反应 #955950

反应方程式

trimethylsilyl-acetylene

3

5,5′-dibromo-2,2′-bipyridine

→

4

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

溶剂

THF

反应条件

后处理

1. 1
   workup.STIRRINGIt was stirred together with activated carbon for 20 minutes
2. 2
   过滤filtered over celite
3. 3
   其他Then the solvent was removed under reduced pressure
4. 4
   其他sonicated for 15 minutes
5. 5
   过滤filtered over celite
6. 6
   其他again yielding an orange solution
7. 7
   其他The solvent was removed under reduced pressure
8. 8
   其他the residue was purified by flash column chromatography on silica (eluent: CH2Cl2)

实验过程

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).

来源