Electrochemical Minisci-type trifluoromethylation of electron-deficient heterocycles mediated by bromide ions
An electrochemical methodology for the Minisci-type trifluoromethylation of electron-deficient heterocycles mediated by cheap and easily available bromide ions has been developed. By virtue of the in situ generated sulfonyl hypobromite intermediate, the CF3 radical can be regulated and controlled at...
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| Published in | ORGANIC CHEMISTRY FRONTIERS Vol. 6; no. 14; pp. 2392 - 2397 |
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| Main Authors | , , , |
| Format | Journal Article |
| Language | English |
| Published |
CAMBRIDGE
Royal Soc Chemistry
2019
Royal Society of Chemistry |
| Subjects | |
| Online Access | Get full text |
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| Abstract | An electrochemical methodology for the Minisci-type trifluoromethylation of electron-deficient heterocycles mediated by cheap and easily available bromide ions has been developed. By virtue of the in situ generated sulfonyl hypobromite intermediate, the CF3 radical can be regulated and controlled at a low concentration, thereby improving the reaction efficiency over direct electrolysis. Also, this indirect electrochemical process is performed in a beaker-type undivided cell under galvanostatic conditions, without using external expensive supporting electrolytes. This protocol provides an alternative electrochemical trifluoromethylation methodology for the late-stage functionalization of biologically important molecules. |
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| AbstractList | An electrochemical methodology for the Minisci-type trifluoromethylation of electron-deficient heterocycles mediated by cheap and easily available bromide ions has been developed. By virtue of the in situ generated sulfonyl hypobromite intermediate, the CF3 radical can be regulated and controlled at a low concentration, thereby improving the reaction efficiency over direct electrolysis. Also, this indirect electrochemical process is performed in a beaker-type undivided cell under galvanostatic conditions, without using external expensive supporting electrolytes. This protocol provides an alternative electrochemical trifluoromethylation methodology for the late-stage functionalization of biologically important molecules. |
| Author | Jiang, Yang-Ye Zeng, Cheng-Chu Xu, Kun Dou, Gui-Yuan |
| Author_xml | – sequence: 1 givenname: Gui-Yuan surname: Dou fullname: Dou, Gui-Yuan organization: Beijing Univ Technol, Coll Life Sci & Bioengn, Beijing Key Lab Environm & Viral Oncol, Beijing 100124, Peoples R China – sequence: 2 givenname: Yang-Ye surname: Jiang fullname: Jiang, Yang-Ye organization: Beijing Univ Technol, Coll Life Sci & Bioengn, Beijing Key Lab Environm & Viral Oncol, Beijing 100124, Peoples R China – sequence: 3 givenname: Kun surname: Xu fullname: Xu, Kun organization: Beijing Univ Technol, Coll Life Sci & Bioengn, Beijing Key Lab Environm & Viral Oncol, Beijing 100124, Peoples R China – sequence: 4 givenname: Cheng-Chu surname: Zeng fullname: Zeng, Cheng-Chu email: zengcc@bjut.edu.cn organization: Beijing Univ Technol, Coll Life Sci & Bioengn, Beijing Key Lab Environm & Viral Oncol, Beijing 100124, Peoples R China |
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| Keywords | FUNCTIONALIZATION DIFUNCTIONALIZATION ALKENES STYRENES HETEROARENES N-BU4NI CASCADE CATALYST C-H TRIFLUOROMETHYLATION |
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| Title | Electrochemical Minisci-type trifluoromethylation of electron-deficient heterocycles mediated by bromide ions |
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