Synthesis of anilines and di- and triarylamines by palladium-catalyzed coupling of aryl halides and ammonia

ORGN 294

David S. Surry, dsurry@mit.edu and Stephen L. Buchwald, sbuchwal@MIT.EDU. Department of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Avenue, Cambridge, MA 02139
Aromatic amines are an important group of compounds, in particular triarylamines have been the subject of intensive research due to their applications in optoelectronics and xerography. There is no efficient method to make such substances directly from aryl chlorides and ammonia, despite the low cost of these starting materials. We have developed a palladium-catalyzed coupling of aryl chlorides and ammonia using monophospine ligands that allows anilines and di- or triarylamines to be formed selectively by adjustment of reaction conditions. Moreover, by sequential addition of different aryl chlorides to the reaction mixture unsymmetrical triarylamines may be made in a one-pot procedure. This method is likely to have numerous uses in materials science and pharmaceutical research.