The previously reported palladium-catalyzed silylation of aryl chlorides with silylsilatranes were theoretically reinvestigated by DFT calculations with a focus on the effect of the transannular Si–N coordination on silyl transfer. The Si–N coordination proved to be not so influential as to accelerate the silyl transfer. However, it should be of benefit to use silylsilatranes as silylating agents because of their easy handling and facile preparation.