Chem. J. Chinese Universities

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Synthesis, Characterization and Catalytic Activity of Cyclopalladated Ferrocenylimine Carbene Complex in Buchwald-Hartwig Amination

LI Jing-Ya, WU Yang-Jie*, HAN Zi-Xing, JIANG Song   

  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, China
  • Received:2008-02-16 Revised:1900-01-01 Online:2008-08-10 Published:2008-08-10
  • Contact: WU Yang-Jie

Abstract: The palladium-catalyzed amination of aryl halides(Buchwald-Hartwig amination) is a rapidly developing field due to the importance of the products in many fields, e.g. pharmaceuticals, xerography, electronic materials and ligands for transition metals. In this article, a novel cyclopalladated ferrocenylimine carbene complex 3 was conveniently synthesized and characterized via IR, 1H NMR, 13C NMR, HRMS and X-ray single crystal diffraction. Compound 3 was stable to air and moisture in both the solid state and solution. It was successfully applied for the Buchwald-Hartwig amination of aryl chlorides. Using 0.5%(molar fraction) of catalyst 3, in the presence of 2 equiv of tBuOK as a base in dioxane at 110 ℃ for 3 h, a variety of aryl chlorides and amines could be coupled to afford the coupled products in moderate or excellent yields.

Key words: Cycllopalladated ferrocenylimine, N-Heterocyclic carbene, Amination, Aryl chlorides

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