The Journal of Organic Chemistry,
Journal Year:
2025,
Volume and Issue:
unknown
Published: April 25, 2025
A
new
combination
of
CuF2/DTBP-catalyzed
N-arylation
oxazolidinones,
amides,
amines,
and
azoles
has
been
explored
with
arylboronic
acid
pinacol
esters
(arylBpin).
This
methodology
also
applied
to
the
synthesis
oxazolidinone-based
marketed
drugs,
including
Rivaroxaban,
Linezolid,
Sutezolid,
Toloxatone.
Mechanistic
investigations
using
various
spectroscopic
techniques
DFT
studies
revealed
role
DTBP/MeOH
in
catalytic
process.
Chemical Science,
Journal Year:
2021,
Volume and Issue:
13(5), P. 1192 - 1209
Published: Dec. 8, 2021
Sulfoxonium
ylides
are
important
surrogates
for
diazo
compounds,
and
their
use
in
industry
as
safer
alternatives
has
been
evaluated
during
recent
years.
Beyond
the
known
classical
transformations,
these
have
also
used
a
surprising
plethora
of
novel
intrinsic
chemical
reactions,
especially
Bench
stability
handling
an
advantage
this
class
organosulfur
molecules.
Despite
this,
efficient
asymmetric
specifically
catalytic
enantioselective
versions,
only
recently
reported,
there
specific
reasons
this.
This
perspective
article
covers
topic
from
first
studies
up
to
latest
advances,
giving
personal
perspectives
showing
main
challenges
area
coming
Organic Chemistry Frontiers,
Journal Year:
2022,
Volume and Issue:
9(16), P. 4388 - 4393
Published: Jan. 1, 2022
The
synthesis
of
3-trifluoromethylisoquinolinones
by
a
ruthenium(
ii
)-catalyzed
C–H
activation/annulation
reaction
benzoic
acids
and
CF
3
-imidoyl
sulfoxonium
ylides
has
been
achieved.
Journal of the American Chemical Society,
Journal Year:
2023,
Volume and Issue:
145(15), P. 8417 - 8429
Published: March 23, 2023
Mechanistic
understanding
of
asymmetric
induction
plays
a
crucial
role
in
designing
new
catalytic
reactions.
Reported
herein
is
atroposelective
access
to
C-N
axially
chiral
isoquinolones
via
rhodium-catalyzed
C-H
activation
N-alkoxy
benzamides
and
annulation
with
imidoyl
sulfoxonium
ylides.
The
coupling
system
proceeded
excellent
functional
group
tolerance,
different
conditions
were
identified
afford
one
or
the
other
enantiomeric
product
each
enantioselectivity
for
representative
class
ylide
reagent,
thus
making
both
enantiomers
readily
available
using
same
catalyst.
Experimental
computational
studies
revealed
pathway
alkylation
enantio-determining
formal
nucleophilic
substitution-C-N
cyclization
that
mediated
by
rhodium
catalyst
σ-bond
metathesis
as
mechanism.
Computational
indicated
solvent-dependent
enatiodivergence
originated
from
levels
neutral
versus
cationic
species.
Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(1), P. 62 - 67
Published: Jan. 3, 2024
We
have
found
a
chameleonic
reactivity
of
imidoyl
sulfoxonium
ylides.
On
the
one
hand,
ylides
react
with
electron-deficient
reagents,
such
as
alkynyl
esters,
to
lead
formation
1,2-dihydro-pyridines.
The
methyl
group
attached
sulfur
atom
acts
methylene
donor.
other
pyridinium
1,4-zwitterionic
thiolates,
which
leads
functionalized
pyrroles.
Both
transformations
feature
mild
reaction
conditions
and
good
functional
tolerance.
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.
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(40), P. 7288 - 7293
Published: Oct. 4, 2022
A
ruthenium-catalyzed
peri-selective
C-H
activation
and
annulation
of
1-naphthols
with
CF3-substituted
imidoyl
sulfoxonium
ylides
that
uses
hydroxyl
as
a
weakly
coordinating
directing
group
is
disclosed.
The
strategy
provides
facile
practical
route
to
diverse
trifluoromethyl-containing
2,3-dihydrobenzo[de]chromen-2-amines
high
efficiency.
Notable
advantages
this
protocol
include
readily
available
materials,
excellent
regioselectivity,
good
functional
compatibility,
scalability.
Organic Letters,
Journal Year:
2022,
Volume and Issue:
24(48), P. 8864 - 8869
Published: Dec. 1, 2022
An
efficient
and
straightforward
approach
for
the
synthesis
of
trifluoromethyl-decorated
benzo[de][1,8]naphthyridines
has
been
achieved
via
Rh(III)-catalyzed
dual
C-H
activation
cascade
annulation
benzimidates
CF3-imidoyl
sulfoxonium
ylides.
The
novel
transformation
involves
formation
four
new
chemical
bonds
along
with
release
two
molecules
dimethyl
sulfoxide
(DMSO)
one
molecule
each
ethanol
amine.
optoelectronic
properties
obtained
fused
aromatic
products
have
investigated
by
recording
UV-vis
absorption
emission
spectra.
Organic Letters,
Journal Year:
2022,
Volume and Issue:
24(37), P. 6822 - 6827
Published: Sept. 9, 2022
A
straightforward
strategy
for
the
metal-free
construction
of
trifluoromethyl-containing
pyrazole
derivatives
has
been
achieved
from
readily
available
α-halo
hydrazones
and
CF3-imidoyl
sulfoxonium
ylides.
The
cascade
transformation
proceeds
through
formal
[4+1]
cycloaddition
followed
by
an
unexpected
dual
double
bond
isomerization.
protocol
features
mild
conditions,
easy
operation,
excellent
substrate
compatibility,
good
regioselectivity.
synthetic
utility
is
demonstrated
scale-up
reaction
further
elaboration
obtained
products.
