期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 140, 期 19, 页码 6169-6175出版社
AMER CHEMICAL SOC
DOI: 10.1021/jacs.8b03077
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资金
- National Basic Research Program of China (973 Program) [2015CB931900]
- National Natural Science Foundation of China [21421002, 21472220, 21532008, 21602239, 21672001]
- Strategic Priority Research Program of the Chinese Academy of Sciences [XDB20020000]
The copper-assisted radical carbofluorination of unactivated alkenes with fluoride ions is described. With [Cu(L3)F-2]H2O (L3 = di(methoxycarbony1)-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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