A series of palladium pincer complexes supported by ( i Pr2P-C6H4)2CH2 (PC­(sp3)­H2P = bis­(2-(diisopropylphosphanyl)­phenyl)­methane) was isolated and characterized. Different modes of C–H activation were observed for [{PC­(sp3)­H2P}­PdX2] (X = Cl, OTf, Me, OAc). The thermal treatment of [{PC­(sp3)­H2P}­PdX2] (X = Cl, OTf) induced a backbone C–H bond activation to generate the respective [{PC­(sp3)­HP}­PdX] complex, while under similar reaction conditions [{PC­(sp3)­H2P}­PdMe2] underwent a C–C reductive elimination that led to the formation of a Pd(0) dimer, [{PC­(sp3)­H2P}­Pd]2. For the analogous diacetate complex [{PC­(sp3)­H2P}­Pd­(OAc)2], the C–H activation occurred at the phosphine isopropyl methine group to generate a palladacycle.