Reaction #1095841

Reaction equation

compound 1

3-Iodocarbazole

acrylonitrile

triphenylphosphine

triethylamine

→

compound 2

Yield 18.0%

3-Cyanovinylcarbazole

Yield 18.0%

compound 1

Yield 37.0%

3-Iodocarbazole

Yield 37.0%

Solvents

AcOEt

HexH

dioxane

dioxane

Conditions

Workup

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

Procedure

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