The Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
unknown
Published: Sept. 25, 2024
Carbene-catalyzed
[3
+
3]
annulation
of
enals
and
vinyl
sulfoxonium
ylides
has
been
demonstrated.
This
method
efficiently
synthesizes
a
range
2-sulfenylidene-3-cyclohexen-1-ones
with
high
atom
economy.
Notably,
the
presence
ylide
moiety
in
obtained
products
significantly
enhances
their
potential
for
further
synthetic
transformations.
Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(4), P. 809 - 813
Published: Jan. 23, 2024
Herein,
we
report
the
synthesis
of
2H-chromenes
via
catalyst-controlled
highly
regioselective
[3
+
3]
annulation
vinyl
sulfoxonium
ylides
with
quinones.
Under
boron-catalyzed
conditions,
reaction
between
ylide
and
quinone
resulted
in
formation
2H-chromene-4-carboxylates.
In
contrast,
a
different
mechanistic
pathway
was
observed
when
utilizing
Ru(II)
catalytic
system,
which
led
to
2H-chromene-2-carboxylates
through
furan
intermediate.
JACS Au,
Journal Year:
2024,
Volume and Issue:
4(3), P. 1073 - 1080
Published: March 1, 2024
Herein,
we
report
a
highly
regioselective
[4
+
2]-annulation
of
vinyl
sulfoxonium
ylides
with
ynoates
under
light-mediated
conditions.
The
reaction
proceeds
through
the
new
dienyl
ylide,
which
undergoes
photolysis
blue
light
irradiation
to
give
substituted
naphthalene
scaffolds.
method
presented
here
operates
at
room
temperature
and
does
not
require
addition
an
external
photosensitizer.
in
situ-generated
ylide
absorbs
acts
as
photosensitizer
for
formation
arenes.
synthetic
potential
these
benzannulations
was
further
illustrated
by
various
transformations
scale-up
reaction.
Moreover,
control
experiments
quantum
chemical
calculations
reveal
mechanistic
details
developed
Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(31), P. 6736 - 6741
Published: July 29, 2024
A
visible-light-induced
photoredox
three-component
carbocyclization
reaction
of
1,7-enynes
with
sulfoxonium
ylides
and
water
is
reported.
The
protocol
provides
a
facile
entry
to
structurally
valuable
highly
functionalized
cyclopenta[c]quinoline
scaffolds
in
chemoselective
stereoselective
manner.
Salient
features
this
method
include
redox-neutral
conditions,
no
requirement
base
or
other
additive,
good
functional-group
tolerance.
ACS Catalysis,
Journal Year:
2024,
Volume and Issue:
14(4), P. 2805 - 2815
Published: Feb. 8, 2024
Multicomponent
reactions
that
involve
carbenes
with
nucleophiles
and
electrophiles
have
demonstrated
broad
applications
in
synthetic
chemistry.
However,
because
of
the
high
reactivity
transient
carbenes,
involving
two
carbene
precursors
nucleophile
presence
a
metal
catalyst
remain
unexplored.
Herein,
three-component
stereoselective
gem-difunctionalization
diazo
compounds
thiols
vinyl
sulfoxonium
ylide
is
disclosed
via
Co(II)-based
metalloradical
catalysis.
The
key
aspect
present
strategy
to
exploit
intrinsic
difference
ylides
thiol
catalysts.
Doyle–Kirmse
rearrangement
sulfonium
involves
convergent
assembly
situ-generated
intermediates,
such
as
allyl
sulfide
α-
metalloalkyl
radical
complex,
provide
expeditious
access
tertiary
scaffolds.
Combined
experimental
quantum
chemical
calculations
unveil
intricate
mechanism
this
reaction.
Furthermore,
theoretical
studies
on
noncovalent
interactions
selectivity-determining
transition
states
explain
origin
experimentally
obtained
diastereoselectivity.
Organic Letters,
Journal Year:
2023,
Volume and Issue:
25(50), P. 8992 - 8996
Published: Dec. 12, 2023
Herein,
we
report
the
divergent
benzannulation
for
highly
substituted
arenes
using
vinyl
sulfoxonium
ylides
and
ynones.
The
addition
of
ynone
at
γ-position
leads
to
dienyl
ylide
that
can
undergo
selective
annulation
under
different
conditions
give
m-terphenyls
parabens.
Moreover,
control
experiments
quantum
chemical
calculations
reveal
two
distinct
reaction
mechanisms
both
annulations.
Chemical Communications,
Journal Year:
2024,
Volume and Issue:
60(28), P. 3846 - 3849
Published: Jan. 1, 2024
The
coupling
of
ylide-derived
carbene
with
diazo-derived
generated
dienoates
via
cascade
catalysis.
Similarly,
the
reaction
oxocarbenium
ion
afforded
alkylidenebutenolide
synergistic
Organic Letters,
Journal Year:
2023,
Volume and Issue:
25(43), P. 7906 - 7910
Published: Oct. 24, 2023
Herein,
we
report
the
synthesis
of
π-conjugation-extended
vinyl
sulfoxonium
ylides
from
ylide
and
electron-deficient
alkynes.
The
new
dienoate
are
used
in
various
transformations,
such
as
X-H
(X
=
S,
O)
insertion,
halogenation,
carbene-mediated
transformation,
radical-mediated
reductions
to
obtain
a
variety
conjugated
dienoates.
The Journal of Organic Chemistry,
Journal Year:
2025,
Volume and Issue:
unknown
Published: Feb. 2, 2025
A
mild
and
efficient
protocol
for
the
perhaloacylation
of
α-carbonyl
sulfoxonium
ylides
has
been
developed.
The
commercially
available
perfluoro-
perchloroacid
anhydrides
were
used
as
acylating
agents
in
catalyst-
additive-free
reactions
to
access
α-carbonyl-α'-perhaloacyl
high
yields.
reaction
offers
a
simple
method
prepare
valuable
polyfluorinated
organosulfur
molecules.
Organic Letters,
Journal Year:
2025,
Volume and Issue:
unknown
Published: Feb. 15, 2025
We
report
an
unusual
ring
contraction
of
4-chlorocoumarin
to
benzofuranoyl
sulfoxonium
ylides
using
a
Corey-ylide.
These
stabilized
were
subsequently
utilized
for
the
synthesis
various
valuable
bis-heterocycles
under
both
metal
and
metal-free
conditions.
The
synthetic
utility
this
method
is
illustrated
through
known
bioactive
compounds.
Detailed
mechanistic
investigations
quantum
chemical
calculations
have
provided
insights
into
mechanism
reaction.