One-pot palladium-catalyzed cross-coupling reaction of aryl iodides with stannylarsanes and stannylstibanes

The reaction of Ph3As and Ph3Sb with Na metal in liquid ammonia gives Ph2M- ions (M = As, Sb) that react with n-Bu3SnCl to afford n-Bu3Sn-MPh2 (1). The ammonia was allowed to evaporate, and toluene was added. The Pd-catalyzed cross-coupling reactions of these stannanes with aryl iodides afford functionalized triaryl-arsanes and triaryl-stibanes in high yields in a one-pot procedure (80-99%). The use of the commercially available, air-stable, and inexpensive Ph3M as the initial reagent and the one-pot process make this method a useful approach. This is the first report on the synthesis of 1 and the exploration of its chemistry.