Beilstein Journal of Organic Chemistry,
Год журнала:
2024,
Номер
20, С. 2691 - 2703
Опубликована: Окт. 24, 2024
In
this
study,
we
develop
the
synthesis
methods
of
fluoroalkenes
and
fluoroenynes
via
Suzuki–Miyaura
Sonogashira
cross-coupling
reactions
using
novel
multihalogenated
fluorovinyl
ethers,
which
are
easily
prepared
from
reaction
between
phenols
2-bromo-2-chloro-1,1,1-trifluoroethane
(halothane).
These
make
use
unique
structure
contains
a
reactive
bromine
atom,
to
afford
series
in
moderate
high
yields.
Angewandte Chemie International Edition,
Год журнала:
2023,
Номер
62(42)
Опубликована: Авг. 12, 2023
Abstract
An
unprecedented
Pd‐catalyzed
fluorinative
bifunctionalization
of
aziridines
and
azetidines
was
successfully
developed
via
regioselective
C−C
C−F
bond
cleavage
gem‐difluorocyclopropanes,
leading
to
various
β,β′‐bisfluorinated
amines
β,γ‐bisfluorinated
amines.
This
reaction
achieved
by
incorporating
a
2‐fluorinated
allyl
group
fluorine
atom
scissored
from
gem‐difluorocyclopropane
in
100
%
economy
for
the
first
time.
The
mechanistic
investigations
indicated
that
underwent
amine
attacking
palladium
complex
generate
η
2
‐coordinated
N‐allyl
aziridine
followed
fluoride
ligand
transfer
affording
final
β‐
γ‐fluorinated
Angewandte Chemie International Edition,
Год журнала:
2024,
Номер
63(11)
Опубликована: Янв. 10, 2024
Here
we
present
a
modular,
chemo-,
regio-,
and
stereoselective
synthesis
of
fully-substituted
configuration-defined
alkyl
vinyl
ethers
(AVEs)
using
simple
chemical
feedstocks.
The
distinctive
approach
involves
the
chemo-
regioselective
functionalization
CF
Chemical Communications,
Год журнала:
2024,
Номер
60(28), С. 3764 - 3773
Опубликована: Янв. 1, 2024
This
feature
article
summarizes
our
efforts
towards
developing
Rh-catalyzed
reactions
of
gem
-difluorinated
cyclopropanes,
briefly
discussing
the
design,
selectivity,
mechanisms
and
future
research
prospects.
Organic Letters,
Год журнала:
2023,
Номер
25(28), С. 5220 - 5225
Опубликована: Июль 12, 2023
An
efficient
palladium-catalyzed
2-fluoroallylation
of
P(O)H
compounds
with
gem-difluorocyclopropanes
is
presented.
The
reaction
provides
a
variety
2-fluoroallylic
phosphorus
in
good
yields
high
Z
selectivity
through
the
sequential
C-C
bond
activation,
C-F
cleavage,
and
C-P
coupling
process.
Various
H-phosphonates,
H-phosphinates,
secondary
phosphine
oxides
are
all
tolerated.
In
addition,
gram-scale
synthesis
late-stage
modification
complex
bioactive
molecules
show
practical
utilities
transformation.
Organic Letters,
Год журнала:
2024,
Номер
26(8), С. 1672 - 1676
Опубликована: Фев. 15, 2024
The
(3
+
2)
cycloaddition/sulfur
rearrangement
reaction
of
donor–acceptor
cyclopropanes
bearing
a
single
keto
acceptor
with
indoline-2-thiones
has
been
realized.
Under
the
catalysis
Sn(OTf)2,
series
functionalized
3-indolyl-4,5-dihydrothiophenes
were
synthesized
moderate
to
excellent
yields.
Organic Letters,
Год журнала:
2023,
Номер
25(50), С. 9020 - 9024
Опубликована: Дек. 8, 2023
This
study
presents
a
novel
method
for
the
regioselective
coupling
of
gem-difluorinated
cyclopropanes
with
gem-diborylmethane,
utilizing
Pd-catalyst
system.
innovative
approach
enables
synthesis
2-fluoroalkenyl
monoboronate
scaffolds
high
Z-selectivity.
The
resulting
products
undergo
further
transformations,
including
oxidation,
Suzuki
cross-coupling,
and
trifluoroborylation,
all
which
are
achieved
good
yields.
work
introduces
valuable
synthetic
pathway
to
access
important
fluorinated
compounds
various
applications
in
organic
chemistry.
Chemical Science,
Год журнала:
2024,
Номер
15(34), С. 13800 - 13806
Опубликована: Янв. 1, 2024
Metathesis
reactions
have
been
established
as
a
powerful
tool
in
organic
synthesis.
While
great
advances
were
achieved
double-bond
metathesis,
like
olefin
metathesis
and
carbonyl
single-bond
has
received
less
attention
the
past
decade.
Herein,
we
describe
first
C(sp
Organic Letters,
Год журнала:
2024,
Номер
26(32), С. 6905 - 6909
Опубликована: Авг. 1, 2024
We
present
a
palladium-catalyzed
ring-opening
reaction
that
induces
indoles
to
cross-couple
with
gem-difluorocyclopropanes.
The
proceeds
through
domino
process
of
C–C
bond
activation
and
C–F
elimination,
followed
by
C–C(sp2)
coupling
produce
various
2-fluoroallylindoles.
This
method
is
characterized
its
high
functional
group
tolerance,
good
yields
regioselectivity,
under
base-free
conditions.
synthetic
utility
the
products
illustrated
functionalization
NH
C2
positions
indole
scaffold.
A
nickel-catalyzed
reductive
cross-coupling
of
gem-bromofluorocyclopropanes
with
aryl
bromides
for
the
synthesis
monofluorinated
cyclopropane
derivatives
is
reported.
Different
from
cleavage
route
ring
reported
by
previous
works,
this
catalytic
system
shows
excellent
regioselectivity
control
cyclic
selectivity,
giving
as
major
product.
This
transformation
demonstrates
mild
conditions,
high
efficiency,
a
broad
substrate
scope,
and
good
functional
group
compatibility,
providing
facile
method
diversified
cyclopropane-containing
drugs
bioactive
molecules.
