Reaktion #955950

Reaktionsgleichung

trimethylsilyl-acetylene

3

5,5′-dibromo-2,2′-bipyridine

→

4

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

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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).

Quelle