Bi-Catalyzed Trifluoromethylation of C(sp2)–H Bonds under Light
Journal of the American Chemical Society,
Journal Year:
2023,
Volume and Issue:
145(47), P. 25538 - 25544
Published: Nov. 14, 2023
We
disclose
a
Bi-catalyzed
C–H
trifluoromethylation
of
(hetero)arenes
using
CF3SO2Cl
under
light
irradiation.
The
catalytic
method
permits
the
direct
functionalization
various
heterocycles
bearing
distinct
functional
groups.
structural
and
computational
studies
suggest
that
process
occurs
through
an
open-shell
redox
manifold
at
bismuth,
comprising
three
unusual
elementary
steps
for
main
group
element.
cycle
starts
with
rapid
oxidative
addition
to
low-valent
Bi(I)
catalyst,
followed
by
light-induced
homolysis
Bi(III)–O
bond
generate
trifluoromethyl
radical
upon
extrusion
SO2,
is
closed
hydrogen-atom
transfer
Bi(II)
intermediate.
Language: Английский
Hydroxytrifluoroethylation and Trifluoroacetylation Reactions via SET Processes
Chemistry - A European Journal,
Journal Year:
2024,
Volume and Issue:
30(18)
Published: Jan. 6, 2024
Hydroxytrifluoroethyl
and
trifluoroacetyl
groups
are
of
utmost
importance
in
biologically
active
compounds,
but
methods
to
tether
these
motifs
organic
architectures
have
been
limited.
Typically,
the
preparation
compounds
relied
on
use
strong
bases
or
multistep
routes.
The
renaissance
radical
chemistry
photocatalytic,
transition
metal
mediated,
hydrogen
atom
transfer
(HAT)
processes
allowed
installation
medicinally
relevant
fluorinated
motifs.
This
review
provides
an
overview
available
for
direct
synthesis
hydroxytrifluoroethyl-
trifluoroacetyl-derived
governed
by
single-electron
processes.
Language: Английский
Harnessing photocatalytic and electrochemical approaches for C–H bond trifluoromethylation and fluoroalkylation
Organic Chemistry Frontiers,
Journal Year:
2023,
Volume and Issue:
11(3), P. 954 - 1014
Published: Dec. 14, 2023
The
review
summarises
various
photo-
and
electrochemical
strategies
for
trifluoromethylation
fluoroalkylation
of
different
C(sp
3
)–H,
2
C(sp)–H
bonds
in
several
classes
organic
molecules.
Language: Английский
New Opportunities to Access Fluorinated Molecules Using Organophotoredox Catalysis via C(sp3)–F Bond Cleavage
JACS Au,
Journal Year:
2025,
Volume and Issue:
5(2), P. 466 - 485
Published: Feb. 7, 2025
Fluorinated
molecules
are
of
paramount
importance
because
their
unique
properties.
As
a
result,
the
search
for
innovative
approaches
to
synthesis
this
class
compounds
has
been
relentless
over
years.
Among
these,
combination
photocatalysis
and
organofluorine
chemistry
turned
out
be
an
effective
partnership
access
unattainable
fluorinated
molecules.
This
Perspective
provides
overview
recent
advances
in
synthesizing
via
organophotoredox-catalyzed
defluorination
process
from
trifluoromethylated
compounds.
It
encompasses
preparation
difluoromethylated
(hetero)arenes,
amides,
esters
as
well
gem-difluoroalkene
derivatives
using
C(sp3)–F
bond
activation
or
β-fragmentation.
will
highlight
remaining
challenges
discuss
future
research
opportunities.
Language: Английский
Direct arene trifluoromethylation enabled by promiscuous activity of fungal laccase
Yi Ling Goh,
No information about this author
Shi Yang Preston Long,
No information about this author
Mun Fei Eddy Wong
No information about this author
et al.
Organic & Biomolecular Chemistry,
Journal Year:
2023,
Volume and Issue:
21(45), P. 8975 - 8978
Published: Jan. 1, 2023
Laccase
from
Trametes
versicolor
was
found
to
oxidize
non-phenolic
arenes
and
enable
the
trifluoromethylation
of
in
presence
situ
generated
CF3
radicals
at
a
catalyst
loading
as
low
0.0034%.
The
biocatalytic
proceeded
under
mild
conditions
could
increase
yield
by
up
12
fold,
compared
control.
Language: Английский
Difluoromethoxide Is a Strong Leaving Group in the Photoredox Deoxyradiofluorination of 2-Phenylpyridines
Meijuan Jiang,
No information about this author
Nicholas R. Ellin,
No information about this author
Sanjay Telu
No information about this author
et al.
The Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
89(18), P. 13768 - 13773
Published: Sept. 11, 2024
A
2-phenyl-3-difluoromethoxy-pyridinyl
moiety
features
in
potent
phosphodiesterase
4D
inhibitors
that
are
considered
to
be
candidate
radiotracers
for
positron
emission
tomography
if
they
labeled
with
fluorine-18.
Fluorine-18
could
installed
as
desired
at
the
3'-phenyl
position
acridinium-mediated
photoredox
radiodeoxyfluorination
homologues
bearing
variously
substituted
3'-aryloxy
groups.
However,
a
distal
3-difluoromethoxide
(-OCHF
Language: Английский
Tandem decarboxylation/fluorination of N-acetylanthranilic acids by iridium complexes
Tomohiko Shirai,
No information about this author
Tomokazu Yamasaki
No information about this author
Journal of Fluorine Chemistry,
Journal Year:
2024,
Volume and Issue:
274, P. 110260 - 110260
Published: Feb. 1, 2024
Language: Английский
3-(4-Fluorophenyl)-1-(1-(4-fluorophenyl)-3,3,3-trifluoroprop-1-en-1-yl)-5-fluoro-1H-pyrazole
Molbank,
Journal Year:
2023,
Volume and Issue:
2023(2), P. M1620 - M1620
Published: April 13, 2023
In
this
work,
the
title
compound
was
synthesized
via
visible-light-induced
radical
denitrogenative
trifluoromethylation
of
corresponding
vinyl
azide
followed
by
Cs2CO3-mediated
defluorinative
cyclization
resultant
azine.
The
widely
available
sodium
trifluoromethanesulfinate
is
used
as
a
precursor
CF3
radicals,
while
graphitic
carbon
nitride
(g-C3N4)
employed
an
environmentally
friendly,
cheap,
and
efficient
heterogeneous
photocatalyst.
structure
established
1H,
13C,
19F-NMR,
IR
spectroscopy,
mass-spectrometry.
Language: Английский