Organic Letters,
Journal Year:
2023,
Volume and Issue:
25(38), P. 7057 - 7061
Published: Sept. 13, 2023
A
TFA-catalyzed
dehydrofluorinative
cyclization
of
2,2-difluoro-3-hydroxy-1,4-diketones
has
been
developed
in
the
presence
amines
under
mild
conditions
which
difluorinated
substrates
are
readily
prepared
according
to
our
reported
literature.
This
protocol
provides
a
rapid
construction
fluoro
3(2H)-furanones
good
excellent
yields
with
functional
group
tolerance.
Easy
scale-up
synthesis
also
shows
practical
advantage.
The Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
89(5), P. 2847 - 2857
Published: Feb. 16, 2024
In
recent
years,
the
application
of
fluorinated
alcohols
as
solvents,
cosolvents,
or
additives
has
become
important
in
modern
organic
synthesis.
However,
their
potential
efficient
catalysts
synthesis
not
been
well-explored.
this
article,
we
report
on
development
a
one-pot
sequential
cascade
reaction
p-quinone
methides
with
difluoroenoxysilanes
using
hexafluoroisopropanol
catalyst.
This
allows
for
preparation
multisubstituted
oxa-spiro[4,5]cyclohexadienones.
By
50
mol
%
1,1,1,3,3,3-Hexafluoroisopropanol
(HFIP),
proceeds
smoothly
to
yield
1,6-conjugated
products,
which
are
then
subjected
oxidative
dearomatization/hemiacetalization
PhI(OAc)2.
The
overall
process
affords
moderate
high
yields
and
excellent
diastereoselectivities.
The Journal of Organic Chemistry,
Journal Year:
2025,
Volume and Issue:
unknown
Published: Feb. 18, 2025
A
hexafluoroisopropanol
(HFIP)-promoted
hydrodifluoroalkylation
of
furans
and
vinyl
ethers
with
difluorinated
silyl
enol
has
been
developed.
Because
the
inherent
electron
richer
nature
poor
nucleophilicity
ethers,
employment
simple
as
substrates
for
nucleophilic
dearomatization
without
a
metal
or
stoichiometric
chemical
oxidizing
reagent
is
challenging,
especially
considering
rearomatization
driving
force
ring
fragmentation
furan
system.
This
protocol
exploits
formation
oxocarbenium
intermediate
from
using
HFIP
proton
source
to
allow
addition
which
provides
an
efficient
synthetic
strategy
install
gem-difluorinated
group
into
heterocycles.
Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(31), P. 6551 - 6555
Published: July 30, 2024
The
asymmetric
Mannich-type
reaction
of
quinoxalin-2-ones
with
difluoroenoxysilanes
has
been
developed
for
the
synthesis
chiral
gem-difluoroalkylated
quinoxalin-2-ones.
worked
in
presence
phosphoric
acid
CPA
1
and
B(C6F5)3
THF
at
room
temperature.
exhibited
a
good
substrate
scope
furnishing
products
yields
(up
to
97%)
up
96%
ee.
The Journal of Organic Chemistry,
Journal Year:
2025,
Volume and Issue:
unknown
Published: March 27, 2025
Herein,
we
present
an
acid-
and
base-mediated
approach
for
ring
opening
of
donor-acceptor
cyclopropanes
(DACs)
followed
by
(3+2)
annulation,
yielding
biologically
relevant
gem-difluorinated
cyclopentenes
via
α,α-difluoroketone
scaffolds.
Fluorinated
rings
are
essential
building
blocks
in
drug
discovery
materials
research.
This
methodology
has
a
broad
substrate
scope,
is
scalable,
provides
practical
synthetic
route
to
obtain
value-added
fluorinated
compounds.
ChemistryEurope,
Journal Year:
2025,
Volume and Issue:
unknown
Published: April 17, 2025
A
mechanochemical
strategy
for
promoting
copper‐catalyzed
solid‐state
radical
C–H
difluoroalkylation
reactions
has
been
devised.
Compared
to
traditional
solution‐based
methods,
this
mechanoredox
approach
offers
enhanced
ease
of
handling,
greater
cleanliness,
and
improved
sustainability
the
synthesis
difluoroalkylated
indoles,
which
constitute
crucial
structural
motifs
in
contemporary
drug
discovery.
The
underlying
reaction
mechanism
is
investigated
through
meticulous
step‐by‐step
control
experiments
that
highlighted
substantial
influence
conditions.
versatility
protocol
demonstrated
by
its
applications
complex
natural
products
derivatives.
The Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
89(18), P. 13457 - 13471
Published: Sept. 3, 2024
Organic
molecules
containing
a
difluoroalkyl
group
are
valuable
and
versatile
chemicals
because
of
their
unique
physicochemical
biological
properties.
Accordingly,
the
development
efficient
practical
difluoroalkylation
for
preparation
these
compounds
is
important
attractive.
Herein,
we
demonstrate
photoredox-catalyzed
base-dependent
selective
carbodifluoroalkylation
halodifluoroalkylation
alkenes
using
readily
available
2-(allyloxy)arylaldehydes
[or
2-(allylamino)arylaldehydes]
XCF
Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(31), P. 6742 - 6747
Published: July 26, 2024
Fluorinated
rings
have
emerged
as
privileged
structural
modules
in
the
fields
of
drug
discovery
and
materials
research.
The
incorporation
fluorine
atoms
into
aromatic
or
heterocycles
can
lead
to
significant
improvements
physicochemical
biological
properties
small
molecules,
making
them
valuable
components
design
new
drugs
functional
materials.
Herein,
we
presented
a
cobalt-catalyzed
C–H
oxidation/gem-difluorination
cascade
reaction
readily
available
cyclic
ethers
with
difluoroenoxysilanes,
affording
series
gem-difluorinated
analogues
moderate
high
yields.
obtained
products
versatile
fluoroalkyl
building
blocks
were
showcased
through
divergent-oriented
transformations.
The Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
89(20), P. 14940 - 14950
Published: Oct. 9, 2024
An
electrochemical
Giese-type
hydrothiolation
of
α-trifluoromethylstyrenes
with
disulfides
is
disclosed
for
the
first
time
under
metal-free
and
mild
conditions.
This
approach
provides
a
facile
methodology
β-trifluoromethylated
thioethers
in
moderate
to
good
yields
high
functional
group
tolerance
starting
from
readily
available
substrates.
Additionally,
late-stage
modification
drug
molecules
gram-scale
synthesis
show
practical
advantages.
The
radical
pathway
this
reaction
has
been
revealed
by
control
experiments
cyclic
voltammetry
measurements.
