Advanced Synthesis & Catalysis,
Journal Year:
2021,
Volume and Issue:
364(4), P. 838 - 844
Published: Dec. 17, 2021
Abstract
A
convenient
and
effective
method
of
ruthenium‐catalyzed
C−H/N−H
annulations
using
vinylene
carbonate
as
oxidizing
acetylene
surrogate
has
been
disclosed.
This
is
scalable
compatible
with
a
wide
range
functional
groups,
providing
step‐economical
access
to
indole
synthesis
Preliminary
mechanistic
studies
provided
support
for
reversible,
acetate‐assisted
C−H
ruthenation,
along
subsequent
olefin
insertion.
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Synthesis,
Journal Year:
2021,
Volume and Issue:
53(21), P. 3935 - 3950
Published: July 12, 2021
gem-Difluoroalkenes
are
readily
available
fluorinated
building
blocks,
and
the
fluorine-induced
electronic
perturbations
of
alkenes
enables
a
wide
array
selective
functionalization
reactions.
However,
many
reactions
gem-difluoroalkenes
result
in
net
C─F
to
generate
monofluorovinyl
products
or
addition
F
trifluoromethyl-containing
products.
In
contrast,
fluorine-retentive
strategies
for
remain
less
generally
developed,
is
now
becoming
rapidly
developing
area.
This
review
will
present
development
including
electrophilic,
nucleophilic,
radical,
transition
metal
catalytic
with
an
emphasis
on
key
physical
organic
mechanistic
aspects
that
enable
reactivities.
The Journal of Organic Chemistry,
Journal Year:
2021,
Volume and Issue:
86(24), P. 18204 - 18210
Published: Nov. 25, 2021
Manganese-catalyzed
C-H
bond
functionalization
of
aryl
amidines
for
the
synthesis
1-aminoisoquinolines
in
presence
vinylene
carbonate
has
been
developed.
The
reaction
features
a
broad
substrate
scope
and
proceeds
under
mild
conditions
with
only
anion
as
byproduct.
Organic Letters,
Journal Year:
2022,
Volume and Issue:
24(14), P. 2613 - 2618
Published: April 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.
Organic Letters,
Journal Year:
2022,
Volume and Issue:
24(31), P. 5679 - 5683
Published: July 28, 2022
Benzofuran
is
a
privileged
structure
in
many
bioactive
compounds;
however,
the
controlled
synthesis
of
C2,C3-nonsubstituted
benzofurans
has
been
scarce.
In
particular,
cumbersome
multistep
processes
are
inevitable
for
most
inaccessible
C4-substituted
isomers.
Herein,
we
report
Rh-catalyzed
direct
vinylene
annulation
readily
available
m-salicylic
acid
derivatives
with
carbonate
to
achieve
selective
construction
benzofurans.
The
Weinreb
amide
directing
group
facilitated
following
product
derivatization.
reaction
mechanism
was
investigated
by
DFT
calculations.
Chemical Communications,
Journal Year:
2022,
Volume and Issue:
58(28), P. 4476 - 4479
Published: Jan. 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,
Journal Year:
2022,
Volume and Issue:
364(9), P. 1580 - 1586
Published: April 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.
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image
Organic Chemistry Frontiers,
Journal Year:
2023,
Volume and Issue:
10(22), P. 5717 - 5734
Published: Jan. 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,
Journal Year:
2023,
Volume and Issue:
365(9), P. 1457 - 1464
Published: April 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
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