Superelectrophilic Csp3–H bond fluorination of aliphatic amines in superacid: the striking role of ammonium–carbenium dications

The superacid-promoted electrophilic Csp3–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 bon...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2020-01, Vol.56 (44), p.5905-5908
Main Authors: Artault, M, Mokhtari, N, Cantin, T, Martin-Mingot, A, Thibaudeau, S
Format: Article
Language:English
Subjects:
Activation
Aliphatic amines
Fluorination
Hydrogen bonds
Low temperature
NMR
Nuclear magnetic resonance
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Summary:The superacid-promoted electrophilic Csp3–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.
ISSN:1359-7345
1364-548X
DOI:10.1039/d0cc02081h