| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1314957 | Journal of Fluorine Chemistry | 2011 | 4 Pages |
The interaction of 2-nitrocinnamates with silicon reagents Me3SiRf (Rf = CF3, C2F5, and C6F5) promoted either by sodium acetate in DMF or by tetrabutylammonium acetate in dichloromethane has been described. The reactions proceed as conjugate addition of fluorinated carbanion at the CC bond and afford 3-aryl-2-nitrobutanoates bearing a fluorinated substituent in good yields as diastereomeric mixtures in ratio from 1:1 to 1.6:1.
Graphical abstractNucleophilic addition of fluorinated carbanions to 2-nitrocinnamates using silicon reagents Me3SiRf (Rf = CF3, C2F5, and C6F5) is described.Figure optionsDownload full-size imageDownload as PowerPoint slideHighlights► Conjugate addition of fluorinated carbanion to 2-nitrocinnamates. ► Nucleophilic trifluoromethylation using the Ruppert–Prakash reagent. ► Fluorinated silanes are activated by acetate anion.
