A highly efficient and reusable palladium(II)/cationic 2,2′-bipyridyl-catalyzed stille coupling in water

Article abstract of DOI:10.3390/molecules21091205

A water-soluble PdCl₂ (NH₃ )₂ /cationic 2,2′ -bipyridyl system was found to be a highly efficient catalyst for Stille coupling of aryl iodides and bromides with organostannanes. The coupling reaction was conducted at 110^°C in water, under aerobic conditions, in the presence of NaHCO₃ as a base to afford corresponding Stille coupling products in good to high yields. When aryltributylstannanes were employed, the reactions proceeded smoothly under a very low catalyst loading (as little as 0.0001 mol %). After simple extraction, the residual aqueous phase could be reused in subsequent runs, making this Stille coupling economical. In the case of tetramethylstannane, however, a greater catalyst loading (1 mol %) and the use of tetraethylammonium iodide as a phase-transfer agent were required in order to obtain satisfactory yields.