The aromatic nucleophilic substitution (SNAr) between aryl triflates and se
condary amines has been studied. In the absence of solvent, the reaction pr
oceeds at room temperature for nitro and cyano activated aryl triflates and
requires higher temperatures in the case of carboxy activation. Variable t
riflate reactivity could be explained in terms of frontier molecular orbita
l theory. This methodology has been applied for the synthesis of substitute
d piperidyl pyridines.