Br[C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][C:8](Br)=[CH:9][CH:10]=3)[N:5](CCCCCCCC)[C:4]=2[CH:3]=1.C1C2NC3C(=CC=CC=3)C=2C=CC=1B1OC(C)(C)C(C)(C)O1.C([O-])([O-])=O.[K+].[K+]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C1(C)C=CC=CC=1>[CH:3]1[C:4]2[NH:5][C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[C:12]=2[CH:13]=[CH:14][CH:2]=1A solution of 2,7-dibromo-9-octyl-9H-carbazole (220 mg, 0.5 mmol), 9H-carbazole-2-boronic acid pinacol ester (880 mg, 1.5 mmol) and benzyltriethylammonium chloride (50 mg) in a mixture of toluene (20 mL) and aqueous K2CO3 (2M, 8 mL) was degassed by three freeze-pump-thaw cycles. Pd(PPh3)4 (5 mg) was added under argon and degassed by three freeze-pump-thaw again. The mixture was refluxed for 24 h and the organic phase was separated and evaporated. The product was purified by column chromatography (hexane/THF, 4:2) and dried in vacuum. A 220 mg (71%) yield of trimer carbazole was obtained as a light brown powder. 1H NMR (THF-d8, 500 MHz): δ=10.33 (s, 2H), 8.15 (m, 4H), 8.07 (d, J=7.9, 2H), 7.82 (m, 4H), 7.6 (m, 4H), 7.43 (d, J=8.0, 2H), 7.34 (m, 2H), 7.15 (m, 2H), 4.56 (t, J=7.19, 2H), 1.99 (m, 2H), 1.29 (m, 10H), 0.83 (t, J=6.9, 3H). MALDI-TOF MS: m/z 609.33 (100%).
読み込み中…
