Use of polymer-supported phenyltin for the creation of aryl–aryl or aryl–heteroaryl bonds via Stille cross-coupling reactions

An insoluble polymer-supported phenyltin reagent was successfully used in Stille cross-coupling reactions with aryl- and heteroaryl-halides. Cross-coupling products were isolated in good to high yields with very low contamination by tin and palladium residues after removal of the residual supported organotin halide. The regeneration and recyclability of the supported phenyltin reagent were also examined and proved to be possible, but required palladium cleaning of the grafted polymer to be efficient along 4 cycles when Pd(PPh3)4 was used as catalyst.