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Palladium-Catalyzed Oxidative Coupling of Aromatic Primary Amines and Alkenes under Molecular Oxygen: Stereoselective Assembly of (Z)-Enamines

Xiaochen Ji, Huawen Huang, Wanqing Wu, Xianwei Li and Huanfeng Jiang*

*School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510640, China, Email: jianghfscut.edu.cn

X. Ji, H. Huang, W. Wu, X. Li, H. Jiang, J. Org. Chem., 2013, 78, 11155-11162.

DOI: 10.1021/jo402117r (free Supporting Information)


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Abstract

An efficient, mild Pd-catalyzed oxidative coupling of aromatic primary amines and alkenes under molecular oxygen provides a rapid access to (Z)-enamines with exceptional functional group tolerance and excellent regio- and stereoselectivity. The resultant enamines could be conveniently transformed into a series of N-containing heterocycles, thus illustrating its potential applications in synthetic and medicinal chemistry.

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Key Words

β-enamino esters, indoles, oxygen


ID: J42-Y2013