Superelectrophilic Csp-H bond fluorination of aliphatic amines in superacid: the striking role of ammonium-carbenium dications

The superacid-promoted electrophilic Csp 3 -H bond activation of aliphatic amines generates superelectrophilic species that can be subsequently fluorinated. Demonstrated by low-temperature in situ NMR experiments, the ammonium-carbenium dications, crucial for this reaction, can also react with C-H b...

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Published inChemical communications (Cambridge, England) Vol. 56; no. 44; pp. 595 - 598
Main Authors Artault, M, Mokhtari, N, Cantin, T, Martin-Mingot, A, Thibaudeau, S
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 04.06.2020
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
FUNCTIONALIZATION
ELECTROPHILIC FLUORINATION
CARBOCATIONS
ELEMENTAL FLUORINE
SELECTIVE FLUORINATION
ION FORMATION
EXPLORATION
CHEMISTRY
MONOFLUORINATION
C-H BONDS
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Summary:The superacid-promoted electrophilic Csp 3 -H bond activation of aliphatic amines generates superelectrophilic species that can be subsequently fluorinated. Demonstrated by low-temperature in situ NMR experiments, the ammonium-carbenium dications, crucial for this reaction, can also react with C-H bonds opening future synthesis perspectives for this mode of activation. Superelectrophilic activation in a superacid, HF/SbF 5 , allows for C-H bond fluorination and functionalization of aliphatic amines.
Bibliography:Electronic supplementary information (ESI) available. See DOI
10.1039/d0cc02081h
ISSN:1359-7345
1364-548X
DOI:10.1039/d0cc02081h