Synthesis of diarylmethane derivatives from Stille cross-coupling reactions of benzylic halides

A catalyst precursor prepared in situ from palladium acetate and a phosphine ligand was used for the Stille cross-coupling reaction of benzylic bromides and chlorides with aryltributyltin analogues. The reactions were performed at 80 °C using dppf as ligand in the presence of KF, or more conveniently using PPh3 in the absence of base, furnishing diarylmethane derivatives in high yields (86-99%). Using Pd(OAc)2/PPh3 as catalyst precursor competitive Stille and Suzuki cross-coupling reactions with benzyl chloride showed that in the absence of base or in the presence of KF the Stille product is the majority product, and only the Suzuki product was obtained in the presence of KOH as base.