Organic Letters,
Год журнала:
2021,
Номер
23(21), С. 8527 - 8532
Опубликована: Окт. 20, 2021
Here
we
report
a
novel
Rh-catalyzed
C−H/C−H
alkenylation
of
N-arylmethanimines
with
vinylene
carbonate
acting
as
unit.
Forty
examples
C3,C4-nonsubstituted
quinolines
were
achieved
from
commercially
available
starting
materials.
This
identified
process
features
an
exceedingly
simple
system,
lower
loading
catalyst,
and
the
capacity
for
postfunctionalization
bioactive
molecules.
Advanced Synthesis & Catalysis,
Год журнала:
2021,
Номер
364(3), С. 512 - 517
Опубликована: Ноя. 30, 2021
Abstract
The
rhodium(III)‐catalyzed
C−H
bond
activation
and
vinylene
transfer
of
enaminones
with
carbonate
have
been
proposed
for
the
synthesis
substituted
1‐hydroxy‐2‐naphthaldehydes
in
49–84%
yields.
Several
preliminary
mechanistic
studies
hydroxyl‐directed
derivatization
reactions
were
also
performed.
This
method
offers
an
alternative
approach
1‐hydroxy‐2‐naphthaldehydes.
magnified
image
Organic Letters,
Год журнала:
2021,
Номер
23(14), С. 5518 - 5522
Опубликована: Июль 6, 2021
The
Rh(III)-catalyzed
C–H
functionalization
and
subsequent
intramolecular
cyclization
between
azobenzenes
vinylene
carbonate
is
described
herein.
Depending
on
the
electronic
property
of
azobenzenes,
this
transformation
results
in
formation
(2H)-indazoles
or
dihydrocinnolin-4-ones
through
generation
ortho-alkylated
azo-intermediates
followed
by
decarboxylation.
Surprisingly,
acts
as
an
acetaldehyde
acetyl
surrogate
to
enable
[4
+
1]
2]
annulation
reaction.
This
characterized
its
mild
reaction
conditions,
simplicity,
excellent
functional
group
compatibility.
Organic Letters,
Год журнала:
2022,
Номер
24(14), С. 2613 - 2618
Опубликована: Апрель 4, 2022
A
rhodium-catalyzed
cyclization
of
azobenzenes
and
vinylene
carbonate
via
C-H
bond
activation
to
construct
indazolo[2,3-a]quinolines
has
been
developed.
This
protocol
offers
an
efficient
method
for
synthesis
the
titled
products
in
good
yields
with
broad
functional
group
tolerance.
In
this
reaction,
three
C-C
bonds
C-N
are
formed
one
pot,
(VC)
acts
as
C1
C2
synthons
well
"vinylene
transfer"
agent
acylation
reagent
construction
target-fused
heterocycles.
Moreover,
exhibit
favorable
fluorescence
properties,
which
indicate
their
potential
application
fluorescent
materials
biosensors.
Chemical Communications,
Год журнала:
2022,
Номер
58(28), С. 4476 - 4479
Опубликована: Янв. 1, 2022
A
ruthenium-catalyzed
oxidative
coupling
of
vinylene
carbonate
with
isoxazoles
has
been
developed
to
achieve
the
direct
C-H
formylmethylation
a
diverse
array
arylisoxazoles
utilizing
isoxazole
ring
as
directing
group.
simple
manipulation
established
reaction
conditions
leads
formation
fused-anthranils.
Importantly,
functions
both
formylmethyl
cation
equivalent
through
decarboxylation
process
and
an
acetylene
equivalent.
Control
experiments
were
conducted
elucidate
plausible
mechanism.
This
methodology
is
expected
provide
facile
expeditious
approach
for
synthesis
Advanced Synthesis & Catalysis,
Год журнала:
2022,
Номер
364(9), С. 1580 - 1586
Опубликована: Апрель 1, 2022
Abstract
The
ruthenium‐catalyzed
C7‐formylmethylation
or
sequential
acetalization
of
indolines
with
vinylene
carbonate
has
been
realized
under
simple
and
easy‐to‐operate
reaction
systems.
Several
preliminary
mechanistic
studies
derivatization
reactions
for
the
conversion
formylmethyl
group
were
also
performed.
This
transformation
offers
an
alternative
approach
direct
C(
sp
2
)−H
to
corresponding
acetal
structure.
magnified
image
Organic Chemistry Frontiers,
Год журнала:
2023,
Номер
10(22), С. 5717 - 5734
Опубликована: Янв. 1, 2023
Vinylene
carbonate
(VC)
has
emerged
as
a
promising
coupling
partner
to
participate
in
various
attractive
C–H
conversions
and
implement
an
increasing
number
of
novel
reactions.
In
this
review,
we
provide
summary
the
advancements
achieved
metal-catalyzed
functionalization
using
VC.
Advanced Synthesis & Catalysis,
Год журнала:
2023,
Номер
365(9), С. 1457 - 1464
Опубликована: Апрель 14, 2023
Abstract
In
this
study,
Rh(III)‐catalyzed
C−H
bifunctionalization
and
direct
vinylene
annulation
of
sulfoxonium
ylides
N
‐carbamoylindoles
with
carbonate
was
accomplished,
which
afforded
a
series
naphthalenones
containing
β‐ketosulfoxonium
ylide
moiety,
isocoumarins,
pyrimidones.
This
protocol
featured
mild
conditions,
broad
substrate
scope,
functional‐groups
compatibility.
addition,
related
applications
preliminary
mechanistic
exploratory
were
also
investigated
magnified
image
Organic Letters,
Год журнала:
2021,
Номер
23(22), С. 8910 - 8915
Опубликована: Ноя. 10, 2021
Chemical
transformation
with
vinylene
carbonate
as
an
emerging
synthetic
unit
has
recently
attracted
considerable
attention.
This
report
is
a
novel
conversion
pattern
carbonate,
in
which
such
vibrant
reagent
unprecedentedly
acts
difunctional
coupling
partner
to
complete
the
C-H
annulation
of
free
anilines.
From
commercially
available
substrates,
this
protocol
leads
rapid
construction
synthetically
versatile
2-methylquinoline
derivatives
(43
examples)
excellent
functionality
tolerance.
