Organic Chemistry Portal



Construction of Nitrogen Heterocycles Bearing an Aminomethyl Group by Copper-Catalyzed Domino Three-Component Coupling-Cyclization

Yusuke Ohta, Hiroaki Chiba, Shinya Oishi, Nobutaka Fujii* and Hiroaki Ohno*

*Graduate School of Pharmaceutical Sciences, Kyoto University, Sakyo-ku, Kyoto 606-8501, Japan, Email:,

Y. Ohta, H. Chiba, S. Oishi, N. Fujii, H. Ohno, J. Org. Chem., 2009, 74, 7052-7058.

DOI: 10.1021/jo901328q

see article for more reactions


2-Ethynylanilines were converted to various substituted 2-(aminomethyl)indoles in good to excellent yields in the presence of a secondary amine and an aldehyde by a copper-catalyzed domino three-component coupling-cyclization. Utilizing this domino reaction and C-H functionalization at the indole C-3 position, polycyclic indoles were readily synthesized.

see article for more examples

Key Words

Indoles, Multicomponent Reactions

ID: J42-Y2009-2730