Oxidative C−H/C−H Cross‐Coupling Reactions between N‐Acylanilines and Benzamides Enabled by a Cp*‐Free RhCl3/TFA Catalytic System,Angewandte Chemie International Edition

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Oxidative C−H/C−H Cross‐Coupling Reactions between N‐Acylanilines and Benzamides Enabled by a Cp*‐Free RhCl3/TFA Catalytic System
Angewandte Chemie International Edition ( IF 16.1 ) Pub Date : 2018-06-19 , DOI: 10.1002/anie.201804528
Yang Shi ₁ , Luoqiang Zhang ₁ , Jingbo Lan ₁ , Min Zhang ₁ , Fulin Zhou ₁ , Wenlong Wei ₁ , Jingsong You ₁

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By making use of a dual‐chelation‐assisted strategy, a completely regiocontrolled oxidative C−H/C−H cross‐coupling reaction between an N‐acylaniline and a benzamide has been accomplished for the first time. This process constitutes a step‐economic and highly efficient pathway to 2‐amino‐2′‐carboxybiaryl scaffolds from readily available substrates. A Cp*‐free RhCl₃/TFA catalytic system was developed to replace the [Cp*RhCl₂]₂/AgSbF₆ system generally used in oxidative C−H/C−H cross‐coupling reactions between two (hetero)arenes (Cp*=pentamethylcyclopentadienyl, TFA=trifluoroacetic acid). The RhCl₃/TFA system avoids the use of the expensive Cp* ligand and AgSbF₆. As an illustrative example, the procedure developed herein greatly streamlines the total synthesis of the naturally occurring benzo[c]phenanthridine alkaloid oxynitidine, which was accomplished in excellent overall yield.

中文翻译：

无Cp *的RhCl3 / TFA催化系统在N-酰基苯胺和苯甲酰胺之间的氧化CH-H / C-H交叉偶联反应

通过使用双重螯合辅助策略，首次实现了N-丙氨酸与苯甲酰胺之间完全区域控制的氧化CH / C-H交叉偶联反应。此过程构成了从容易获得的底物制备2-氨基2'-羧基联芳基支架的经济高效的步骤。开发了无Cp *的RhCl ₃ / TFA催化体系来代替通常用于两个（杂）芳烃（Cp）的氧化CH / CH交叉偶联反应中的[Cp * RhCl ₂ ] ₂ / AgSbF ₆体系* ＝五甲基环戊二烯基，TFA ＝三氟乙酸）。RhCl ₃ / TFA系统避免使用昂贵的Cp *配体和AgSbF ₆。作为说明性实例，本文开发的方法极大地简化了天然存在的苯并[ c ]菲啶生物碱氧基亚硝胺的总合成，这以优异的总收率实现。

更新日期：2018-06-19

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