Ligand‐Controlled Copper‐Catalyzed Highly Regioselective Difluoromethylation of Allylic Chlorides/Bromides and Propargyl Bromides

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  • Yang Gu
    Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry University of Chinese Academy Sciences, Chinese Academy of Sciences, 345 Lingling Road Shanghai 200032 China
  • Changhui Lu
    Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry University of Chinese Academy Sciences, Chinese Academy of Sciences, 345 Lingling Road Shanghai 200032 China
  • Yucheng Gu
    Syngenta, Jealott's Hill International Research Cente Bracknell Berkshire RG42 6EY UK
  • Qilong Shen
    Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry University of Chinese Academy Sciences, Chinese Academy of Sciences, 345 Lingling Road Shanghai 200032 China

抄録

<jats:p>Highly regiodivergent copper‐catalyzed allylic/propargylic difluoromethylation reactions by employing different ligands are described. When 5,6‐dimethyl‐1,10‐phenanthroline was used as the ligand, exclusively α‐difluoromethylated products were obtained, while γ‐selective difluoromethylated products were generated when <jats:italic>N</jats:italic>‐heterocyclic carbene‐SIPr was used as the ligand. Likewise, high α‐ vs. γ‐selectivities were achieved in the presence of similar copper catalysts for the reactions of propargyl bromides. Moreover, a copper‐catalyzed asymmetric allylic difluoromethylation reaction with moderate to good enantioselectivity by the use of chiral ligands was developed.</jats:p>

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