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 Letters,
Journal Year:
2024,
Volume and Issue:
26(27), P. 5811 - 5816
Published: June 28, 2024
A
practical
strategy
for
the
construction
of
diverse
phosphonyl
and
thiofunctionalized
sulfoxonium
ylides
via
controllable
monofunctionalization
hybrid
I(III)/S(VI)
is
presented.
This
process
allows
efficient
P–H
insertion
under
Cu
catalysis,
enabling
synthesis
ylides,
whereas
reaction
with
sulfur-containing
reagents
including
AgSCF3,
KSC(S)OR,
KSCN
mild
conditions
resulted
in
α-trifluoromethylthiolation,
dithiocarbanation,
thiocyanation
accordingly.
Of
note,
wide
substrate
compatibility
(108
examples),
excellent
efficiency
(up
to
99%
yield),
gram-scale
experiments,
various
product
derivatizations
highlight
synthetic
utility
this
protocol.
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.
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.
Advanced Synthesis & Catalysis,
Journal Year:
2023,
Volume and Issue:
365(24), P. 4672 - 4676
Published: Nov. 10, 2023
Abstract
2‐Iminothiazolidin‐4‐one,
5‐ethylidenethiazolidin‐4‐one,
and
thiazolidine‐4‐thione
are
all
medicinally
relevant
structures.
In
this
work,
a
NaSO
2
CF
3
‐promoted
[2+2+1]
cascade
annulation
reaction
of
‐imidoyl
sulfoxonium
ylides
isothiocyanates
was
reported
to
synthesize
variety
decorated
thiazolidine‐4‐thiones
in
35–91%
yields
with
exclusive
stereoselectivity.
The
gram‐scale
further
chemoselective
S
‐alkylations
demonstrated
the
synthetic
utilities
transformation.
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.
Organic & Biomolecular Chemistry,
Journal Year:
2024,
Volume and Issue:
22(35), P. 7121 - 7127
Published: Jan. 1, 2024
We
introduced,
for
the
first
time,
N
-methoxyamide
directed
proximal
C–H
bond
activation
of
imidazo[1,2-
a
]pyridines
C(sp
2
)–C(sp
)
formation
via
transition
metal
catalysed
approach
to
obtain
C-5
arylated
]pyridines.
Chemistry - An Asian Journal,
Journal Year:
2023,
Volume and Issue:
18(19)
Published: Aug. 24, 2023
Pyrimidoindolones
are
an
important
structural
motif
found
in
many
natural
products
and
essential
to
the
pharmaceutical
agrochemical
industry.
Direct
synthesis
of
3,4-unsubstituted
pyrimidoindolones
is
not
easily
accessible.
Here
we
report
a
rhodium(III)-catalyzed
C-H/N-H
activation
annulation
approach
for
obtaining
from
N-carbamoylindoles
vinylene
carbonate.
The
reaction
occurs
at
room
temperature
does
require
any
external
oxidants.
A
diverse
spectrum
indoles
were
demonstrated
be
viable
substrates
capable
producing
desired
high
yields.
In
addition,
scope
has
been
expanded
include
pyrrole
substrate.
Furthermore,
detailed
mechanistic
studies
have
performed
delineate
working
mode
reaction.
Organic & Biomolecular Chemistry,
Journal Year:
2023,
Volume and Issue:
21(41), P. 8320 - 8328
Published: Jan. 1, 2023
A
rhodium-catalyzed
synthesis
of
phenylacetate
has
been
realized
by
direct
C-H
carboxymethylation
anilines
bearing
removable
directing
groups.
The
reaction
occurred
most
efficiently
in
air,
without
any
external
base
or
oxidant.
This
methodology
is
expected
to
provide
a
facile
and
general
access
various
bioactive
2-amino
aromatic
acetic
acid
derivatives.
Chemistry - An Asian Journal,
Journal Year:
2023,
Volume and Issue:
19(4)
Published: Nov. 29, 2023
Abstract
A
palladium‐catalyzed
reaction
for
intermolecular
selective
C−H
cyclocarbonylation
of
2
‐
iodobiphenyls
is
described.
Intriguingly,
the
vinylene
carbonate
acts
as
a
carbon
monoxide
transfer
agent
to
enable
annulation
reaction.
Moreover,
versatile
synthon,
fluoren‐9‐one
can
be
transformed
into
variety
functionalized
organic
molecules,
such
[1,1′‐biphenyl]‐2‐carboxylic
acid,
1′
H
,3′
‐spiro[fluorene‐9,2′‐perimidine]
and
N
‐tosylhydrazones.
European Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
27(5)
Published: Dec. 20, 2023
Abstract
Arylacetaldehydes
and
its
corresponding
esters
are
fundamental
structural
motifs
widespread
in
natural
products
pharmaceuticals.
Herein,
we
developed
a
ruthenium(II)‐catalyzed
direct
formylmethylation
sequential
dehydrogenative
esterification
of
phthalazinones
by
adopting
vinylene
carbonate
as
C2
synthon
(formylmethyl
equivalent).
The
reaction
is
compatible
with
repertoire
substrates
bearing
both
electron‐donating
electron‐withdrawing
substituents.
Strikingly,
the
obtained
governed
additive
used.
A
number
control
experiments
conducted
to
elucidate
mechanism.
Furthermore,
an
important
highlight
confirmation
possible
intermediates
mass
spectrometry.
