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

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Abstract

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.

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

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Article information


Submitted
20 Mar 2020
Accepted
09 Apr 2020
First published
16 Apr 2020

Chem. Commun., 2020, Advance Article
Article type
Communication

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

M. Artault, N. Mokhtari, T. Cantin, A. Martin-Mingot and S. Thibaudeau, Chem. Commun., 2020, Advance Article , DOI: 10.1039/D0CC02081H

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