Reaktion #1095841

Reaktionsgleichung

compound 1

3-Iodocarbazole

acrylonitrile

triphenylphosphine

triethylamine

→

compound 2

Ausbeute 18.0%

3-Cyanovinylcarbazole

Ausbeute 18.0%

compound 1

Ausbeute 37.0%

3-Iodocarbazole

Ausbeute 37.0%

Lösungsmittel

AcOEt

HexH

dioxane

dioxane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe reaction solution was refluxed for 11.5 hours
2. 2
   Sonstigethe palladium powder was removed by cotton filtration
3. 3
   SonstigeThe product was purified by column chromatography (HexH:AcOEt=4:1)

Vorschrift

To a dioxane solution (10 mL) of triphenylphosphine (139 mg, 0.53 μmol), palladium acetate (40.0 mg, 0.18 μmol) and triethylamine (0.59 μL, 4.23 mmol) were sequentially added, and the mixture was stirred for 5 minutes at 75° C. A dioxane solution (15 mL) of compound 1 (1.03 g, 3.52 mmol) and acrylonitrile (0.46 μL, 7.04 mmol) were added, and the reaction solution was refluxed for 11.5 hours. The product was confirmed by TLC (HexH:AcOEt=4:1), and then the palladium powder was removed by cotton filtration. The product was purified by column chromatography (HexH:AcOEt=4:1), and compound 2 (0.14 g, 18%, trans:cis=97:3) was obtained as a white powder, while compound 1 (0.37 g, recovery rate 37%) was recovered as a white powder.

Quelle