Formal Insertion of Imines (or Nitrogen Heteroarenes) and Arynes into the C-Cl Bond of Carbon Tetrachloride

Organic Letters
Sheng-Jun LiZhi-Xiang Yu

Abstract

The formal insertion of double and triple bonds into the C-Cl bond of carbon tetrachloride has enabled the full utilization of carbon tetrachloride in chemical synthesis. A range of unactivated imines and electron-deficient nitrogen heteroarenes served as effective sources of C=N bonds to react with arynes and carbon tetrachloride to afford functionalized anilines whose core structures are present in some valuable arthropodicides. Control experiments and DFT calculations suggest the involvement of a trichloromethyl anion intermediate.

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Citations

Sep 3, 2019·Chemical Communications : Chem Comm·Sheng-Jun LiShi-Kai Tian
Sep 27, 2019·Chemical Communications : Chem Comm·Yu ZhangHuanfeng Jiang
Sep 19, 2019·Angewandte Chemie·Daniel B Werz, Akkattu T Biju

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