Asian Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
unknown
Published: Oct. 29, 2024
Abstract
The
C3‐alkenylation
of
indoles
have
been
developed
by
means
a
novel
in
situ
iodination
tactic
which
is
capable
mediating
the
Heck
coupling
with
alkenes.
method
features
specific
site‐selectivity
oriented
C−I
bond,
high‐step
efficiency
without
pre‐functionalization
for
C‐halogen
bond
construction,
as
well
highly
general
tolerance
to
different
terminal
alkenes,
including
unactivated
acrylates,
acrylic
acid,
vinyl
sulfone
functionalized
natural
products.
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.
magnified
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
magnified
image
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.
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:
2023,
Volume and Issue:
88(11), P. 7281 - 7289
Published: May 19, 2023
A
novel
protocol
for
synthesizing
N-alkyl
indoles
from
readily
available
N-nitrosoanilines
and
iodonium
ylides
through
the
rhodium(III)-catalyzed
C-H
bond
activation/intramolecular
cyclization
reaction
has
been
described.
This
strategy
employs
nitroso
as
a
traceless
directing
group.
The
transformation
features
powerful
reactivity,
tolerates
various
functional
groups,
proceeds
with
moderate
yields
under
mild
conditions,
providing
straightforward
approach
to
access
structurally
diverse
valuable
indole
derivatives.
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.
The Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
89(5), P. 3238 - 3250
Published: Feb. 14, 2024
A
Co(III)-catalyzed
vinylene
transfer
reaction
enabled
by
carboxylic
acid
is
presented.
This
redox-neutral
transformation
tolerates
various
functional
groups,
including
free
hydroxyl
and
features
practicality.
Five-step
routes
based
on
the
Heck
annulation
have
been
devised
to
total
synthesis
of
8-oxodehydrodiscretamine
2-demethyl-oxypalmatine
without
protection
functionality.
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.
