The general procedure for the synthesis of (4-hydroxyphenylacetylene)trimethylsilane from 4-iodophenol and trimethylsilylacetylene was as follows: 4-iodophenol (2 g, 9.09 mmol, 1 equiv) was dissolved in 20 mL of anhydrous toluene. To this solution was sequentially added PdCl2(PPh3)2 (191.4 mg, 0.27 mmol, 0.03 eq.), copper(I) iodide (172.8 mg, 0.909 mmol, 0.1 eq.), N,N-diisopropylethylamine (1.58 mL, 9.09 mmol, 1 eq.), followed by trimethylsilylacetylene (1.28 mL. 9.09 mmol, 1 equiv). The reaction mixture was stirred at room temperature for 24 hours. Upon completion of the reaction, the solvent was removed by evaporation and the residue was purified by column chromatography (eluent: EtOAc/hexane = 1:10) to afford the target product (4-hydroxyphenylacetylene)trimethylsilane (1.73 g, quantitative yield) as a brown oil. The structure of the product was confirmed by 1H-NMR (CDCl3, 500 MHz) and 13C-NMR (CDCl3, 75 MHz): 1H-NMR δ 7.37 (2H, d, J = 8.8 Hz, Ar-H), 6.76 (2H, d, J = 8.8 Hz, Ar-H), 4.92 (1H, brs, Ar-OH), 0.24 (9H , s, -Si(CH3)3); 13C-NMR δ 155.76, 133.69, 115.49, 115.31, 105.02, 92.50, 0.05.
