 The first generation (Pd[P(o-Tolyl)3]2) catalyst system was found to be effective for the coupling of both cyclic and acyclic secondary amines bearing both alkyl and aryl functionality (though not diarylamines) with a variety of aryl bromides.In general, these conditions were not able to couple primary amines due to competitive hydrodehalogenation of the arene.Aryl iodides were found to be suitable substrates for the intramolecular variant of this reaction, and importantly, could be coupled intermolecularly only if dioxane was used in place of toluene as a solvent, albeit with modest yields.