Réaction #1095841

Équation de réaction

compound 1

3-Iodocarbazole

acrylonitrile

triphenylphosphine

triethylamine

→

compound 2

Rendement 18.0%

3-Cyanovinylcarbazole

Rendement 18.0%

compound 1

Rendement 37.0%

3-Iodocarbazole

Rendement 37.0%

Solvants

AcOEt

HexH

dioxane

dioxane

Conditions de réaction

Traitement

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

Mode opératoire

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.

Source