The selective electrochemical fluorination of S-alkyl benzothioate and its derivatives
We herein report that the regioselective anodic fluorination of S-alkyl benzothioate and its derivatives in various aprotic solvents using Et3N·nHF (n = 3–5) and Et4NF·nHF (n = 3–5) as supporting electrolyte and a fluorine source successfully provided the corresponding α-fluorinated products in mode...
| Main Authors: | , , , , , |
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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2018-02-01
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| Series: | Beilstein Journal of Organic Chemistry |
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| Online Access: | https://doi.org/10.3762/bjoc.14.27 |
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| author | Shunsuke Kuribayashi Tomoyuki Kurioka Shinsuke Inagi Ho-Jung Lu Biing-Jiun Uang Toshio Fuchigami |
| author_facet | Shunsuke Kuribayashi Tomoyuki Kurioka Shinsuke Inagi Ho-Jung Lu Biing-Jiun Uang Toshio Fuchigami |
| author_sort | Shunsuke Kuribayashi |
| collection | DOAJ |
| description | We herein report that the regioselective anodic fluorination of S-alkyl benzothioate and its derivatives in various aprotic solvents using Et3N·nHF (n = 3–5) and Et4NF·nHF (n = 3–5) as supporting electrolyte and a fluorine source successfully provided the corresponding α-fluorinated products in moderate yields. Dichloromethane containing Et4NF·4HF was found to be the most suitable combination as electrolytic solvent and supporting salt as well as fluorine source for the anodic fluorination. The electrochemical fluorination of cyclic benzothioates such as benzothiophenone was also achieved. |
| first_indexed | 2024-12-17T03:40:55Z |
| format | Article |
| id | doaj.art-2a13d13f3b404b9da06ca51d26d50b9e |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-12-17T03:40:55Z |
| publishDate | 2018-02-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-2a13d13f3b404b9da06ca51d26d50b9e2022-12-21T22:05:00ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972018-02-0114138939610.3762/bjoc.14.271860-5397-14-27The selective electrochemical fluorination of S-alkyl benzothioate and its derivativesShunsuke Kuribayashi0Tomoyuki Kurioka1Shinsuke Inagi2Ho-Jung Lu3Biing-Jiun Uang4Toshio Fuchigami5Department of Electronic Chemistry, Tokyo Institute of Technology, 4259 Nagatsuta-cho, Midori-ku, Yokohama 226-8502, JapanDepartment of Chemical Science and Engineering, School of Materials and Chemical Technology, Tokyo Institute of Technology, 4259 Nagatsuta-cho, Midori-ku, Yokohama 226-8502, JapanDepartment of Chemical Science and Engineering, School of Materials and Chemical Technology, Tokyo Institute of Technology, 4259 Nagatsuta-cho, Midori-ku, Yokohama 226-8502, JapanDepartment of Chemistry, National Tsing Hua University, 101, Sec 2, Kuang Fu Rd., Hsinchu 300, Taiwan, R.O.CDepartment of Chemistry, National Tsing Hua University, 101, Sec 2, Kuang Fu Rd., Hsinchu 300, Taiwan, R.O.CDepartment of Electronic Chemistry, Tokyo Institute of Technology, 4259 Nagatsuta-cho, Midori-ku, Yokohama 226-8502, JapanWe herein report that the regioselective anodic fluorination of S-alkyl benzothioate and its derivatives in various aprotic solvents using Et3N·nHF (n = 3–5) and Et4NF·nHF (n = 3–5) as supporting electrolyte and a fluorine source successfully provided the corresponding α-fluorinated products in moderate yields. Dichloromethane containing Et4NF·4HF was found to be the most suitable combination as electrolytic solvent and supporting salt as well as fluorine source for the anodic fluorination. The electrochemical fluorination of cyclic benzothioates such as benzothiophenone was also achieved.https://doi.org/10.3762/bjoc.14.27anodic cyclizationdiastereoselective fluorinationelectrosynthesisfluorobenzothiophenoneselective fluorination |
| spellingShingle | Shunsuke Kuribayashi Tomoyuki Kurioka Shinsuke Inagi Ho-Jung Lu Biing-Jiun Uang Toshio Fuchigami The selective electrochemical fluorination of S-alkyl benzothioate and its derivatives Beilstein Journal of Organic Chemistry anodic cyclization diastereoselective fluorination electrosynthesis fluorobenzothiophenone selective fluorination |
| title | The selective electrochemical fluorination of S-alkyl benzothioate and its derivatives |
| title_full | The selective electrochemical fluorination of S-alkyl benzothioate and its derivatives |
| title_fullStr | The selective electrochemical fluorination of S-alkyl benzothioate and its derivatives |
| title_full_unstemmed | The selective electrochemical fluorination of S-alkyl benzothioate and its derivatives |
| title_short | The selective electrochemical fluorination of S-alkyl benzothioate and its derivatives |
| title_sort | selective electrochemical fluorination of s alkyl benzothioate and its derivatives |
| topic | anodic cyclization diastereoselective fluorination electrosynthesis fluorobenzothiophenone selective fluorination |
| url | https://doi.org/10.3762/bjoc.14.27 |
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