Abstract
We have developed a novel electrolytic system for anodic oxidation of organic compounds based on the cation exchange reaction between potassium tetrafluoroborate (KBF4) and solid-supported acids. It was clarified by cyclic voltammetry as well as preparative electrolyses that hydrogen tetrafluoroborate (HBF4) derived from the cation exchange reaction acts as a supporting electrolyte in MeCN. On the basis of the electrolytic system, anodic oxidation of 1,2,4-trimethoxybenzene was carried out to provide the corresponding homocoupling product in quantitative yield. Furthermore, anodic oxidation of benzyl alcohols having not only electron-donating but also electron-withdrawing groups at the para position was successfully achieved by optimizing the reaction conditions.
| Original language | English |
|---|---|
| Pages (from-to) | 305-308 |
| Number of pages | 4 |
| Journal | Electrochemistry Communications |
| Volume | 11 |
| Issue number | 2 |
| DOIs | |
| Publication status | Published - 2009 Feb |
| Externally published | Yes |
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Keywords
- Anodic oxidation
- Cation exchange reaction
- Potassium tetrafluoroborate
- Solid-supported acid
- Supporting electrolyte
ASJC Scopus subject areas
- Electrochemistry
Cite this
Anodic oxidation of organic compounds based on the cation exchange reaction between KBF4 and solid-supported acids. / Nakajima, Atsushi; Tajima, Toshiki.
In: Electrochemistry Communications, Vol. 11, No. 2, 02.2009, p. 305-308.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Anodic oxidation of organic compounds based on the cation exchange reaction between KBF4 and solid-supported acids
AU - Nakajima, Atsushi
AU - Tajima, Toshiki
PY - 2009/2
Y1 - 2009/2
N2 - We have developed a novel electrolytic system for anodic oxidation of organic compounds based on the cation exchange reaction between potassium tetrafluoroborate (KBF4) and solid-supported acids. It was clarified by cyclic voltammetry as well as preparative electrolyses that hydrogen tetrafluoroborate (HBF4) derived from the cation exchange reaction acts as a supporting electrolyte in MeCN. On the basis of the electrolytic system, anodic oxidation of 1,2,4-trimethoxybenzene was carried out to provide the corresponding homocoupling product in quantitative yield. Furthermore, anodic oxidation of benzyl alcohols having not only electron-donating but also electron-withdrawing groups at the para position was successfully achieved by optimizing the reaction conditions.
AB - We have developed a novel electrolytic system for anodic oxidation of organic compounds based on the cation exchange reaction between potassium tetrafluoroborate (KBF4) and solid-supported acids. It was clarified by cyclic voltammetry as well as preparative electrolyses that hydrogen tetrafluoroborate (HBF4) derived from the cation exchange reaction acts as a supporting electrolyte in MeCN. On the basis of the electrolytic system, anodic oxidation of 1,2,4-trimethoxybenzene was carried out to provide the corresponding homocoupling product in quantitative yield. Furthermore, anodic oxidation of benzyl alcohols having not only electron-donating but also electron-withdrawing groups at the para position was successfully achieved by optimizing the reaction conditions.
KW - Anodic oxidation
KW - Cation exchange reaction
KW - Potassium tetrafluoroborate
KW - Solid-supported acid
KW - Supporting electrolyte
UR - http://www.scopus.com/inward/record.url?scp=58549084765&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=58549084765&partnerID=8YFLogxK
U2 - 10.1016/j.elecom.2008.11.032
DO - 10.1016/j.elecom.2008.11.032
M3 - Article
AN - SCOPUS:58549084765
VL - 11
SP - 305
EP - 308
JO - Electrochemistry Communications
JF - Electrochemistry Communications
SN - 1388-2481
IS - 2
ER -