Hemilabile-coordinated copper promoted amination of aryl halides with ammonia in aqueous ethylene glycol under atmosphere pressure

Direct amination of aryl iodides and bromides with ammonia under 1 atm pressure has been effected using in situ-generated hemilabile coordinated copper(l) species from copper(l) halides or copper metal in aqueous ethylene glycol, producing primary aromatic amines in good yields. Ammonia pressure and water were found to accelerate the copper-mediated reaction while strong chelating ligands showed a suppression effect. A rationale for the copper-mediated amination of aryl halides with ammonia is given based on a double-face role of chelating effect. Copyright (C) 2009 John Wiley & Sons, Ltd.