The Bamberger Reaction in Hydrogen Fluoride: The Use of Mild Reductive Metals for the Preparation of Fluoroaromatic Amines.

Abstract The reduction of nitroaromatic compounds by various metals (tin, lead, bismuth) in liquid hydrogen fluoride under an inert atmosphere leads to fluoroaromatic amines, in accord with the Bamberger reaction. Generally, a co-solvent such as pentane or methylene chloride is used. Some non-fluorinated arylamines are also formed by a competitive direct reduction of the N -arylhydroxylamine intermediate. Of the mild reductive metals studied, bismuth was the most selective.