تفاعل #1095841

ord-f5149a68d27c46f0882d718c622b61aa

معادلة التفاعل

Ic1ccc2[nH]c3ccccc3c2c1
compound 1
Ic1ccc2[nH]c3ccccc3c2c1
3-Iodocarbazole
C=CC#N
acrylonitrile
c1ccc(P(c2ccccc2)c2ccccc2)cc1
triphenylphosphine
CCN(CC)CC
triethylamine
N#CC=Cc1ccc2[nH]c3ccccc3c2c1
compound 2
المردود 18.0%
N#CC=Cc1ccc2[nH]c3ccccc3c2c1
3-Cyanovinylcarbazole
المردود 18.0%
Ic1ccc2[nH]c3ccccc3c2c1
compound 1
المردود 37.0%
Ic1ccc2[nH]c3ccccc3c2c1
3-Iodocarbazole
المردود 37.0%

المذيبات

ظروف التفاعل

درجة الحرارة
75°CELSIUS
الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

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

الإجراء التجريبي

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.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US07972792B2uspto-grants-2011_07