تفاعل #955972

معادلة التفاعل

4-aminobiphenyl

4-bromo-1,1′:3′,1″-terphenyl

sodium tert-butoxide

→

white solid

المردود 74.3%

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

المردود 74.3%

المذيبات

toluene

toluene

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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.

المصدر