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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Bibliographic Details
Published inORGANIC CHEMISTRY FRONTIERS Vol. 6; no. 14; pp. 2392 - 2397
Main Authors Dou, Gui-Yuan, Jiang, Yang-Ye, Xu, Kun, Zeng, Cheng-Chu
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 2019
Royal Society of Chemistry
Subjects
Chemistry
Chemistry, Organic
Electrochemistry
Electrolysis
Electrolytes
Ions
Organic chemistry
Physical Sciences
Science & Technology
FUNCTIONALIZATION
DIFUNCTIONALIZATION
ALKENES
STYRENES
HETEROARENES
N-BU4NI
CASCADE
CATALYST
C-H TRIFLUOROMETHYLATION
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Summary: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.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 14
ISSN:2052-4129
2052-4110
2052-4110
DOI:10.1039/c9qo00552h