Palladium-catalyzed C-N bond-forming cross-coupling reaction of N-trimethylsilylamines with aryl bromides and chlorides is found to proceed in the presence of a fluoride activator in 1,3-dimethyl-2-imidazolidinone (DMI), giving triarylamines in excellent yields. When aryl bromide and bis(silyl)amine were used in this reaction, double C-N bond-forming products were obtained in high yields. The present reaction was successfully applied to C-N bond-forming polymerization.