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. An unprecedented three-component reaction of amines, arynes, and organohalides provides convenient access to structurally diverse tertiary 2-haloanilines.