910467-59-3

16116-78-2

17573-94-3

910467-59-3

GENERAL METHOD: N-(4-(ethynyl)phenyl)carbazole (5a, 0.53 g, 2.0 mmol), 4-{2-(trimethylsilyl)ethynyl}-1-bromobenzene (0.76 g, 3.0 mmol), Cl2Pd(PPh3)2 (0.084 g, 0.12 mmol), PPh3 (0.052 g, 0.20 mmol) , CuI (0.038 g, 0.20 mmol) and Et3N (20 mL) were added sequentially to the flask. The reaction mixture was stirred at 100 °C for 15 hours. After completion of the reaction, the precipitate was separated by filtration under atmospheric pressure and the filtrate was poured into saturated aqueous NH4Cl solution (20 mL). The aqueous phase was extracted three times with ethyl acetate (20 mL) and the combined organic layers were washed once with brine. The organic layer was dried over anhydrous Na2SO4 and filtered, and the filtrate was concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (eluent: hexane/CH2Cl2 = 5/1) to afford the white solid product 6a (0.48 g, 1.1 mmol) in 55% yield.