Buchwald-Hartwig交叉偶联反应

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  • 概要

钯催化下胺与芳卤的交叉偶联反应，形成胺的N-芳基化产物。该反应是合成芳胺的重要方法。胺可为伯胺或者仲胺，拟芳卤三氟甲磺酸的酚酯（ArOTf）也可用。

  • 反应机理

该反应可能的机理如上面两图所示。以1-溴-4-叔丁基苯和吡咯为例。首先1-溴-4-叔丁基苯与零价LnPd(0)氧化加成生成Pd(II)络合物，随后Pd(II)络合物与吡咯经过配体交换得到中间体，紧接着中间体发生还原消除生成目标化合物，LnPd(0)在这一步中得到循环。

  • 反应实例

Buchwald-Hartwig交叉偶联反应在天然产物和生理活性化合物以及荧光发光体分子合成中得到广泛应用。该反应还可以拓展到芳醚，特别是二芳醚的合成。

  • 参考文献

[1]  Wolfe, J. P.; Wagaw, S.; Buchwald, S. L. J. Am. Chem. Soc., 1996, 118, 7215.

[2]  Driver, M. S.; Hartwig, J. F. J. Am. Chem. Soc. 1996, 118, 7217.

[3]  Wolfe, J. P.; Wagaw, S.; Marcoux, J. -F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805.

[4]  Hartwig, J. F. Angew. Chem., Int. Ed. 1998, 37, 2046.


本文参考自《有机人名反应、试剂与规则》，黄培强主编，与《NameReactions A Collection of Detailed Mechanisms and Synthetic Applications, 5thEdition》，JieJack Li主编。



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