Palladium(II)‐Catalyzed Enantioselective Arylation of Unbiased Methylene C(sp<sup>3</sup>)−H Bonds Enabled by a 2‐Pyridinylisopropyl Auxiliary and Chiral Phosphoric Acids

DOI Web Site Web Site 被引用文献9件
  • Sheng‐Yi Yan
    Department of Chemistry Zhejiang University Hangzhou 310027 China
  • Ye‐Qiang Han
    Department of Chemistry Zhejiang University Hangzhou 310027 China
  • Qi‐Jun Yao
    Department of Chemistry Zhejiang University Hangzhou 310027 China
  • Xing‐Liang Nie
    Department of Chemistry Zhejiang University Hangzhou 310027 China
  • Lei Liu
    Department of Chemistry Zhejiang University Hangzhou 310027 China
  • Bing‐Feng Shi
    Department of Chemistry Zhejiang University Hangzhou 310027 China

書誌事項

公開日
2018-06-19
権利情報
  • http://onlinelibrary.wiley.com/termsAndConditions#vor
DOI
  • 10.1002/anie.201804197
公開者
Wiley

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<jats:title>Abstract</jats:title><jats:p>Enantioselective functionalizations of unbiased methylene C(sp<jats:sup>3</jats:sup>)−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<jats:sup>3</jats:sup>)−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‐<jats:italic>C</jats:italic><jats:sub>2</jats:sub>‐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.</jats:p>

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