Chemical Communications,
Journal Year:
2024,
Volume and Issue:
60(75), P. 10358 - 10361
Published: Jan. 1, 2024
Herein,
we
disclose
the
first
reports
on
utilization
of
vinylene
carbonate
as
a
C1
methylene
source
in
ruthenium-catalyzed
additive
controlled
regioselective
C4-methylenation
and
weak
chelation-assisted
C8-formylmethylation
isoquinolinones.
Adopting
both
C2
synthon
is
an
important
highlight
this
work.
Amide
carbonyl
acts
traceless
directing
group
C8-formylmethylation.
Remarkably,
reaction,
two
C-C
bonds
form
one-pot
producing
dimeric
isoquinolinones
by
employing
surrogate
presence
copper
acetate
additive.
Importantly,
unsymmetrical
dimers
were
achievable,
albeit
low
yield.
Extensive
control
experiments
are
conducted
to
decipher
reaction
mechanism.
It
evident
from
mechanistic
studies,
that
formation
formylmethyl
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
magnified
image
Organic & Biomolecular Chemistry,
Journal Year:
2022,
Volume and Issue:
20(48), P. 9604 - 9608
Published: Jan. 1, 2022
An
efficient
metal-free
annulative
vinylene
transfer
protocol
for
the
synthesis
of
benzo-fused
indolizines
via
1,3-dipolar
cycloadditions
N-ylides
with
carbonate
has
been
developed.
Vinylene
serves
as
an
acetylene
surrogate
without
any
external
oxidant
involved.
This
transformation
leads
to
direct
construction
versatile
indolizine
derivatives
in
moderate
good
yields.
Green Chemistry,
Journal Year:
2023,
Volume and Issue:
25(11), P. 4282 - 4291
Published: Jan. 1, 2023
The
chemical
upcycling
of
poly(bisphenol
A
carbonate)
was
carried
out
through
organocatalysis
using
α-hydroxyketones
as
nucleophiles,
leading
to
valuable
vinylene
carbonates.
Advanced Synthesis & Catalysis,
Journal Year:
2023,
Volume and Issue:
365(20), P. 3400 - 3412
Published: Sept. 6, 2023
Abstract
Recently,
vinylene
carbonate
has
been
developed
as
a
powerful
synthon
in
transition
metal‐catalyzed
C−H
bond
activation/cyclization
reactions.
This
review
introduces
recent
progress
the
use
of
reactant,
by
analyzing
and
comparing
reaction
models
involving
surrogate
ethynol,
acetylene,
acetylation
reagents
or
other
reactants,
while
addressing
related
mechanisms
synthetic
applications.
Chemical Communications,
Journal Year:
2024,
Volume and Issue:
60(26), P. 3571 - 3574
Published: Jan. 1, 2024
Herein,
a
novel
Pd-catalyzed
denitrogenation/vinylation
of
benzotriazinones
using
vinylene
carbonate
as
the
vinylation
reagent
is
reported.
This
transformation
demonstrates
an
unprecedented
skeletal
editing
approach,
effectively
converting
NN
to
CC
fragments
The Journal of Organic Chemistry,
Journal Year:
2025,
Volume and Issue:
unknown
Published: April 3, 2025
A
divergent
[5
+
1]
cyclization
reaction
of
o-aminobenzamides
with
vinylene
carbonate
has
been
developed,
rapidly
generating
three
types
cyclic
molecules
including
quinazolinones,
2-methylquinazolinones,
and
2,3-dihydroquinazolinones
high
chemoselectivity.
In
this
discovery,
blooms
as
a
multifunctional
reagent
to
participate
in
cyclization.
The
potential
new
finding
is
further
emphasized
by
assembling
the
benzothiazole
heteroarene
via
[4
version
tolerating
bioactive
units
well.
European Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
26(44)
Published: Sept. 27, 2023
Abstract
A
mild
and
convenient
synthesis
of
3,4‐unsubstituted
isoquinolones
has
been
achieved
from
N
‐methoxybenzamides
vinylene
carbonate
as
an
acetylene
surrogate
with
a
versatile
rhodium(III)
catalyst.
The
reaction
proceeded
at
room
temperature
in
biomass
derived
ethanol
solvent.
This
protocol
avoids
the
use
stoichiometric
external
oxidant,
served
internal
oxidant.
C−H/N−H
activation
annulation
manifold
broad
substrate
scope
excellent
levels
regioselectivities.
preliminary
mechanistic
studies
suggest
facile
reversible
chelation‐assisted
C−H
rhodation.
Diversification
provide
access
to
4‐substituted
isoquinolines,
which
are
complementary
previously
reported
protocols.
RSC Advances,
Journal Year:
2024,
Volume and Issue:
14(7), P. 4804 - 4809
Published: Jan. 1, 2024
The
step-economical
synthesis
of
C2,
C3-unsubstituted
1-aminoindole
derivatives
through
rhodium-catalyzed
annulation
hydrazines
with
vinylene
carbonate.
The Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
unknown
Published: Dec. 5, 2024
The
development
of
novel
directing
groups
is
a
valuable
strategy
to
secure
the
advancement
catalytic
C-H
functionalization.
To
illustrate
feasibility
urazoles
as
heterocyclic
groups,
we
herein
present
ruthenium(II)-catalyzed
annulation
N-H/C-H
bonds
on
