Angewandte Chemie,
Год журнала:
2024,
Номер
136(27)
Опубликована: Апрель 24, 2024
Abstract
Positron
emission
tomography
(PET)
is
becoming
increasingly
important
in
nuclear
medicine
and
drug
discovery.
To
date,
the
development
of
many
potential
PET
tracers
hampered
by
lack
suitable
synthetic
pathways
for
their
preparation.
This
particularly
true
highly
desired
radiolabeling
compounds
bearing
[
18
F]CF
3
‐groups.
For
instance,
S(O)
n
CF
‐groups
(
=0,
1,
2)
serve
as
structural
motif
a
range
biologically
active
compounds,
but
radiosynthesis
remains
largely
unprecedented
(for
=1,
2).
Herein,
we
describe
general
methods
F‐labeled
aryl
trifluoromethyl
sulfones,
‐sulfoxides,
‐sulfides.
All
three
are
operationally
straightforward,
start
from
widely
available
precursors,
i.e.,
sulfonyl
fluorides
thiophenols,
make
use
recently
established
F]Ruppert‐Prakash
reagent.
Further,
syntheses
display
good
functional
group
tolerance
demonstrated
F‐labeling
more
than
40
compounds.
The
applicability
new
method
bioactive
molecules,
optionally
to
be
used
tracers.
In
broader
context,
this
work
presents
substantial
expansion
chemical
space
radiofluorinated
motifs
The Journal of Organic Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Фев. 28, 2025
An
effective
trifluoromethyl
radical
addition
to
the
thiocarbonyl
of
thioamide
derivatives
is
described,
which
produces
various
trifluoromethylthiolated
N-heterocycles
such
as
6-(trifluoromethylthio)phenanthridine,
2-(trifluoromethylthio)indole,
and
2-(trifluoromethylthio)benzothiazole
under
visible-light
irradiation.
The
process
features
advantages
mild
reaction
conditions,
a
cheap
easily
available
source
(CF3Br),
green
energy,
well
broad
substrate
scope.
mechanism
investigated
in
detail,
scale-up
experiments
are
performed.
Organic & Biomolecular Chemistry,
Год журнала:
2023,
Номер
21(20), С. 4225 - 4236
Опубликована: Янв. 1, 2023
An
efficient
trifluoromethylation
of
2-isocyanobiaryls
was
developed
through
the
constant
current
electrolysis,
employing
sodium
trifluoromethanesulfinate
(CF3SO2Na)
as
trifluoromethyl
source.
The
method
enabled
syntheses
a
series
6-(trifluoromethyl)phenanthridine
derivatives
in
moderate
to
high
yields
under
metal-
and
oxidant-free
conditions.
A
gram-scale
synthesis
highlights
synthetic
versatility
reported
protocol.
The Journal of Organic Chemistry,
Год журнала:
2021,
Номер
86(22), С. 16187 - 16194
Опубликована: Авг. 26, 2021
Carbohydrates
play
essential
roles
in
various
physiological
and
pathological
processes.
Trifluoromethylated
compounds
have
wide
applications
the
field
of
medicinal
chemistry.
Herein,
we
report
a
practical
efficient
trifluoromethylation
glycals
by
an
electrochemical
approach
using
CF3SO2Na
as
trifluoromethyl
source
MnBr2
redox
mediator.
A
variety
trifluoromethylated
bearing
different
protective
groups
are
obtained
60–90%
yields
with
high
regioselectivity.
The
successful
capture
CF3
radical
indicates
that
mechanism
is
involved
this
reaction.
The Journal of Organic Chemistry,
Год журнала:
2022,
Номер
87(9), С. 5856 - 5865
Опубликована: Апрель 13, 2022
We
investigated
the
electrochemical
sulfenylation
reaction
in
both
batch
and
continuous
flow
regimes,
involving
thiophenols/thiols
enol–acetates
to
yield
α-sulfenylated
ketones,
without
using
additional
oxidants
or
catalysts.
Studies
with
different
electrolytes
were
also
performed,
revealing
that
quaternary
ammonium
salts
are
best
mediators
for
this
reaction.
Notably,
during
study
of
scope,
a
Boc-cysteine
proved
be
extremely
tolerant
our
protocol,
thus
increasing
its
relevance.
The
methodology
scalable
conditions,
opening
up
possibilities
further
studies
since
these
relevant
functional
groups
important
moieties
organic
synthesis.
Organic & Biomolecular Chemistry,
Год журнала:
2022,
Номер
20(47), С. 9362 - 9367
Опубликована: Янв. 1, 2022
A
simple,
efficient
and
environmentally
friendly
transition-metal-free
electrochemical
oxidative
trifluoromethylation/C(sp
2
)–H
functionalization
of
hydrazones
is
explored,
in
which
two
pathways
are
applicable
to
different
substrates.
New Journal of Chemistry,
Год журнала:
2023,
Номер
47(12), С. 5780 - 5785
Опубликована: Янв. 1, 2023
A
novel
and
unprecedented
method
for
the
polychlorinated
alkylation
annulation
of
N
-arylacrylamide
has
been
developed
under
electrochemical
conditions
with
diazo
salt
as
mediator
at
cathode
reduction
CH
2
Cl
substrate
solvent.
Advanced Synthesis & Catalysis,
Год журнала:
2023,
Номер
366(2), С. 214 - 219
Опубликована: Дек. 6, 2023
Abstract
An
iron‐catalyzed
direct
C3−H
radical
trifluoromethylthiolation
of
quinoxalin‐2(1
H
)‐ones
has
been
developed.
This
protocol
uses
earth‐abundant
FeSO
4
⋅
7H
2
O
as
the
catalyst,
and
AgSCF
3
trifluoromethylthiolating
reagent
to
provide
various
SCF
‐containing
)‐one
derivatives
in
26–88%
yields.
Preliminary
mechanistic
investigations
indicate
that
reaction
proceeds
through
a
pathway.
