Compounds containing the iminodibenzyl and iminostilbene ring systems are prevalent in medicinal targets and functional materials.Herein we report palladium catalyzed conditions for the N-arylation of these ring systems.This protocol could be applied to a variety of (hetero)aryl chloride and bromide substrates, including ones which are sterically hindered or those containing a variety of functional groups.Use of the fourth generation palladacycle precatalyst allowed good to excellent yields to be obtained using low palladium catalyst loadings (0.1 to 1 mol%).