反应详情

9-BBN (0.5 M in THF, 38 mL, 19 mmol) was added dropwise into a solution of 9-allylcarbazole (29) (3.0 g, 14.5 mmol) in THF (10 mL) at 0° C. The mixture was stirred at room temperature for 15 minutes and then at 35° C. for 4 hours before transferring into a mixture of 1,3,5-tribromobenzene (19.5 g, 60.3 mmol), Pd(PPh3)4 (0.84 g, 0.72 mmol), K2CO3 (10.0 g, 72.4 mmol), H2O (15 mL) and THF (15 mL). The reaction mixture was stirred at 90° C. overnight, cooled to room temperature, and then extracted with chloroform. The organic extracts were combined, washed with water and dried over MgSO4. Upon evaporating off the solvent, the crude product was purified by column chromatography on silica gel with hexane/methlylene chloride 10:1 to 9:1 (v/v) as the eluent to yield 30 as a white crystals (5.4 g, 84%). 1H NMR (400 MHz, CDCl3, 298 K): 8.11-8.10 (d, 2H), 7.49-7.45 (m, 3H), 7.34-7.32 (m, 2H), 7.26-7.20 (m, 4H), 4.37-4.33 (t, 2H), 2.65-2.60 (d, J=7.6 Hz, 2H), 2.25-2.18 (m, 2H).

1. stirringThe reaction mixture was stirred at 90° C. overnight
2. temperaturecooled to room temperature
3. extractionextracted with chloroform
4. washwashed with water
5. dry with materialdried over MgSO4
6. customUpon evaporating off the solvent
7. customthe crude product was purified by column chromatography on silica gel with hexane/methlylene chloride 10:1 to 9:1 (v/v) as the eluent