Copper-Catalyzed Hydrodefluorination of Fluoroarenes by Copper Hydride Intermediates

Authors

  • Hongbin Lv,

    1. Beijing National Laboratory for Molecular Sciences, State Key Laboratory of Rare Earth Materials Chemistry and Applications, College of Chemistry and Molecular Engineering, Peking University, Beijing 100871 (P.R. China) http://www.chem.pku.edu.cn/zhangjl/
    Search for more papers by this author
  • Yuan-Bo Cai,

    1. Beijing National Laboratory for Molecular Sciences, State Key Laboratory of Rare Earth Materials Chemistry and Applications, College of Chemistry and Molecular Engineering, Peking University, Beijing 100871 (P.R. China) http://www.chem.pku.edu.cn/zhangjl/
    Search for more papers by this author
  • Prof. Dr. Jun-Long Zhang

    Corresponding author
    1. Beijing National Laboratory for Molecular Sciences, State Key Laboratory of Rare Earth Materials Chemistry and Applications, College of Chemistry and Molecular Engineering, Peking University, Beijing 100871 (P.R. China) http://www.chem.pku.edu.cn/zhangjl/
    • Beijing National Laboratory for Molecular Sciences, State Key Laboratory of Rare Earth Materials Chemistry and Applications, College of Chemistry and Molecular Engineering, Peking University, Beijing 100871 (P.R. China) http://www.chem.pku.edu.cn/zhangjl/

    Search for more papers by this author

  • This project was supported by the National Key Basic Research Support Foundation of China (NKBRSFC) (2010CB912302) and National Scientific Foundation of China (grant no. 20971007).

Abstract

original image

Breaking bad: Efficient copper-catalyzed C[BOND]F bond activation has been achieved by replacing fluorine with hydrogen. A copper hydride is proposed as the active intermediate, which proceeds through a nucleophilic attack on the fluorocarbon, as determined by experimental and theoretical results (see structure; C gray, H white, Cu light red, F light blue; distances in Å).

Ancillary