Synthesis of K[4-ROC6F4BF3] from potassium pentafluorophenyltrifluoroborate and O-nucleophiles Full article
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Journal of Fluorine Chemistry
ISSN: 0022-1139 |
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| Output data | Year: 2013, Volume: 149, Pages: 82-87 Pages count : DOI: 10.1016/j.jfluchem.2013.01.020 | ||||
| Tags | Pentafluorophenyltrifluoroborate; O-nucleophile; Nucleophilic substitution; NMR spectroscopy | ||||
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Abstract:
A new route to potassium polyfluoroaryltrifluoroborates, K[4-ROC6F4BF3], consisting in the nucleophilic alkoxydefluorination of K[C6F5BF3] with MOR (M = K, Na) in a polar aprotic solvent is suggested. Reaction of K[C6F5BF3] with KO-t-Bu proceeds smoothly at 25 degrees C in DME, but the attempted alkoxydefluorination of K[C6F5BF3] with other NaOR at 30 degrees C in DME failed. A series of K[4-ROC6F4BF3] (R approximate to Me, Et, Pr, i-Pr, Bu, PhCH2) is prepared using the corresponding sodium alkoxides in DMF at 130 degrees C in 80-90% isolated yield. Salt K[4-CH2=CHCH2OC6F4BF3] is prepared at 100 degrees C whereas at 130 degrees C formation of 2,3,5,6-C6F4HOCH2CH=CH2 occurs. Salt K[4-PhOC6F4BF3] is obtained in 82% yield using KOPh (2 equivalents) in DMSO at 130 degrees C. (C) 2013 Elsevier B.V. All rights reserved.
Cite:
Shabalin A.Y.
, Adonin N.Y.
, Bardin V.V.
, Prikhod'ko S.A.
, Timofeeva M.N.
, Bykova M.V.
, Parmon V.N.
Synthesis of K[4-ROC6F4BF3] from potassium pentafluorophenyltrifluoroborate and O-nucleophiles
Journal of Fluorine Chemistry. 2013. V.149. P.82-87. DOI: 10.1016/j.jfluchem.2013.01.020 WOS Scopus РИНЦ OpenAlex
Synthesis of K[4-ROC6F4BF3] from potassium pentafluorophenyltrifluoroborate and O-nucleophiles
Journal of Fluorine Chemistry. 2013. V.149. P.82-87. DOI: 10.1016/j.jfluchem.2013.01.020 WOS Scopus РИНЦ OpenAlex
Dates:
| Published print: | May 1, 2013 |
Identifiers:
| Web of science: | WOS:000317883600013 |
| Scopus: | 2-s2.0-84875428391 |
| Elibrary: | 20428290 |
| OpenAlex: | W2080025051 |