Reacción #11285

Ecuación de reacción

4-Bromo-N,N-diphenylaniline

2-[9,9-dioctyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-fluoren-2-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

sodium carbonate

toluene

→

4-[9,9-dioctyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-fluoren-2-yl]-N,N-diphenylaniline

Disolventes

acetone

toluene hexane

water

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThis was purged with a stream of nitrogen for about 30 min
2. 2
   OtroUnder a nitrogen purge
3. 3
   TemperaturaThe reaction mixture was then refluxed for 16 hrs
4. 4
   OtroThe organic layer was separated
5. 5
   Lavadowashed with water
6. 6
   SecadoDrying of the organic layer over Na2SO4 and evaporation of the solvent
7. 7
   Otrogave a light yellow solid
8. 8
   Temperaturato reflux
9. 9
   FiltraciónFiltration of the solid and concentration of the filtrate
10. 10
    Otrogave a solid

Procedimiento

4-Bromo-N,N-diphenylaniline (19.44 g, 60 mmole, 1 equiv), 2-[9,9-dioctyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-fluoren-2-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (76.9 g, 120 mmole, 2 equiv), Aliquat™ 336 (tricaprylylmethylammonium chloride) (6 g, 15 mmole, 0.25 equiv) and 2M sodium carbonate solution (75 mL, 150 mmole, 2.5 equiv) were added to 600 mL of toluene. This was purged with a stream of nitrogen for about 30 min. Under a nitrogen purge, tetrakis(triphenylphosphine palladium (0) (348 mg, 0.30 mmole, 0.005 equiv) was added. The reaction mixture was then refluxed for 16 hrs. The reaction was cooled to room temperature and water added. The organic layer was separated and washed with water followed by brine. Drying of the organic layer over Na2SO4 and evaporation of the solvent gave a light yellow solid. This was suspended in acetone and the mixture brought to reflux and then allowed to stand at room temperature overnight. Filtration of the solid and concentration of the filtrate gave a solid that was subjected to column chromatography (toluene:hexane 3:7) to give 4-[9,9-dioctyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-fluoren-2-yl]-N,N-diphenylaniline.

Fuente