تفاعل #955950

معادلة التفاعل

trimethylsilyl-acetylene

3

5,5′-dibromo-2,2′-bipyridine

→

4

5,5′-Bis((trimethylsilyl)ethynyl)-2,2′-bipyridine

المذيبات

THF

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGIt was stirred together with activated carbon for 20 minutes
2. 2
   ترشيحfiltered over celite
3. 3
   أخرىThen the solvent was removed under reduced pressure
4. 4
   أخرىsonicated for 15 minutes
5. 5
   ترشيحfiltered over celite
6. 6
   أخرىagain yielding an orange solution
7. 7
   أخرىThe solvent was removed under reduced pressure
8. 8
   أخرىthe residue was purified by flash column chromatography on silica (eluent: CH2Cl2)

الإجراء التجريبي

Under dry nitrogen atmosphere, successively trimethylsilyl-acetylene (619 mg, 6.30 mmol), [Pd(PPh3)2Cl2] (112 mg, 159 μmol), CuI (54.5 mg, 286 μmol) and DIPA (4 ml) were added to a stirred suspension of 3 (500 mg, 1.59 mmol) in 30 ml THF. While the mixture was stirred for 24 hours at room temperature, its color turned black. It was stirred together with activated carbon for 20 minutes and filtered over celite. Then the solvent was removed under reduced pressure, the residue was resuspended in hexane, sonicated for 15 minutes and filtered over celite again yielding an orange solution. The solvent was removed under reduced pressure and the residue was purified by flash column chromatography on silica (eluent: CH2Cl2) to yield 430 mg (1.23 mmol, 78%) of pure 4 as an off-white solid. 1H NMR (CDCl3, 250 MHz): δ=8.71 (s, 2H, bpy-H), 8.33 (d, 2H, JHH=8.3 Hz, bpy-H), 7.85 (d, 2H, JHH=7.8 Hz, bpy-H), 0.27 (s, 18H, Si(CH3)3).

المصدر