Synthesis of potassium 4-(1-azol-1-yl)-2,3,5,6-tetrafluorophenyltrifluoroborates from K[C6F5BF3] and alkali metal azol-1-ides. The dramatic distinction in nucleophilicity of alkali metal azol-1-ides and dialkylamides Научная публикация
| Журнал |
Journal of Fluorine Chemistry
ISSN: 0022-1139 |
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| Вых. Данные | Год: 2013, Том: 156, Страницы: 290-297 Страниц : DOI: 10.1016/j.jfluchem.2013.07.011 | ||||
| Ключевые слова | Pentafluorophenyltrifluoroborate; N-nucleophile; Nucleophilic substitution; NMR spectroscopy | ||||
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Реферат:
Nucleophilic substitution of fluorine atom in K[C6F5BF3] with alkali metal azol-1-ides in polar aprotic solvent (DMF, DMSO) at 60-130 degrees C gives potassium 4-(azol-1-yl)-2,3,5,6-tetrafluorophenyltrifluorborates, K[4-AzC(6)F(4)BF(3)] (AzH = pyrrole, pyrazole, imidazole, indole, and benzimidazole). Unexpectedly, diethylamine and morpholine do not react with K[C6F5BF3] under the same conditions while pentafluorobenzene and R2NC6F4H form at 150 degrees C. Reaction of K[C6F5BF3] with Na[NR2] in diglyme or DMSO proceeds similar way. The assumed reason is the relatively low nucleophilicity of both secondary amines and alkali metal dialkylamides which results in destructive by-reaction with K[C6F5BF3] rather than in its aminodefluorination. This is confirmed by the competitive nucleophilic aminodefluorination of a model substrate, C6F5Ph, with sodium indolide/sodium morpholinide. (C) 2013 Elsevier B.V. All rights reserved.
Библиографическая ссылка:
Shabalin A.Y.
, Adonin N.Y.
, Bardin V.V.
, Taran O.P.
, Ayusheev A.B.
, Parmon V.N.
Synthesis of potassium 4-(1-azol-1-yl)-2,3,5,6-tetrafluorophenyltrifluoroborates from K[C6F5BF3] and alkali metal azol-1-ides. The dramatic distinction in nucleophilicity of alkali metal azol-1-ides and dialkylamides
Journal of Fluorine Chemistry. 2013. V.156. P.290-297. DOI: 10.1016/j.jfluchem.2013.07.011 WOS Scopus РИНЦ OpenAlex
Synthesis of potassium 4-(1-azol-1-yl)-2,3,5,6-tetrafluorophenyltrifluoroborates from K[C6F5BF3] and alkali metal azol-1-ides. The dramatic distinction in nucleophilicity of alkali metal azol-1-ides and dialkylamides
Journal of Fluorine Chemistry. 2013. V.156. P.290-297. DOI: 10.1016/j.jfluchem.2013.07.011 WOS Scopus РИНЦ OpenAlex
Даты:
| Опубликована в печати: | 1 дек. 2013 г. |
Идентификаторы БД:
| Web of science: | WOS:000329257000046 |
| Scopus: | 2-s2.0-84889094417 |
| РИНЦ: | 21464698 |
| OpenAlex: | W1973832952 |