The selective cross coupling of benzylic chlorides with aryl Grignard reagents has been achieved by using catalytic amounts of FeCl2 and electronically tuned ortho-phenylenebisphosphine ligands. Although electron-deficient ligands promoted the reductive homocoupling of benzylic halides, electron-rich ligands effectively promoted the desired cross-coupling reaction to afford the corresponding diarylmethanes in good to excellent yields.