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Angewandte Chemie v.130 no.29, 2018년, pp.9231 - 9235  

Palladium(II)‐Catalyzed Enantioselective Arylation of Unbiased Methylene C(sp3)−H Bonds Enabled by a 2‐Pyridinylisopropyl Auxiliary and Chiral Phosphoric Acids

Yan, Sheng‐Yi (Department of Chemistry, Zhejiang University, Hangzhou, 310027, China ) ; Han, Ye‐Qiang (Department of Chemistry, Zhejiang University, Hangzhou, 310027, China ) ; Yao, Qi‐Jun (Department of Chemistry, Zhejiang University, Hangzhou, 310027, China ) ; Nie, Xing‐Liang (Department of Chemistry, Zhejiang University, Hangzhou, 310027, China ) ; Liu, Lei (Department of Chemistry, Zhejiang University, Hangzhou, 310027, China ) ; Shi, Bing‐Feng (Department of Chemistry, Zhejiang University, Hangzhou, 310027, China ) ;
  • 초록  

    Abstract Enantioselective functionalizations of unbiased methylene C(sp 3 )−H bonds of linear systems by metal insertion are intrinsically challenging and remain a largely unsolved problem. Herein, we report a palladium(II)‐catalyzed enantioselective arylation of unbiased methylene β‐C(sp 3 )−H bonds enabled by the combination of a strongly coordinating bidentate PIP auxiliary with a monodentate chiral phosphoric acid (CPA). The synergistic effect between the PIP auxiliary and the non‐ C 2 ‐symmetric CPA is crucial for effective stereocontrol. A broad range of aliphatic carboxylic acids and aryl bromides can be used, providing β‐arylated aliphatic carboxylic acid derivatives in high yields (up to 96 %) with good enantioselectivities (up to 95:5 e.r.). Notably, this reaction also represents the first palladium(II)‐catalyzed enantioselective C−H activation with less reactive and cost‐effective aryl bromides as the arylating reagents. Mechanistic studies suggest that a single CPA is involved in the stereodetermining C−H palladation step.


  • 주제어

    C-H-Aktivierung .   Enantioselektivität .   Kooperative Effekte .   Palladium .   Zweizähnige Auxiliare.  

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