Advanced Synthesis & Catalysis,
Год журнала:
2024,
Номер
366(19), С. 4073 - 4077
Опубликована: Июль 3, 2024
Abstract
A
catalyst‐
and
additive‐free
one‐step
protocol
for
synthesizing
thiazolines
thiazolidin‐4‐ones,
utilizing
the
annulative
coupling
between
β‐ketosulfoxonium
ylides
β‐ketothioamides
has
been
described.
The
dual
functionalization
of
through
S‐alkylation
intramolecular
N‐cyclization
leads
to
generation
both
C−S
C−N
bonds.
developed
synthetic
methods
facilitate
synthesis
diverse
functionalized
thiazolidin‐4‐one
derivatives,
validated
large‐scale
reactions.
Organic Letters,
Год журнала:
2024,
Номер
26(25), С. 5263 - 5268
Опубликована: Июнь 14, 2024
A
green
and
sustainable
electrochemical
oxidative
cyclization
of
enaminones
with
thioamides
under
metal-
oxidant-free
conditions
has
been
developed,
providing
an
efficient
approach
for
thiazole
synthesis.
Furthermore,
1,2,4-thiadiazoles
can
be
selectively
accessed
via
the
dimerization
in
absence
enaminones.
Synthesis,
Год журнала:
2024,
Номер
56(16), С. 2565 - 2571
Опубликована: Апрель 26, 2024
Abstract
Visible-light
photocatalytic
reactions
between
enaminones
and
thioureas
leading
to
thiazole
products
have
been
achieved.
The
annulation
process
consists
of
tandem
C–S
C–N
bond
formation
by
running
under
air
atmosphere
at
ambient
temperature.
Broad
substrate
tolerance
the
sustainable
protocol
has
verified
practical
synthesis
divergent
thiazoles
with
both
monocyclic
fused
cyclic
structures.
Herein,
visible-light-induced
annulation
of
benzothioamides
with
sulfoxonium
ylides
to
furnish
thiazole
derivatives
is
developed
under
transition-metal-,
photocatalyst-,
and
oxidant-free
conditions.
This
protocol
exhibits
good
substrate
scope,
affording
the
desired
products
satisfied
yields
in
a
mild
green
manner.
Detailed
mechanistic
studies
suggest
that
benzothioamide
plays
dual
role
this
reaction.
Under
visible-light
irradiation,
excited
benzothioamide,
its
triplet
state,
could
undergo
S
attack
C═S
moiety
ylide
followed
by
dissociation
dimethyl
sulfoxide
H
migration
give
key
adduct.
In
addition,
act
as
an
organocatalyst
facilitate
intramolecular
cyclization
adduct
proton
transfer
steps.
After
dehydration
cyclized
intermediate,
can
be
produced.
The Journal of Organic Chemistry,
Год журнала:
2025,
Номер
90(4), С. 1645 - 1655
Опубликована: Янв. 17, 2025
We
present
a
novel,
metal-
and
additive-free
method
for
the
robust
synthesis
of
dihydrofuran-fused
naphthalenes
coumarins.
This
approach
utilizes
annulative
coupling
sulfoxonium
ylides
with
aldehydes,
naphthols,
or
coumarins
at
ambient
temperature.
The
exhibits
broad
substrate
compatibility,
accommodating
various
functional
groups
on
naphthol
coumarin
derivatives
resulting
in
good
to
high
yields
desired
products.
Additionally,
we
successfully
scaled
up
reactions,
synthesized
were
further
converted
other
valuable
bioactive
molecules,
validating
viability
our
approach.
The Journal of Organic Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Апрель 28, 2025
Here,
we
describe
the
synthesis
of
novel
α-carbonyl-α'-vinyl
sulfoxonium
ylides
under
ambient,
catalyst-free,
and
additive-free
conditions,
demonstrating
broad
substrate
scope
scalability
using
β-ketosulfoxonium
α-ynone-esters.
Furthermore,
these
serve
as
versatile
intermediates
for
highly
substituted
furans
via
Brønsted
acid
(p-TsOH)
catalysis
at
130
°C.
This
approach
offers
key
advantages,
including
wide
compatibility,
divergent
product
formation
from
common
precursors,
gram-scale
feasibility,
good
to
excellent
yields.
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(17), С. 12410 - 12420
Опубликована: Авг. 20, 2024
A
flexible
and
metal-free
synthetic
approach
for
synthesizing
2-benzoyl
quinazolinones
2-aryl
via
molecular
iodine-mediated
annulative
coupling
of
sulfoxonium
ylides
with
2-aminobenzamides
has
been
disclosed.
The
method
demonstrates
remarkable
chemoselectivity
efficiency,
leading
to
high
yields
under
optimized
conditions.
broad
substrate
scope,
scalability,
practical
utility
were
highlighted
through
diverse
applications,
including
gram-scale
reactions
the
synthesis
biologically
significant
compounds
such
as
tryptanthrin
chemo/biosensor
derivative.
Chemical Communications,
Год журнала:
2024,
Номер
unknown
Опубликована: Янв. 1, 2024
A
Brønsted
acid-mediated
insertion
of
thioureas/thioamides
into
sulfoxonium
ylides
to
synthesise
40
thiazoles
(34–95%
yields)
under
mild,
metal-free
conditions
is
described.
Organic & Biomolecular Chemistry,
Год журнала:
2024,
Номер
unknown
Опубликована: Янв. 1, 2024
A
novel
elemental
sulfur-mediated
approach
for
the
synthesis
of
2-acyl
benzothiazoles
and
benzoxazole
derivatives
via
annulative
coupling
sulfoxonium
ylides
with
2-aminobenzenethiol
2-aminophenol
derivatives,
respectively,
is
described.
ACS Sustainable Chemistry & Engineering,
Год журнала:
2024,
Номер
12(44), С. 16297 - 16307
Опубликована: Окт. 21, 2024
We
have
developed
a
singlet
oxygen
(1O2)-mediated
regioselective
thiocyanation
of
terminal
alkynes,
indoles,
pyrrole,
anilines,
and
phenols
using
ammonium
thiocyanate
(NH4SCN)
as
an
SCN
source
under
visible
light
irradiation
at
room
temperature.
The
oxidative
alkynes
forms
α-keto
thiocyanates,
while
regioselectively
form
the
respective
products.
Herein,
(SCN
anion)
undergoes
single
electron
transfer
(SET)
by
transferring
to
•SCN
radical,
which
readily
reacts
with
substrates
Green
chemistry
metrics
Eco-scale
evaluations
signify
that
current
protocol
is
acceptable
green
organic
synthesis
process.
Moreover,
this
method
requires
simple
reaction
setup
uses
inexpensive
NH4SCN
source,
O2
oxidant,
low-energy
light.
Thus,
process
mild,
green,
highly
efficient,
eco-friendly,
environmentally
feasible.
European Journal of Organic Chemistry,
Год журнала:
2023,
Номер
26(46)
Опубликована: Окт. 19, 2023
Abstract
We
herein
report
a
protocol
for
the
α‐thio‐
and
α‐seleno‐cyanation
of
different
cyclic
β‐ketoesters
oxindoles
by
using
NaSCN
or
KSeCN
as
easily
accessible
inorganic
nucleophilic
S(e)CN
sources
under
oxidative
conditions.
Key
to
success
both
transformations
is
use
dibenzoylperoxide
an
oxidant
allowing
coupling
two
inherently
species
operationally
simple
conditions
in
high
yields
with
broad
functional
group
tolerance.
