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

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.