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One-Pot, Metal-Free Conversion of Anilines to Aryl Bromides and Iodides
A metal-free
synthesis of aryl bromides and iodides from anilines
via halogen abstraction from bromotrichloromethane and diiodomethane
is described. This one-pot reaction affords aryl halides from the
corresponding anilines in moderate to excellent yields without isolation
of diazonium salts. The transformation has short reaction times, a
simple workup, and insensitivity to moisture and air and avoids excess
halogenation. DFT calculations support a S<sub>RN</sub>1 mechanism.
This method represents a convenient alternative to the classic Sandmeyer
reaction