反応 #955950

反応方程式

trimethylsilyl-acetylene

3

5,5′-dibromo-2,2′-bipyridine

→

4

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

溶媒

THF

反応条件

後処理

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

実験手順

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).

出典