Molecules,
Год журнала:
2025,
Номер
30(3), С. 655 - 655
Опубликована: Фев. 1, 2025
This
review
probes
the
recent
developments
in
stereoselective
reactions
within
area
of
sulfoxonium
ylide
chemistry
since
early
2000s.
An
abundance
research
has
been
applied
to
its
emergence
1960s.
There
a
continued
effort
then
with
work
traditional
areas,
such
as
epoxidation,
aziridination
and
cyclopropanation.
Efforts
have
also
novel
olefination
insertion
reactions,
develop
methodologies
using
organocatalysis
transition
metal
catalysis.
The
growing
interrupted
Johnson–Corey–Chaykovsky
is
described,
whereby
unexpected
cyclopropanation
epoxidation
developed.
In
general,
most
observed
mechanistic
pathway
ylides
formal
cycloaddition:
(2
+
1)
(e.g.,
epoxides,
cyclopropanes,
aziridines),
(3
oxetanes,
azetidines),
(4
indanones,
indolines).
involves
formation
zwitterionic
intermediate
through
nucleophilic
addition
carbanion
an
electrophilic
site.
intramolecular
cyclization
occurs,
constructing
cyclic
product.
Insertion
X–H
bonds
X
=
S,
N
or
P)
are
observed,
protonation
followed
by
X,
form
inserted
Organic Letters,
Год журнала:
2023,
Номер
25(7), С. 1214 - 1217
Опубликована: Фев. 9, 2023
An
efficient
catalyst-
and
additive-free
facile
synthesis
of
α-carbonyl-α′-amide
sulfoxonium
ylides
from
isocyanates
β-ketosulfoxonium
with
complete
atom
economy
has
been
described.
The
adorned
various
functional
groups
were
well-tolerated
afforded
moderate
to
high
yields
the
ylide
derivatives.
Finally,
using
large-scale
reactions
converting
synthesized
into
other
valuable
compounds,
we
demonstrated
practicality
this
synthetic
method.
Organic Letters,
Год журнала:
2024,
Номер
26(27), С. 5811 - 5816
Опубликована: Июнь 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 Letters,
Год журнала:
2018,
Номер
21(1), С. 296 - 299
Опубликована: Дек. 20, 2018
The
lack
of
general
access
to
bis-substituted
sulfoxonium
ylides
is
addressed
by
developing
a
palladium-catalyzed
C–H
cross-coupling
α-ester
with
(hetero)aryl
iodides,
bromides,
and
triflates.
Three
different
catalysts
have
been
evaluated.
This
method
amenable
the
late-stage
functionalization
active
pharmaceutical
ingredients.
Organic Letters,
Год журнала:
2019,
Номер
21(4), С. 1125 - 1129
Опубликована: Фев. 4, 2019
The
first
iridium-catalyzed
three-component
coupling
reaction
of
carbon
dioxide,
amines,
and
sulfoxonium
ylides
has
been
developed,
providing
an
efficient
straightforward
method
for
the
construction
a
range
structurally
diverse
O-β-oxoalkyl
carbamates
in
moderate
to
excellent
yields.
This
novel
protocol
features
use
readily
available
substrates,
wide
substrate
scope,
good
functional
group
tolerance.
Moreover,
phosgene-free
strategy
was
successfully
applied
synthesis
potential
antitumor
agent.
The Journal of Organic Chemistry,
Год журнала:
2020,
Номер
85(11), С. 7433 - 7445
Опубликована: Апрель 28, 2020
Imidoyl
sulfoxonium
ylides
are
presented
for
the
first
time
as
potential
precursors
to
generate
α-imino
metal-carbene
intermediates
and
applied
in
direct
C-H
functionalization
reactions
catalyzed
by
[Ir(cod)Cl]2
(4
mol
%)
provide
2-substituted
indoles
(up
70%
yield)
just
one
step.
This
class
of
sulfur
ylide
is
successfully
obtained
from
imidoyl
chloride
dimethylsulfoxonium
methylide
(23
new
examples
45-85%
or
imino
group
formation
corresponding
β-keto
anilines
presence
TiCl4
a
Lewis
acid
(9
33-94%
yield).
Organic Letters,
Год журнала:
2019,
Номер
21(13), С. 5310 - 5314
Опубликована: Июнь 26, 2019
The
synthesis
of
1,1-dicarbonyl
sulfoxonium
ylides
by
palladium-catalyzed
carbonylation
aryl
halides
or
triflates
with
α-carbonyl
has
been
developed
for
the
first
time.
This
method
provides
a
general
approach
to
synthetically
useful
in
high
efficiency.
protocol
displays
wide
substrate
scope,
showing
that
resulting
have
converted
into
corresponding
1,3-dicarbonyl
compounds.
Chinese Journal of Chemistry,
Год журнала:
2021,
Номер
39(6), С. 1646 - 1650
Опубликована: Фев. 26, 2021
Main
observation
and
conclusion
A
visible
light‐promoted
reaction
of
donor/acceptor
diazoalkanes
with
sulfoxides
towards
the
synthesis
synthetically
useful
sulfoxonium
ylides
was
reported.
The
occurred
under
sole
light
irradiation
without
need
any
transition‐metals
or
additives,
affording
corresponding
in
moderate
to
good
yields.
success
late‐stage
modification
natural
isolates
drug
candidates,
scale‐up
transformation
other
molecules
further
rendered
approach
valuable.
Organic & Biomolecular Chemistry,
Год журнала:
2021,
Номер
19(26), С. 5767 - 5771
Опубликована: Янв. 1, 2021
A
copper-catalyzed
P–H
insertion
reaction
between
sulfoxonium
ylides
and
H-phosphorus
oxides
has
been
developed
to
synthesize
α-phosphonyl
carboxylate
derivatives.
Organic Letters,
Год журнала:
2023,
Номер
25(28), С. 5329 - 5332
Опубликована: Июль 7, 2023
A
novel
straightforward
and
catalyst-free
approach
for
synthesizing
quinoxaline
derivatives
from
sulfoxonium
ylides
o-phenylenediamines
mediated
by
elemental
sulfur
has
been
described.
Due
to
the
simple
mild
reaction
conditions,
decorated
with
different
functional
groups
furnished
moderate
high
yields
of
were
well
tolerated.
Finally,
large-scale
reactions,
synthesis
pyrazines,
some
bioactive
compounds
are
used
illustrate
potential
utility
developed
approach.
Organic Chemistry Frontiers,
Год журнала:
2021,
Номер
8(5), С. 988 - 995
Опубликована: Янв. 1, 2021
A
general
and
practical
strategy
for
the
construction
of
various
keto-substituted
isoxazolidines
via
one-pot
three-component
reaction
easily
accessible,
safer
more
stable
sulfoxonium
ylides,
nitrosoarenes
olefins
is
described.
