Molecules,
Год журнала:
2023,
Номер
28(13), С. 5014 - 5014
Опубликована: Июнь 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.
Angewandte Chemie International Edition,
Год журнала:
2022,
Номер
61(41)
Опубликована: Авг. 24, 2022
Exploring
new
routes
to
lock
the
dynamic
C=N
bonds
in
imine-linked
covalent
organic
frameworks
(COFs)
is
highly
desired
for
enhancing
their
stability
and
functionality.
Herein,
a
novel
bridge
locking
strategy
via
rhodium-catalyzed
[4+2]
annulation
developed
construct
nonsubstituted
quinoline-linked
COFs
(NQ-COFs).
The
notable
feature
of
this
includes
high
conversion
efficiency,
oxidant-free,
generality
synthesis
variety
NQ-COFs
with
chemical
stability.
Particularly,
after
post-synthetic
modification,
crystallinity,
topology,
porosity
pristine
are
well
retained.
When
used
as
photocatalysts,
display
better
visible
light
absorption
carriers'
separation
efficiency
due
enhanced
in-plane
π
conjugation
ability,
more
facile
generation
superoxide
anion
radicals
than
counterparts,
thus
leading
efficient
2,4,6-tris(aryl)pyridines,
benzimidazole,
sulfoxide
derivatives.
Organic Letters,
Год журнала:
2022,
Номер
24(5), С. 1146 - 1151
Опубликована: Фев. 3, 2022
A
novel
photo-thermo-mechanochemical
approach
to
assembling
quinolines
catalyzed
by
iron(II)
phthalocyanine
has
been
realized
for
the
first
time.
This
transformation
features
a
cost-efficient
catalytic
system
and
operational
simplicity,
is
free
of
solvent,
shows
good
substrate
tolerance,
providing
green
alternative
existing
thermal
approaches.
Mechanistic
experiments
demonstrate
that
in-situ-formed
secondary
amine
may
be
key
intermediate
further
cyclization/aromatization
process.
Organic Letters,
Год журнала:
2022,
Номер
24(14), С. 2613 - 2618
Опубликована: Апрель 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,
Год журнала:
2022,
Номер
24(31), С. 5679 - 5683
Опубликована: Июль 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,
Год журнала:
2022,
Номер
58(28), С. 4476 - 4479
Опубликована: Янв. 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
Organic Chemistry Frontiers,
Год журнала:
2023,
Номер
10(22), С. 5717 - 5734
Опубликована: Янв. 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,
Год журнала:
2023,
Номер
365(9), С. 1457 - 1464
Опубликована: Апрель 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
The Journal of Organic Chemistry,
Год журнала:
2023,
Номер
88(5), С. 2952 - 2960
Опубликована: Фев. 20, 2023
A
metal-free
method
for
the
construction
of
2-substituted
quinolines
and
benzo[f]quinolines
from
aromatic
amines,
aldehydes,
tertiary
amines
has
been
demonstrated.
Cheap
readily
available
acted
as
vinyl
source.
new
pyridine
ring
was
selectively
formed
via
[4
+
2]
condensation
that
promoted
by
ammonium
salt
under
neutral
conditions
an
oxygen
atmosphere.
This
strategy
provided
a
route
preparation
various
quinoline
derivatives
with
different
substituents
at
ring,
which
provides
possibility
further
modification.
Green Chemistry,
Год журнала:
2023,
Номер
25(11), С. 4282 - 4291
Опубликована: Янв. 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,
Год журнала:
2023,
Номер
365(20), С. 3400 - 3412
Опубликована: Сен. 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.
