Copper-catalyzed direct amination of quinoline N-oxides via C-H bond activation under mild conditions

Chongwei Zhu; Meiling Yi; Donghui Wei; Xuan Chen; Yangjie Wu; Xiuling Cui

doi:10.1021/ol500183w

Copper-catalyzed direct amination of quinoline N-oxides via C-H bond activation under mild conditions

Org Lett. 2014 Apr 4;16(7):1840-3. doi: 10.1021/ol500183w. Epub 2014 Mar 14.

Authors

Chongwei Zhu¹, Meiling Yi, Donghui Wei, Xuan Chen, Yangjie Wu, Xiuling Cui

Affiliation

¹ Department of Chemistry, Henan Key Laboratory of Chemical Biology and Organic Chemistry, Key Laboratory of Applied Chemistry of Henan Universities, Zhengzhou University , Zhengzhou 450052, P. R. China.

PMID: 24628081
DOI: 10.1021/ol500183w

Abstract

A highly efficient and concise one-pot strategy for the direct amination of quinoline N-oxides via copper-catalyzed dehydrogenative C-N coupling has been developed. The desired products were obtained in good to excellent yields for 22 examples starting from the parent aliphatic amines. This methodology provides a practical pathway to 2-aminoquinolines and features a simple system, high efficiency, environmental friendliness, low reaction temperature, and ligand, additives, base, and external oxidant free conditions.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Amination
Aminoquinolines / chemical synthesis*
Aminoquinolines / chemistry
Catalysis
Copper / chemistry*
Molecular Structure
Oxides / chemistry*

Substances

Aminoquinolines
Oxides
Copper