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钯催化通过一锅法N-芳基化和氧化联芳基偶联直接合成咔唑:合成与机理研究

Palladium-catalyzed direct synthesis of carbazoles via one-pot N-arylation and oxidative biaryl coupling: synthesis and mechanistic study.

作者信息

Watanabe Toshiaki, Oishi Shinya, Fujii Nobutaka, Ohno Hiroaki

机构信息

Graduate School of Pharmaceutical Sciences, Kyoto University, Sakyo-ku, Kyoto 606-8501, Japan.

出版信息

J Org Chem. 2009 Jul 3;74(13):4720-6. doi: 10.1021/jo9003376.

Abstract

An efficient catalytic system has been developed for the synthesis of carbazoles by one-pot N-arylation and oxidative biaryl coupling. A significant substituent effect of the diarylamine intermediate on oxidative coupling was observed. Mechanistic studies of oxidative coupling, including trapping of reaction intermediates and kinetic isotope effect experiments, are also presented.

摘要

已经开发出一种高效的催化体系,用于通过一锅法N-芳基化和氧化联芳基偶联来合成咔唑。观察到二芳基胺中间体对氧化偶联有显著的取代基效应。还介绍了氧化偶联的机理研究,包括反应中间体的捕获和动力学同位素效应实验。

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