Simple Amine-Directed Meta-Selective C-H Arylation via Pd/Norbornene Catalysis
Simple Amine-Directed Meta-Selective C-H Arylation via Pd/Norbornene Catalysis
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DOI：
10.1021/jacs.5b02809
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发表时间：
2015-05-13
影响因子：
15
通讯作者：
Dong, Guangbin
中科院分区：
文献类型：
--
作者：
Dong, Zhe;Wang, Jianchun;Dong, Guangbin
在此，我们报道了一种以简单叔胺为导向基团的高度异位选择性的C-H芳基化反应。该方法利用Pd/降冰片烯的催化作用，提供了一种独特的控制中心选择性的策略。以市售AsPh3为配体和一种独特的“醋酸酯鸡尾酒”促进了该反应。以含邻位电子抽提基团的芳基碘化物为偶联对。在反应条件下，可以容忍广泛的官能团，包括一些杂芳烃。此外，胺导向基团可以很容易地安装并转化为其他常见的多功能官能团。我们希望这种C-H功能化模式对开发本工作以外的其他元选择转换具有广泛的意义。
Herein we report a highly meta-selective C-H arylation using simple tertiary amines as the directing group. This method takes advantage of Pd/norbornene catalysis, offering a distinct strategy to control the site selectivity. The reaction was promoted by commercially available AsPh3 as the ligand and a unique "acetate cocktail". Aryl iodides with an ortho electron-withdrawing group were employed as the coupling partner. A wide range of functional groups, including some heteroarenes, are tolerated under the reaction conditions. In addition, the amine directing group can be easily installed and transformed to other common versatile functional groups. We expect this C-H functionalization mode to have broad implications for developing other meta-selective transformations beyond this work.