Palladium-Catalyzed Synthesis of Arylamines from Aryl Halides. Mechanistic Studies Lead to Coupling in the Absence of Tin Reagents

Article abstract of DOI:10.1016/0040-4039(95)00605-C

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 heterocross 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.