Synthesis of alpha-CF3 and alpha-CF2H amines via the aminofluorination of fluorinated alkenes

A novel synthesis of alpha-CF3 and alpha-CF2H amines via the aminofluorination of gem-difluoroalkenes and mono-fluoroalkenes, respectively, is reported. The method employs Selectfluor as an electrophilic fluorine source and acetonitrile as a nitrogen source. Mechanistic studies revealed a single-ele...

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Published inChemical communications (Cambridge, England) Vol. 54; no. 46; pp. 5907 - 5910
Main Authors Yang, Ling, Fan, Wen-Xin, Lin, E., Tan, Dong-Hang, Li, Qingjiang, Wang, Honggen
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 2018
Royal Society of Chemistry
Subjects
Acetonitrile
Alkenes
Amines
Chemistry
Chemistry, Multidisciplinary
Fluorination
Fluorine
Functional groups
Oxidation
Physical Sciences
Science & Technology
Synthesis
ARYL BROMIDES
CROSS-COUPLING REACTIONS
COPPER-MEDIATED DIFLUOROMETHYLATION
GEM-DIFLUOROALKENES
STEREOSELECTIVE-SYNTHESIS
SILYL ETHERS
RITTER REACTION
METAL-FREE
GRIGNARD-REAGENTS
DIFLUOROENOL SILYL
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Summary:A novel synthesis of alpha-CF3 and alpha-CF2H amines via the aminofluorination of gem-difluoroalkenes and mono-fluoroalkenes, respectively, is reported. The method employs Selectfluor as an electrophilic fluorine source and acetonitrile as a nitrogen source. Mechanistic studies revealed a single-electron oxidation/fluorine-abstraction/Ritter-type amination pathway. The protocol allowed the synthesis of a broad range of fluorinated amines including those bearing quaternary carbon centers with good efficiency and functional group tolerance.
Bibliography:ObjectType-Article-1
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ISSN:1359-7345
1364-548X
DOI:10.1039/c8cc03364a