed carbamoylation versus amination of quinoline N-oxide with formamides

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Abstract

An efficient, direct carbamoylation and amination of quinoline N-oxides with formamides to access 2-carbamoyl and 2-amino quinolines has been developed through copper-catalyzed C–C and C–N bond formations via cross-dehydrogenative coupling reactions. The reaction proceeds smoothly over a broad range of substrates with excellent functional group tolerance under mild conditions. Mechanistic studies suggest that the reaction is initiated by formamide radical or decarbonylative aminyl radical formation in the presence of TBHP, according to the different substituent on the N atom of formamide.

Graphical abstract: Cu-Catalyzed carbamoylation versus amination of quinoline N-oxide with formamides

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Publication details

The article was received on 15 Nov 2018, accepted on 06 Dec 2018 and first published on 08 Dec 2018


Article type: Paper
DOI: 10.1039/C8OB02844C
Citation: Org. Biomol. Chem., 2019, Advance Article
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    Cu-Catalyzed carbamoylation versus amination of quinoline N-oxide with formamides

    Y. Zhang, S. Zhang, G. Xu, M. Li, C. Tang and W. Fan, Org. Biomol. Chem., 2019, Advance Article , DOI: 10.1039/C8OB02844C

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