Water → Bis(tributylstannyl)acetylene

A mixture of 48.8 g (0.150 Mol) of tri-n-butyl-tin chloride and 20.7 g (0.225 Mol) of lithium acetylide ethylenediamine complex in 300 mL of anhydrous THF was heated at reflux under argon for 24 h, cooled and treated with 200 mL of water. The layers were separated and the THF phase was suction-filtered through Celite with a 150 mL THF wash to afford a clear solution. This solution was washed with water (3×200 mL), saturated aqueous sodium bicarbonate (2×100 mL), 5% HCl (2×100 mL), and dried over anhydrous sodium sulfate. Removal of the solvent gave 40.2 g (88%) of the bis(tri-n-butylstannyl)ethyne as a colorless liquid. A mixture of 42.0 g (120 mMol) of 4-bromofluorobenzene, 30.2 g (50 mMol) of bis(tri-n-butylstannyl)acetylene and 2.5 g (2.24 mMol) of tetrakis(triphenylphosphine)palladium[0] under an argon atmosphere was dissolved in 200 mL of dry THF. The reaction mixture was refluxed under an argon atmosphere for 60 h. The solution was cooled to room temperature and subsequent cooling in a refrigerator overnight yielded 11.2 g (67%). The reaction was run at double the scale mentioned above and gave similar yields without any complication in the work-up procedure.