4.7 Article

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

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 78, Issue 22, Pages 11155-11162

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/jo402117r

Keywords

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Funding

  1. National Basic Research Program of China (973 Program) [2011CB808600]
  2. National Nature Science Foundation of China [20932002, 21172076, 21202046]
  3. Changjiang Scholars and Innovation Team Project of Ministry of Education
  4. Guangdong Natural Science Foundation [10351064101000000, S2012040007088]

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An efficient Pd-catalyzed oxidative coupling of aromatic primary amines and alkenes under molecular oxygen is disclosed. Under mild reaction conditions, it provides a rapid access to (Z)-enamine compounds with exceptional functional group tolerance and excellent regio- and stereoselectivity. This attractive route is of great significance due to its applicability to a wide range of aromatic primary amines, most of which could not be efficiently converted into enamines previously. Moreover, this protocol is scalable, and the resultant enamines could be conveniently transformed into a series of N-containing heterocyclics, thus illustrating its potential applications in synthetic and medicinal chemistry.

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