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...
Saved in:
Published in | Chemical communications (Cambridge, England) Vol. 56; no. 44; pp. 595 - 598 |
---|---|
Main Authors | , , , , |
Format | Journal Article |
Language | English |
Published |
CAMBRIDGE
Royal Soc Chemistry
04.06.2020
|
Subjects | |
Online Access | Get full text |
Cover
Loading…
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 |