Angewandte Chemie,
Год журнала:
2023,
Номер
135(32)
Опубликована: Июнь 20, 2023
Abstract
Direct
synthesis
of
gem
‐difluorinated
carbocyclic
molecules
represents
a
longstanding
challenge
in
organic
chemistry.
Herein,
Rh‐catalyzed
[3+2]
cycloaddition
reaction
between
readily
available
cyclopropanes
(
‐DFCPs)
and
internal
olefins
has
been
developed,
enabling
the
efficient
cyclopentanes
with
good
functional
group
compatibility,
excellent
regioselectivity
diastereoselectivity.
The
resulting
products
can
undergo
downstream
transformations
to
access
various
mono‐fluorinated
cyclopentenes
cyclopentanes.
This
demonstrates
use
‐DFCPs
as
type
“CF
2
”
C3
synthon
for
under
transition
metal
catalysis,
which
provides
potential
strategy
synthesizing
other
molecules.
Journal of the American Chemical Society,
Год журнала:
2024,
Номер
146(2), С. 1722 - 1731
Опубликована: Янв. 4, 2024
Herein,
we
report
a
ligand-controlled
palladium-catalyzed
method
that
enables
the
synthesis
of
ynones
and
γ-butenolides
with
excellent
regioselectivity
from
same
set
readily
available
aryl
iodides,
acetylenes,
BrCF2CO2K.
In
this
reaction,
[PdII]═CF2
does
demonstrate
electrophilicity
can
generate
CO
when
reacting
H2O.
It
is
environmentally
friendly
safe
compared
to
traditional
methods,
current
protocol
us
afford
in
high
yields
functionality
tolerance.
Moreover,
esters
also
be
obtained
corresponding
phenols
alcohols
utilizing
strategy.
The
success
late-stage
functionalization
bioactive
compounds
further
illustrates
synthetic
utility
material
development
drug
discovery.
Angewandte Chemie International Edition,
Год журнала:
2023,
Номер
62(32)
Опубликована: Июнь 20, 2023
Direct
synthesis
of
gem-difluorinated
carbocyclic
molecules
represents
a
longstanding
challenge
in
organic
chemistry.
Herein,
Rh-catalyzed
[3+2]
cycloaddition
reaction
between
readily
available
cyclopropanes
(gem-DFCPs)
and
internal
olefins
has
been
developed,
enabling
the
efficient
cyclopentanes
with
good
functional
group
compatibility,
excellent
regioselectivity
diastereoselectivity.
The
resulting
products
can
undergo
downstream
transformations
to
access
various
mono-fluorinated
cyclopentenes
cyclopentanes.
This
demonstrates
use
gem-DFCPs
as
type
"CF2
"
C3
synthon
for
under
transition
metal
catalysis,
which
provides
potential
strategy
synthesizing
other
molecules.
Organic Letters,
Год журнала:
2023,
Номер
25(39), С. 7214 - 7219
Опубликована: Сен. 26, 2023
A
novel
Rh(III)-catalyzed
cascade
alkenyl
C-H
activation/[3
+
2]
annulation/pinacol
rearrangement
reaction
of
enaminones
with
iodonium
ylides
has
been
developed.
This
methodology
provides
a
new
and
straightforward
synthetic
strategy
to
afford
highly
functionalized
2-spirocyclo-pyrrol-3-ones
in
satisfactory
yield
from
readily
available
starting
materials
under
mild
conditions.
Moreover,
gram-scale
reactions
further
derivatization
experiments
are
implemented
demonstrate
the
potential
utility
this
developed
approach.
Science China Chemistry,
Год журнала:
2022,
Номер
66(1), С. 139 - 146
Опубликована: Дек. 12, 2022
Abstract
Fluorinated
heterocycles
play
a
vital
role
in
pharmaceutical
and
agrochemical
industries.
Hence,
rapid
efficient
construction
of
fluorinated
remains
highly
demanded.
Herein,
difluoroalkylative
carbonylative
cyclization
unactivated
alkenes
ethylene
gas
enabled
by
palladium
catalysis
has
been
developed
for
the
first
time
toward
synthesis
α-carbonyl
difluoro-modified
glutarimides.
This
procedure
can
also
be
applied
to
GeMigliptin
which
is
medicine
approved
treatment
type
2
diabetes
mellitus.
Chemistry - A European Journal,
Год журнала:
2023,
Номер
29(28)
Опубликована: Фев. 24, 2023
Using
benzylamines
as
the
C4
source
of
1,4-dihydropyridines
(1,4-DHPs),
a
Cu-catalyzed
oxidative
[1+2+1+2]
cascade
cyclization
for
synthesis
1,4-DHPs
was
firstly
developed.
A
broad
range
easily
available
N,N-dimethyl
enaminones
and
are
employed
smoothly
to
provide
diverse
with
high
efficiency.
This
method
is
performed
by
one-pot
C(sp3
)-H
bond
functionalization/C(sp3
)-N
cleavage/cyclization
strategy
form
simultaneously
two
)-C(sp2
)
bonds,
C(sp2
1,4-DHP
ring.
Organic Letters,
Год журнала:
2023,
Номер
25(16), С. 2868 - 2872
Опубликована: Апрель 19, 2023
Difluorocarbene-triggered
[1+5]
annulation
is
developed
to
access
1,1-difluoro-1,9a-dihydropyrido[2,1-c][1,4]thiazine-3,4-dicarboxylate
derivatives
in
satisfactory
good
yields
via
the
direct
reaction
of
potassium
bromodifluoroacetate
and
pyridinium
1,4-zwitterionic
thiolates
under
heating.
Pyridinium
first
nucleophilically
attack
difluorocarbene
generated
from
followed
by
an
intramolecular
nucleophilic
addition
pyridiniums.
This
method
provides
expeditious
route
introduce
difluoromethyl
group
into
1,9a-dihydropyrido[2,1-c][1,4]thiazine
ring,
even
modify
drug
molecules.
Advanced Synthesis & Catalysis,
Год журнала:
2022,
Номер
364(20), С. 3539 - 3543
Опубликована: Авг. 26, 2022
Abstract
A
photoinduced
multicomponent
reaction
of
arylamines,
enaminones
and
difluorobromoacetates
for
the
synthesis
2,3‐difunctionalized
quinolines
is
reported.
This
strategy
features
broad
functional
groups
tolerance
wide
substrate
scopes
that
enables
further
synthetic
applications
obtained
products.
Mechanistic
studies
reveal
intermolecular
[3+3]
cyclization
between
in‐situ
generated
1,3‐vinylimine
ions
arylamines
key
step
in
this
transformation.
magnified
image
Advanced Synthesis & Catalysis,
Год журнала:
2022,
Номер
364(24), С. 4440 - 4446
Опубликована: Дек. 2, 2022
Abstract
A
silver‐catalyzed
protocol
for
the
synthesis
of
3‐(1
H
‐isochromen)‐chromones
is
described.
The
method
involves
an
initial
6‐endo‐dig
cyclization
o
‐alkynylbenzaldehydes
and
domino
C−H
alkylation
chromone
annulation
‐hydroxyarylenaminones,
which
enables
installation
1
‐isochromen
in
a
single
structure.
This
synthetic
strategy
advantageous
excellent
regioselectivity,
step
economy,
concise
one‐pot
methodology,
gram‐scale
synthesis,
as
well
high
bond‐forming
efficiency.
magnified
image
