Molecules,
Journal Year:
2023,
Volume and Issue:
28(13), P. 5014 - 5014
Published: June 27, 2023
In
this
study,
we
report
the
synthesis
of
unsubstituted
1,2-benzothiazines
through
a
redox-neutral
Rh(III)-catalyzed
C–H
activation
and
[4+2]-annulation
S–aryl
sulfoximines
with
vinylene
carbonate.
Notably,
introduction
an
N-protected
amino
acid
ligand
significantly
enhances
reaction
rate.
The
key
aspect
process
is
utilization
carbonate
as
oxidizing
acetylene
surrogate
efficient
transfer
agent.
This
enables
cyclization
sulfoximine
motifs,
successfully
forming
diverse
array
1,2-benzothiazine
derivatives
in
moderate
to
good
yields.
Importantly,
study
highlights
potential
reactions
for
optically
pure
high
enantiomeric
purity.
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
Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(7), P. 1304 - 1309
Published: Feb. 8, 2024
A
Rh(III)-catalyzed
C–H
bond
activation
and
subsequent
[4+1]
annulation
of
benzamides
with
vinyl
cyclic
carbonates
have
been
developed
for
the
synthesis
isoindolinones,
in
which
electron-rich
alkenes
could
serve
as
one-carbon
units.
This
reaction
proceeds
smoothly
high
regioselectivity
under
oxidant-
silver-free
conditions
exhibits
broad
substrate
scope
functional
group
tolerance
including
some
biological
active
materials.
The
scale-up
derivatizations
product
further
demonstrate
potential
synthetic
utility
this
transformation.
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.
The Journal of Organic Chemistry,
Journal Year:
2025,
Volume and Issue:
unknown
Published: April 18, 2025
A
Pd-catalyzed
protocol
that
provides
efficient
access
to
acyclic
1,2-dioxygenated
dienes
has
been
established.
The
installation
of
the
bifunctional
carbonate
electrofuge
diene
cores
enabled
such
undergo
a
regioselective
decarboxylative
Diels-Alder
cycloaddition/aromatization
reaction,
affording
diverse
synthetic
challenging
multisubstituted
phenols
with
ease.
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.
Organic Letters,
Journal Year:
2022,
Volume and Issue:
25(1), P. 109 - 114
Published: Dec. 9, 2022
With
triethylamine
as
a
vinylene
source,
convenient
protocol
for
the
regioselective
synthesis
of
β,γ-nonsubstituted
2-arylquinolines
from
aldehydes
and
arylamines
has
been
accomplished.
The
deaminative
cyclization
is
also
extended
to
long-chain
tertiary
alkylamines,
enabling
diverse
alkyl
groups
be
concurrently
installed
into
pyridine
rings.
This
process
demonstrates
new
conversion
pathway
simultaneous
dual
C(sp3)-H
bond
functionalization
amines,
wherein
transient
acyclic
enamines
generated
in
situ
undergo
Povarov
reaction.
The Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
88(4), P. 2358 - 2366
Published: Feb. 8, 2023
A
novel
protocol
for
the
construction
of
functionalized
1H-pyrrolo[3,4-c]quinoline-1,3(2H)-diones
(PQLs,
3)
from
N-phenylglycines
and
maleimides
was
developed.
The
cascade
reaction
enabled
by
heating
a
mixture
two
substrates
in
presence
di-tert-butyl
peroxide
(DTBP)
as
an
oxidant
anhydrous
CuBr
catalyst
chlorobenzene.
Consequently,
diverse
series
PQLs
3
were
synthesized
moderate-to-good
yields
(43-73%).
synthesis
via
one-pot
that
proceeded
through
subsequent
oxidative
decarboxylation,
1,2-addition,
intramolecular
cyclization,
tautomerization,
aromatization
reactions.
This
can
be
used
decarboxylation
annulation
rather
than
multistep
reactions,
making
it
suitable
both
combinatorial
parallel
syntheses
PQLs.
The Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
88(16), P. 12054 - 12063
Published: July 28, 2023
A
palladium
catalyzed
annulation
of
o-iodo-anilines
with
propargyl
alcohols
for
the
synthesis
substituted
quinolines
has
been
developed.
The
reaction
tolerates
diverse
functional
groups
under
mild
conditions,
providing
direct
access
to
2,4-disubstituted
from
easily
available
starting
materials.
broad
range
were
efficiently
prepared
in
good
excellent
yields.
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.
