Reaction Steps
To a dry pressure Schlenk tube equipped with a magnetic stir bar was added 2′-(pyridin-2-yl)-9H-2,9′-bicarbazole (409 mg, 1.0 mmol, 1.0 eq), 2-chloro-4-phenylpyridine (228 mg, 1.2 mmol, 1.2 eq), Pd2(dba)3 (36 mg, 0.04 mmol, 0.04 eq), JohnPhos (48 mg, 0.16 mmol, 0.16 eq) and tBuONa (154 mg, 1.6 mmol, 1.6 eq). Then the tube was evacuated and back-filled with nitrogen, the evacuation and back-fill procedure was repeated twice. Then dry solvent toluene (4 mL) and dioxane (4 mL) were added under the protection of nitrogen. The tube was sealed and the mixture was stirred in an oil bath at a temperature of 95-105° C. for 2 days. Then the mixture was cooled to ambient temperature. The solvent was removed under reduced pressure and the residue was purified through column chromatography on silica gel using hexane and ethyl acetate (10:1-5:1-3:1) as an eluent to obtain the desired product, 9-(4-phenylpyridin-2-yl)-2′-(pyridin-2-yl)-9H-2,9′-bicarbazole Ligand N3NPh, as a brown solid (561 mg in 99.7% yield). 1H NMR (DMSO-d6, 400 MHz): δ 7.29-7.34 (m, 2H), 7.41-7.48 (m, 5H), 7.53-7.60 (m, 2H), 7.64 (dd, J=8.0, 1.2 Hz, 1H), 7.76 (d, J=4.8 Hz, 1H), 7.82-7.88 (m, 3H), 7.97 (d, J=8.0 Hz, 1H), 8.05 (d, J=8.4 Hz, 1H), 8.10 (s, 1H), 8.19 (s, 1H), 8.26 (s, 1H), 8.30 (d, J=7.6 Hz, 1H), 8.36 (d, J=8.4 Hz, 1H), 8.42 (d, J=8.0 Hz, 1H), 8.59-8.61 (m, 2H), 8.70 (d, J=5.6 Hz, 1H). 13C NMR (DMSO-d6, 100 MHz): δ 107.61, 109.87, 110.25, 111.57, 116.34, 118.65, 119.76, 119.97, 120.25, 120.35, 120.77, 120.81, 120.88, 121.48, 122.05, 122.39, 122.42, 123.07, 123.13, 123.38, 126.70, 126.98, 127.09, 129.16, 129.66, 134.83, 136.48, 136.74, 137.22, 139.79, 139.80, 141.25, 141.50, 149.46, 150.17, 150.40, 151.30, 156.16.
