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A tridentate <i>bis</i>-NHC Pd complex, based on caffeine, was studied for its catalytic activity. This complex displayed a high catalytic activity in the Suzuki–Miyaura and Mizoroki–Heck cross-coupling reactions of aryl halides. The Sonogashira cross-coupling was also investigated but reveals a fast plateauing of the reaction. Aryl iodides as well as aryl bromides react when equipped with either electron-donating or electron-withdrawing substituents. Aryl chlorides, which contained electron-withdrawing groups, were also reactive under the applied conditions.