Asian Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
12(9)
Published: July 31, 2023
Abstract
Secondary
trifluoromethylated
alkyl
bromides
are
versatile
building
blocks
in
the
synthesis
of
fluorine‐containing
aliphatic
compounds.
However,
current
methods
preparation
limited.
In
this
study,
we
have
developed
a
general
deaminative
cross‐coupling
Katritzky
salts
with
2‐bromo‐3,3,3‐trifluoropropene
(BTP)
as
route
to
α‐trifluoromethylated
that
is
driven
by
an
electron‐donor‐acceptor
(EDA)
complex.
The
resultant
products
can
be
readily
converted
α‐trifluoromethyl
borates
and
alcohols,
enriching
toolbox
for
synthesizing
compounds
wide‐ranging
applications.
Angewandte Chemie International Edition,
Journal Year:
2023,
Volume and Issue:
62(49)
Published: Aug. 22, 2023
Abstract
Much
progress
has
been
made
in
the
development
of
methods
to
both
create
compounds
that
contain
C−F
bonds
and
functionalize
bonds.
As
such,
are
becoming
common
versatile
synthetic
functional
handles.
This
review
summarizes
advantages
defluorinative
functionalization
reactions
for
small
molecule
synthesis.
The
coverage
is
organized
by
type
carbon
framework
fluorine
attached
mono‐
polyfluorinated
motifs.
main
challenges,
opportunities
advances
discussed
each
class
organofluorine.
Most
text
focuses
on
case
studies
illustrate
how
defluorofunctionalization
can
improve
routes
targets
or
properties
enable
unique
mechanisms
reactions.
broader
goal
showcase
incorporating
exploiting
design
routes,
improvement
specific
advent
new
methods.
The Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
88(4), P. 2631 - 2641
Published: Feb. 3, 2023
An
efficient,
catalyst-
and
additive-free,
visible-light-driven
radical
C3-H
alkylation
of
quinoxalin-2(1H)-one
derivatives
has
been
developed.
This
reaction
utilizes
alkyl-NHP-esters
as
an
alkyl
donor
acceptor.
The
operationally
simple
protocol
works
under
mild
conditions
tolerates
a
variety
functional
groups.
Furthermore,
the
synthetic
utility
methodology
was
successfully
implemented
for
synthesizing
biologically
relevant
C3-alkyl
substituted
derivatives.
Angewandte Chemie International Edition,
Journal Year:
2024,
Volume and Issue:
63(13)
Published: Jan. 18, 2024
Abstract
Trifluoromethyl
cationic
carbyne
(CF
3
C
+
:)
possessing
dual
carbene‐carbocation
behavior
emulated
as
trifluoromethyl
metal‐carbynoid
=M)
has
not
been
explored
yet,
and
its
reaction
characteristics
are
unknown.
Herein,
a
novel
α‐diazotrifluoroethyl
sulfonium
salt
was
prepared
used
in
Rh‐catalyzed
three‐component
[2+1+2]
cycloadditions
for
the
first
time
with
commercially
available
N
‐fused
heteroarenes
nitriles,
yielding
series
of
imidazo[1,5‐
]
‐heterocycles
that
interest
medicinal
chemistry,
which
insertion
Rh‐carbynoid
=Rh)
into
C=N
bonds
involved.
This
strategy
demonstrates
synthetic
applications
late‐stage
modification
pharmaceuticals,
construction
CD
‐containing
‐heterocycles,
gram‐scale
experiments,
synthesis
phosphodiesterase
10A
inhibitor
analog.
These
highly
valuable
modifiable
exhibit
good
antitumor
activity
vitro,
thus
demonstrating
their
potential
chemistry.
Asian Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
12(2)
Published: Jan. 11, 2023
Abstract
We
developed
a
novel
and
efficient
method
for
the
synthesis
of
various
3‐alkylated
quinoxalin‐2(1
H
)‐ones
(32
examples,
70%–96%
yields)
through
electron
donor‐acceptor
complex
enabled
alkylation
with
N
‐
hydroxyphthalimide
esters
as
alkyl
source
Na
2
S
catalytic
donor
under
external
photocatalyst‐,
oxidant‐
additive‐free
conditions.
Organic Chemistry Frontiers,
Journal Year:
2023,
Volume and Issue:
10(8), P. 1981 - 1987
Published: Jan. 1, 2023
A
photoinduced
radical
[1,2]-Brook
rearrangement/defluorinated
alkylation
reaction
of
α-trifluoromethyl
alkenes
with
α-silyl
alcohols
was
developed
for
facile
access
to
gem
-difluoro
homoallylic
alcohol
derivatives.
Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(15), P. 3097 - 3102
Published: April 4, 2024
This
study
introduces
a
novel
approach
involving
XB-mediated
cross-coupling
of
α-trifluoromethylated
alkyl
bromides
with
coumarins
and
quinolinones
under
visible
light
irradiation.
Both
density
functional
theory
(DFT)
calculations
experimental
studies
converge
to
suggest
that
the
noncovalent
interaction
between
DMAP,
intensified
by
α-trifluoromethyl
group,
plays
pivotal
role
in
facilitating
this
chemoselective
reaction.
ACS Catalysis,
Journal Year:
2023,
Volume and Issue:
13(13), P. 8624 - 8630
Published: June 14, 2023
CF3-containing
molecules
are
frequently
encountered
in
many
best-selling
pharmaceutical
drugs.
Consequently,
a
large
number
of
methods
have
been
developed
for
introducing
CF3
group
into
organic
compounds.
However,
innovative
protocols
enabling
direct
access
to
alkyl-CF3
moieties
still
sought
after.
In
this
context,
we
report
visible-light-induced
formal
trifluoropropanation
various
alkyl
and
aryl
halide
derivatives
using
the
2-Bromo-3,3,3-trifluoro-1-propene
(BTP)
as
readily
available
building
block.
Our
strategy
relies
on
use
catalytic
system
merging
amount
supersilane
NaBH4
an
additional
reductant.
These
mild
reaction
conditions
compatible
with
range
functional
groups.
Finally,
double
deuterium
incorporation
was
obtained
upon
replacement
NaBD4
under
these
conditions,
leading
formation
hitherto
unknown
α,α-d2-CF3
Chemistry - A European Journal,
Journal Year:
2025,
Volume and Issue:
unknown
Published: Jan. 22, 2025
We
have
developed
an
efficient
synthesis
of
fluoroalkenes
via
tandem
electrochemical
dehalogenation-elimination
protocol.
The
key
step
is
the
generation
carbon
anion
by
reductive
dehalogenation
alkyl
halides.
Various
gem-difluoroalkenes
and
monofluoroalkenes
were
prepared
in
moderate
to
good
yields
from
α-difluoromethylated/α-trifluoromethylated
benzyl
