Reacción #955972

Ecuación de reacción

4-aminobiphenyl

4-bromo-1,1′:3′,1″-terphenyl

sodium tert-butoxide

→

white solid

Rendimiento 74.3%

N-([1,1′-biphenyl]-4-yl)-[1,1′:3′,1″-terphenyl]-4-amine

Rendimiento 74.3%

Disolventes

toluene

toluene

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONThe catalyst solution was added to the reaction mixture
2. 2
   workup.STIRRINGstirred for 2 minutes
3. 3
   OtroFlask was capped
4. 4
   workup.WAITleft
5. 5
   workup.STIRRINGto stir in the drybox overnight at room temperature
6. 6
   OtroNext day, reaction mixture
7. 7
   Filtraciónfiltered through a one-inch plug of silica gel
8. 8
   Lavadowashing with 500 ml of dichloromethane
9. 9
   OtroRemoval of volatiles under reduced pressure
10. 10
    Otrogave a yellow solid
11. 11
    OtroCrude product was purified by trituration with diethyl ether

Procedimiento

In a drybox, 4-aminobiphenyl (0.542 g) and 4-bromo-1,1′:3′,1″-terphenyl (0.89 g) were combined in a round-bottom flask and dissolved in 10 ml of dry toluene. Tris(tert-butyl)phosphine (0.022 g, 0.11 mmol) and tris(dibenzylideneacetone) dipalladium(0) (0.05 g, 0.055 mmol) were dissolved in 10 ml of dry toluene and stirred for 5 minutes. The catalyst solution was added to the reaction mixture, stirred for 2 minutes and was followed by sodium tert-butoxide (0.32 g, 3.3 mmol). Flask was capped and left to stir in the drybox overnight at room temperature. Next day, reaction mixture was taken out of the box and filtered through a one-inch plug of silica gel topped with celite, washing with 500 ml of dichloromethane. Removal of volatiles under reduced pressure gave a yellow solid. Crude product was purified by trituration with diethyl ether to give 0.85 g (73%) of a white solid. Structure was confirmed by 1H NMR spectroscopy.

Fuente