Reaction #955950

Reaction equation

trimethylsilyl-acetylene

3

5,5′-dibromo-2,2′-bipyridine

→

4

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

Solvents

THF

Conditions

Workup

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

Procedure

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