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Nucleophilic fluoroalkylation of iminium salts |
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| Authors: | Vitalij V Levin Young-Hun Song Pavel A Belyakov Vladimir A Tartakovsky |
| Institution: | a N. D. Zelinsky Institute of Organic Chemistry, 119991 Moscow, Leninsky Prospect 47, Russia b Moscow Chemical Lyceum, 111033 Moscow, Tamozhennyj Proezd, 4, Russia c Korea Science Academy, 111 Baekyang Gwanmun Ro, Busanjin-Gu, Busan, Republic of Korea |
| Abstract: | Iminium cations generated by the coupling of aldehydes, N-trimethylsilylamines and TMSOTf or by the methylation of imines with MeOTf smoothly react with silanes of a general formula Me3SiRf (Rf = CF3, CCl2F, C6F5) to afford the corresponding tertiary amines having a fluorinated substituent. The key step, involving C-C bond formation, is promoted by NaOAc or KF in DMF as a solvent. |
| Keywords: | Iminium ions Imines Fluorinated silanes Lewis bases |
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