The 1,5,6,7,8,8a-hexahydroimidazo[1,5-a]pyridine, 3, was quaternized with 2-(bromomethyl-1,3,5-trimethylbenzene, 1,4-bis(bromomethyl)-2,3,5,6-tetramethylbenzene, 2,4-bis(bromomethyl)-1,3,5-trimethylbenzene, 1,3,5-tris(bromomethyl)-2,4,6-trimethylbenzene and 1,3,5-tris(bromomethyl)-2,4,6-triethylbenzene to obtain mono-, bis-and tris-imidazolinium salts (4-7) which were characterized by elemental analysis and NMR spectroscopy. In order to understand the effects of these changes on the N-substituent and how they translate to catalytic activity, these new salts (4-7) with Pd(OAc) 2 were applied as in situ catalysts for Suzuki-Miyaura and Heck-Mirozoki cross-coupling reactions of aryl chlorides and aryl bromides, respectively. The tris-imidazolinium salts (7) were found to be more efficient than the related analogs 4-6.