A three-part experiment that leads to the synthesis of palladium(II) complex starting from a C[subscript 3]-symmetric triaminoguanidinium-based ligand is presented. In the first part, the preparation of tris-benzylidenetriaminoguanidinium chloride ([H[subscript 6]Br[subscript 3]L]Cl) by an acidic catalyzed 3-fold imine formation reaction of 5-bromo-2-hydroxybenzaldehyde and triaminoguanidinium chloride is described. Starting from the second part, the reaction procedures are performed under inert gas atmosphere. The conversion of PdCl[subscript 2] with acetonitrile to give [Pd(MeCN)[subscript 4]]Cl[subscript 2] as a precursor is performed at 80 °C. The third part of the experiment is a three-step procedure that begins with deprotonation of [H[subscript 6]Br[subscript 3]L]Cl, followed by transfer of [Pd(MeCN)[subscript 4]]Cl[subscript 2] to the reaction flask, where the chelation of Pd(II)-precursor leads to the in situ species [Pd(MeCN)H[subscript 3]Br[subscript 3]L]. Addition of PPh[subscript 3] as the final reaction step yields [Pd(PPh[subscript 3])H[subscript 3]Br[subscript 3]L]. This sequence of experiments provides an excellent example of ligand and transition metal preparation and its subsequent complexation to form an oxidant-sensitive organometallic species. Undergraduate students get the opportunity to learn Schlenk techniques and to investigate [superscript 1]H NMR spectra of organic and organometallic compounds starting from relatively simple to more advanced spectra. The distinct result of the chemical shift of the [superscript 4]J[subscript P-H]-affected doublet mirrors the preparative success of the student and demonstrates the utility of [superscript 1]H NMR experiments.