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JOURNAL ARTICLE
RESEARCH SUPPORT, NON-U.S. GOV'T
Radical Carbofluorination of Unactivated Alkenes with Fluoride Ions.
Journal of the American Chemical Society 2018 May 17
The copper-assisted radical carbofluorination of unactivated alkenes with fluoride ions is described. With [Cu(L3)F2 ]H2 O (L3 = 4,4'-di(methoxycarbonyl)-2,2'-bipyridine) as the fluorine source and [Ag(DMPhen)(MeCN)]BF4 (DMPhen = 2,9-dimethyl-1,10-phenanthroline) as the chloride scavenger, the reaction of unactivated alkenes with CCl4 in acetonitrile provided the corresponding carbofluorination products in satisfactory yields. The protocol exhibited a wide functional group compatibility and broad substrate scope and could be extended to the use of a variety of activated alkyl chlorides other than CCl4 . A copper-catalyzed fluorotrifluoromethylation of unactivated alkenes was then successfully developed with CsF as the fluorine source and Umemoto's reagent as the trifluoromethylating agent. A mechanism involving the fluorine atom transfer from Cu(II)-F complexes to alkyl radicals is proposed.
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