Issue 2, 2019

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

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

Supplementary files

Article information

Article type
Paper
Submitted
15 Nov 2018
Accepted
06 Dec 2018
First published
08 Dec 2018

Org. Biomol. Chem., 2019,17, 309-314

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, 17, 309 DOI: 10.1039/C8OB02844C

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