The task of the presented PhD thesis was the development of new transition-metal catalyzed arylation methods for sp3 C-H bonds of cyclic and acyclic amines. The regioselective C-H activation of the unactivated bond can be achieved by cyclometalation. One of the key steps for this transformation was the introduction of a suitable directing group which can be cleaved after the transformation. Different directing groups as well as different catalytic methods for the direct arylation of benzylic amines were investigated. After intensive screenings, 3-substituted pyridines were found to be the best directing groups. Three different protocols could be established for the direct transformation of benzylic amines. The C-H bond functionalization could be performed with arylboronic acid esters, aryl bromides, and aryl chlorides. Furthermore, mechanistic studies were conducted to obtain a better understanding of the transformation. Finally, the general applicability of this directing group was also demonstrated for the selective mono arylation of piperidines.