Reaction #1726664

Reaction equation

tri(tert-butyl)phosphine

9-(4′-bromobiphenyl-4-yl)-10-phenylanthracene

N,N′,N′-triphenylbenzidine

sodium tert-butoxide

→

light yellow solid

Yield 50.0%

N-[4′-(10-phenyl-9-anthryl)biphenyl-4-yl]-N,N′,N′-triphenyl-benzidine

Yield 50.0%

Solvents

toluene

toluene

Conditions

Workup

1. 1
   OtherInto a 50 mL three-neck flask were put
2. 2
   OtherAfter this mixture was degassed under reduced pressure
3. 3
   workup.STIRRINGThen, the mixture was stirred at 90° C. for 3 hours
4. 4
   FiltrationThe mixture was subjected to suction filtration
5. 5
   Otherto remove the solid
6. 6
   Filtrationthe obtained filtrate was subjected to suction filtration through Celite (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 531-16855), alumina, and Florisil (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 540-00135)
7. 7
   OtherA solid obtained by concentration of the filtrate
8. 8
   Otherwas recrystallized with toluene/hexane

Procedure

Into a 50 mL three-neck flask were put 1.1 g (2.2 mmol) of 9-(4′-bromobiphenyl-4-yl)-10-phenylanthracene, 0.93 g (2.2 mmol) of N,N′,N′-triphenylbenzidine (abbreviation: DPBA), and 1.0 g (10 mmol) of sodium tert-butoxide, and the atmosphere in the flask was replaced with nitrogen. Then, 15 mL of toluene and 0.10 mL of tri(tert-butyl)phosphine (10 wt % hexane solution) were added into this mixture. After this mixture was degassed under reduced pressure while being stirred, 58 mg (0.10 mmol) of bis(dibenzylideneacetone)palladium(0) was added thereto. Then, the mixture was stirred at 90° C. for 3 hours. After the stirring, about 20 mL of toluene was added into the mixture. The mixture was subjected to suction filtration to remove the solid, the obtained filtrate was subjected to suction filtration through Celite (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 531-16855), alumina, and Florisil (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 540-00135). A solid obtained by concentration of the filtrate was recrystallized with toluene/hexane to give 0.92 g of a light yellow solid, which was the object of the synthesis, in a yield of 50%.

Source