Advanced Synthesis & Catalysis,
Journal Year:
2021,
Volume and Issue:
363(13), P. 3311 - 3317
Published: May 8, 2021
Abstract
A
method
to
synthesize
pyrazolo[1,2‐a]cinnolines
via
rhodium(III)‐catalyzed
C−H
activation
of
pyrazolidinones
and
subsequent
[4+2]
annulation
sulfoxonium
ylides
was
developed.
5‐Substituted
or
5,10‐disubstituted
could
be
obtained
by
slightly
adjusting
the
reaction
conditions.
Gram‐scale
synthesis
practical
transformations
proved
practicability
this
method.
The
mechanism
proposed
in
article
on
basis
preliminary
mechanistic
results
previous
reports.
This
features
simplified
operation,
metal‐oxidant
free,
readily
available
reactants.
magnified
image
Organic & Biomolecular Chemistry,
Journal Year:
2020,
Volume and Issue:
18(43), P. 8793 - 8809
Published: Jan. 1, 2020
Sulfur
ylides
first
disclosed
in
1930
started
to
gain
more
attention
the
1960s,
thanks
mainly
studies
by
Corey
and
Chaykovsky
on
their
use
for
preparation
of
strained
rings.
More
recently,
chemistry
these
compounds
has
experienced
important
growth,
part
due
similarity
reactivities
with
diazo
compounds.
This
short
review
provides
an
overview
great
assortment
reactions
sulfoxonium
ylides,
outlining
a
comparison
between
congeners:
sulfonium
Insertion
reactions,
cyclisation
ring-opening
are
highlighted,
giving
particular
catalytic
asymmetric
methodologies.
Asian Journal of Organic Chemistry,
Journal Year:
2022,
Volume and Issue:
11(4)
Published: March 23, 2022
Abstract
In
recent
years,
the
transition‐metal‐catalyzed
functionalization
reactions
of
sulfoxonium
ylides
have
been
explored
extensively
because
their
usefulness
as
carbene‐transfer
agents,
since
they
can
produce
metal
carbenes
through
catalysis.
Moreover,
are
safer
and
advantages
simple
handling
good
stability
over
other
counterparts
like
diazo‐compounds.
This
review
article
attempts
to
highlight
advances
in
metal‐catalyzed
C−H
ylides.
The Journal of Organic Chemistry,
Journal Year:
2020,
Volume and Issue:
85(5), P. 3192 - 3201
Published: Jan. 16, 2020
We
report
the
synthesis
of
C6-substituted
isoquinolino[1,2-b]quinazolinones
via
rhodium(III)-catalyzed
C–H
annulation
with
sulfoxonium
ylides
and
evaluation
cytotoxic
activity
scaffold.
This
activation
approach
enables
most
straightforward
convergent
isoquinolino[1,2-b]quinazolines
reported
to
date.
operationally
simple
method
is
compatible
a
wide
variety
ylide
arene
coupling
partners,
permitting
access
diverse
isoquinolino[1,2-b]quinazolines.
shows
high
atom
economy,
generating
H2O
dimethyl
sulfoxide
(DMSO)
as
by-products.
scalable
operates
exquisite
N-lactam
cyclization
selectivity,
thus
enabling
expedient
new
heterocyclic
analogues
featuring
promising
properties.
Organic Letters,
Journal Year:
2020,
Volume and Issue:
22(12), P. 4806 - 4811
Published: June 1, 2020
Site-selective
direct
functionalization
of
an
indole
benzenoid
core
has
been
a
great
challenge
due
to
its
inherently
poor
reactivity.
We
herein
demonstrate
iridium-catalyzed
C4-selective
acylmethylation
indoles
using
α-carbonyl
sulfoxonium
ylides
as
carbene
precursors.
This
method
exhibits
high
efficiency
and
broad
functional
group
compatibility.
The
directing
was
easily
removed
or
converted
other
functionalities
after
the
catalysis.
potential
synthetic
utility
coupling
products
highlighted
by
constructing
medium-sized
polycyclic
indoles.
Organic Letters,
Journal Year:
2020,
Volume and Issue:
22(4), P. 1375 - 1379
Published: Feb. 3, 2020
The
synthesis
of
indanone
derivatives
by
the
Rh(III)-catalyzed
reaction
α-carbonyl
sulfoxonium
ylides
with
activated
alkenes
is
reported.
shows
a
high
tolerance
for
functional
groups
and
furnishes
variety
substituted
via
formal
[4
+
1]
cycloaddition.
Highly
stable
were
used
as
substrates
in
this
C-H
functionalization,
their
bifunctional
character
could
be
effectively
exploited
using
Rh(III)
catalysis
sequential
double
C-C
bond
formation.
Based
on
mechanistic
studies
including
deuterium-labeling
experiments,
proposed
to
proceed
follows:
oxidative
alkenylation
β-hydride
elimination,
readdition
H-Rh
species,
1,2-carbon
shift
elimination
DMSO,
protonation.
Organic Letters,
Journal Year:
2021,
Volume and Issue:
23(3), P. 1038 - 1043
Published: Jan. 21, 2021
A
ruthenium-catalyzed
highly
chemoselective
N-alkylation
of
2-pyridones
has
been
developed,
affording
N-alkylated
2-pyridone
derivatives
in
good
yields
and
excellent
N-selectivity.
The
key
to
achieve
this
unprecedented
N–H
rather
than
O–H
insertion
reaction
is
the
use
CpRu(PPh3)2Cl
as
catalyst
sulfoxonium
ylides
alkylation
reagents.
Moreover,
protocol
also
amenable
7-azaindoles
by
slightly
varying
conditions.
Furthermore,
sulfonium
are
suitable
reagents,
providing
selectivity.
Organic & Biomolecular Chemistry,
Journal Year:
2021,
Volume and Issue:
19(8), P. 1705 - 1721
Published: Jan. 1, 2021
A
review
highlighting
the
advances
in
Cp*Rh(iii)
catalysed
cascade
arene
C–H
activation/annulation
including
application,
scope,
limitations
and
mechanism
of
these
transformations.
The Journal of Organic Chemistry,
Journal Year:
2021,
Volume and Issue:
87(2), P. 1124 - 1132
Published: Dec. 29, 2021
An
efficient
and
practical
strategy
was
developed
to
synthesize
1,3,4-triaryl-6-trifluoromethylpyridones
from
CF3-imidoyl
sulfoxonium
ylides
cyclopropenones
in
good
excellent
yields.
This
stepwise
[3
+
3]
annulation
reaction
carried
out
under
transition-metal-,
additive-,
solvent-free
conditions,
generating
1
equiv
of
dimethyl
sulfoxide
as
byproduct
tolerating
a
series
functional
groups.
Organic Letters,
Journal Year:
2022,
Volume and Issue:
24(43), P. 8062 - 8066
Published: Oct. 24, 2022
An
efficient
base,
additive
and
metal-free
synthetic
methods
for
α-ketothioamide
α-ketoamide
derivatives
from
readily
available
sulfoxonium
ylides
have
been
described.
Sulfoxonium
with
primary
or
secondary
amines
afforded
α-ketothioamides
in
the
presence
of
elemental
sulfur,
whereas
α-ketoamides
were
produced
when
I2
TBHP
present.
The
reaction
proceeded
well
at
room
temperature
generated
corresponding
molecules
good
to
excellent
yields.
can
be
scaled-up
tolerated
by
a
range
functional
groups
simple
operational
procedures.
