1,2-Aminohalogenation of arynes with amines and organohalides.

An unprecedented use of inexpensive organohalides as halogen electrophiles to trap the zwitterion intermediates generated from amines and arynes has been developed to access structurally diverse tertiary 2-haloanilines. Effective organohalides include carbon tetrachloride, hexachloroethane, N-chlorosuccinimide, carbon tetrabromide, fluorotribromomethane, N-bromosuccinimide, carbon tetraiodide, and N-iodosuccinimide.