Réaction #955950

Équation de réaction

trimethylsilyl-acetylene

3

5,5′-dibromo-2,2′-bipyridine

→

4

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

Solvants

THF

Conditions de réaction

Traitement

1. 1
   workup.STIRRINGIt was stirred together with activated carbon for 20 minutes
2. 2
   Filtrationfiltered over celite
3. 3
   AutreThen the solvent was removed under reduced pressure
4. 4
   Autresonicated for 15 minutes
5. 5
   Filtrationfiltered over celite
6. 6
   Autreagain yielding an orange solution
7. 7
   AutreThe solvent was removed under reduced pressure
8. 8
   Autrethe residue was purified by flash column chromatography on silica (eluent: CH2Cl2)

Mode opératoire

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).

Source