Pd-Catalyzed Cross-Coupling of Sb-Aryl Stibines with Halogenomethyl Arenes to Give Unsymmetirc Diarylmethanes

Herein, we describe a general method for the synthesis of unsymmetric diarylmethanes from (hetero)­aryl methyl halides and Sb-aryl stibines. This protocol shows a broad substrate scope and a good functional group tolerance. Drug molecules, including beclobrate 3al and bifemelane 3as, and drug derivatives, including celecoxib 3p, ibuprofen 3ao, and probenecid 3ap, were efficiently synthesized on a gram scale. The possible mechanism is proposed on the basis of the results of control experiments.