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Angewandte Chemie v.130 no.29, 2018년, pp.9246 - 9250  

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

Shi, Yang (Key Laboratory of Green Chemistry and Technology of Ministry of Education, College of Chemistry, Sichuan University, 29 Wangjiang Road, Chengdu, 610064, P. R. China ) ; Zhang, Luoqiang (Key Laboratory of Green Chemistry and Technology of Ministry of Education, College of Chemistry, Sichuan University, 29 Wangjiang Road, Chengdu, 610064, P. R. China ) ; Lan, Jingbo (Key Laboratory of Green Chemistry and Technology of Ministry of Education, College of Chemistry, Sichuan University, 29 Wangjiang Road, Chengdu, 610064, P. R. China ) ; Zhang, Min (Key Laboratory of Green Chemistry and Technology of Ministry of Education, College of Chemistry, Sichuan University, 29 Wangjiang Road, Chengdu, 610064, P. R. China ) ; Zhou, Fulin (Key Laboratory of Green Chemistry and Technology of Ministry of Education, College of Chemistry, Sichuan University, 29 Wangjiang Road, Chengdu, 610064, P. R. China ) ; Wei, Wenlong ; You, Jingsong ;
  • 초록  

    Abstract 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 RhCl 3 /TFA catalytic system was developed to replace the [Cp*RhCl 2 ] 2 /AgSbF 6 system generally used in oxidative C−H/C−H cross‐coupling reactions between two (hetero)arenes (Cp*=pentamethylcyclopentadienyl, TFA=trifluoroacetic acid). The RhCl 3 /TFA system avoids the use of the expensive Cp* ligand and AgSbF 6 . 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.


  • 주제어

    C-H-Aktivierung .   Duale Chelatisierung .   Rhodium-Katalyse .   Oxidative Kreuzkupplungen .   Oxynitidin.  

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