Reacción #2045083

Ecuación de reacción

3-bromo-9H-carbazole

9-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole

K3PO4

→

9H,9′H-3,3′-bicarbazole

Rendimiento 73.1%

Disolventes

toluene

water

Condiciones de reacción

Tratamiento posterior

1. 1
   Extracciónthe reaction mixture was extracted with dichloromethane
2. 2
   Lavadowashed with brine
3. 3
   SecadoThe combined organic solutions were dried over Na2SO4
4. 4
   Filtraciónfiltered
5. 5
   Otrothe solvent was evaporated
6. 6
   Otroto yield a crude product, which
7. 7
   Otrowas recrystallized from DCM/hexane (1/1, v/v, 1200 mL)

Procedimiento

A mixture solution of 3-bromo-9H-carbazole (6.75 g, 27.4 mmol), 9-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole (12.15 g, 32.9 mmol), Pd2(dba)3 (0.251 g, 0.274 mmol), SPhos (0.450 g, 1.097 mmol) and K3PO4 (25.3 g, 110 mmol) in toluene (500 mL) and water (50 mL) was refluxed under nitrogen for 10 h. After cooling to room temperature, the reaction mixture was extracted with dichloromethane and washed with brine. The combined organic solutions were dried over Na2SO4, filtered, and the solvent was evaporated to yield a crude product, which was recrystallized from DCM/hexane (1/1, v/v, 1200 mL) to yield 9H,9′H-3,3′-bicarbazole (6.66 g, 59%) as a yellow solid.

Fuente