Abstract
Recent studies on electrochemical partial fluorination in ionic liquid fluoride salts are reviewed. At first, historical background and some problems of electrochemical fluorination in organic solvents are briefly mentioned. Solvent-free electrochemical fluorinations in ionic liquids are explained as follows. Ultrasonication was found to improve both the yield and current efficiency for electrochemical fluorination of α-phenylthioacetate, which is mainly attributable to marked mass transport promotion of the substrate and the suppression of anode passivation. Highly regioselective and efficient fluorination of cyclic ethers, lactones, and cyclic carbonate was achieved in Et4NF·4HF and Et3N·5HF. Selective fluorination of hardly oxidizable phthalide was realized using a combination of imidazolium and fluoride ionic liquids. The unique effect of imidazolium ionic liquids on electrochemical fluorodesulfurization of 3-phenylthiophthalide was explained. Reuse of ionic liquids for electrochemical fluorination is also possible.
| Original language | English |
|---|---|
| Pages (from-to) | 181-187 |
| Number of pages | 7 |
| Journal | Journal of Fluorine Chemistry |
| Volume | 126 |
| Issue number | 2 |
| DOIs | |
| Publication status | Published - 2005 Feb |
| Externally published | Yes |
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Keywords
- Anodic fluorination
- Fluorodesulfurization
- Ionic liquid
- Ultrasonication
ASJC Scopus subject areas
- Inorganic Chemistry
- Organic Chemistry
- Materials Chemistry
- Polymers and Plastics
Cite this
Highly selective electrochemical fluorination of organic compounds in ionic liquids. / Fuchigami, Toshio; Tajima, Toshiki.
In: Journal of Fluorine Chemistry, Vol. 126, No. 2, 02.2005, p. 181-187.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Highly selective electrochemical fluorination of organic compounds in ionic liquids
AU - Fuchigami, Toshio
AU - Tajima, Toshiki
PY - 2005/2
Y1 - 2005/2
N2 - Recent studies on electrochemical partial fluorination in ionic liquid fluoride salts are reviewed. At first, historical background and some problems of electrochemical fluorination in organic solvents are briefly mentioned. Solvent-free electrochemical fluorinations in ionic liquids are explained as follows. Ultrasonication was found to improve both the yield and current efficiency for electrochemical fluorination of α-phenylthioacetate, which is mainly attributable to marked mass transport promotion of the substrate and the suppression of anode passivation. Highly regioselective and efficient fluorination of cyclic ethers, lactones, and cyclic carbonate was achieved in Et4NF·4HF and Et3N·5HF. Selective fluorination of hardly oxidizable phthalide was realized using a combination of imidazolium and fluoride ionic liquids. The unique effect of imidazolium ionic liquids on electrochemical fluorodesulfurization of 3-phenylthiophthalide was explained. Reuse of ionic liquids for electrochemical fluorination is also possible.
AB - Recent studies on electrochemical partial fluorination in ionic liquid fluoride salts are reviewed. At first, historical background and some problems of electrochemical fluorination in organic solvents are briefly mentioned. Solvent-free electrochemical fluorinations in ionic liquids are explained as follows. Ultrasonication was found to improve both the yield and current efficiency for electrochemical fluorination of α-phenylthioacetate, which is mainly attributable to marked mass transport promotion of the substrate and the suppression of anode passivation. Highly regioselective and efficient fluorination of cyclic ethers, lactones, and cyclic carbonate was achieved in Et4NF·4HF and Et3N·5HF. Selective fluorination of hardly oxidizable phthalide was realized using a combination of imidazolium and fluoride ionic liquids. The unique effect of imidazolium ionic liquids on electrochemical fluorodesulfurization of 3-phenylthiophthalide was explained. Reuse of ionic liquids for electrochemical fluorination is also possible.
KW - Anodic fluorination
KW - Fluorodesulfurization
KW - Ionic liquid
KW - Ultrasonication
UR - http://www.scopus.com/inward/record.url?scp=17644410428&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=17644410428&partnerID=8YFLogxK
U2 - 10.1016/j.jfluchem.2004.11.003
DO - 10.1016/j.jfluchem.2004.11.003
M3 - Article
VL - 126
SP - 181
EP - 187
JO - Journal of Fluorine Chemistry
JF - Journal of Fluorine Chemistry
SN - 0022-1139
IS - 2
ER -