The general procedure for the synthesis of 9-phenyl-9H-carbazole-3-boronic acid pinacol ester from 3-bromo-N-phenylcarbazole and bis(pinacolato)diboron (1.2 eq.), potassium acetate (1.5 eq.), and PdCl2 (dppf) (0.02 eq.) was carried out by dissolving halogenated arylenes (1.0 eq.), bis(pinacolato)diboron (1.2 eq.), potassium acetate (1.5 eq.) and PdCl2 (dppf) (0.02 eq.), protected by nitrogen, in anhydrous 1,4- dioxane (20 mL) and the reaction was refluxed overnight. After completion of the reaction, the reaction was cooled to room temperature, the reaction mixture was poured into water and extracted with dichloromethane. The organic layers were combined, washed with brine and dried over anhydrous magnesium sulfate. The solvent was removed by concentration under reduced pressure and the crude product was purified by silica gel column chromatography, eluting with a solvent mixture of dichloromethane and hexane to give the pure product 9-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole (3). Specific example: compound 3 (4.1 g, 88.4% yield) was obtained using 3-bromo-9-phenyl-9H-carbazole (4 g, 12.4 mmol), bis(pinacolato)diboron (3.79 g, 14.9 mmol), potassium acetate (1.9 g, 18.6 mmol) and PdCl2 (dppf) (0.14 g, 0.02 mmol) , a white solid with a melting point of 160°C.
