Palladium-catalyzed synthesis of arylamines from aryl halides. Mechanistic studies lead to coupling in the absence of tin reagents

The reaction of aryl halides with secondary amines in the presence of silylamide base and tri-o-tolyphopshine palladium complexes gives arylamine products. This process provides a convenient method for performing these hetero-cross coupling reactions without the necessity for forming tin amides and disposing of tin halides. This reaction follows from a mechanistic analysis of the coupling reaction with tin amides and occurs as a result of the cleavage of palladium aryl halide dimers with secondary amines.