Organic Letters,
Journal Year:
2021,
Volume and Issue:
23(7), P. 2836 - 2840
Published: March 19, 2021
A
three-component
method
is
described
for
the
preparation
of
syn-1,2-disubstituted
bridged
bicyclic
compounds.
The
reaction
was
demonstrated
readily
available
aromatic
and
heteroaromatic
C–H
bond
substrates
with
tertiary
secondary
amide,
lactam,
pyrazole,
triazole
directing
groups
a
variety
alkenes,
including
norbornene,
benzonorbornadiene,
oxygen-
nitrogen-bridged
analogs,
an
unsaturated
tropinone.
broad
dioxazolone
scope
also
observed.
use
chiral
Cp-derived
RhIII
catalyst
enables
asymmetric
synthesis
products.
Organic & Biomolecular Chemistry,
Journal Year:
2022,
Volume and Issue:
20(5), P. 1112 - 1116
Published: Jan. 1, 2022
The
direct
synthesis
of
isocoumarin
skeletons
has
been
realized
through
the
Rh(
iii
)-catalyzed
[3
+
3]
annulation
sulfoxonium
ylides
and
iodonium
under
mild
conditions.
Organic Letters,
Journal Year:
2022,
Volume and Issue:
24(5), P. 1146 - 1151
Published: Feb. 3, 2022
A
novel
photo-thermo-mechanochemical
approach
to
assembling
quinolines
catalyzed
by
iron(II)
phthalocyanine
has
been
realized
for
the
first
time.
This
transformation
features
a
cost-efficient
catalytic
system
and
operational
simplicity,
is
free
of
solvent,
shows
good
substrate
tolerance,
providing
green
alternative
existing
thermal
approaches.
Mechanistic
experiments
demonstrate
that
in-situ-formed
secondary
amine
may
be
key
intermediate
further
cyclization/aromatization
process.
Advanced Synthesis & Catalysis,
Journal Year:
2021,
Volume and Issue:
363(5), P. 1436 - 1442
Published: Jan. 21, 2021
Abstract
A
highly
efficient
cascade
Rh(III)‐catalyzed
C−H
activation/intramolecular
chemodivergent
cyclization
reaction
of
N‐carbamoylindoles
and
sulfoxonium
ylides
has
been
successfully
achieved
for
the
first
time.
This
synergistic
process
provides
rapid
access
to
functionalized
dihydropyrimidoindolone
tricyclic
[1,3]oxazino[3,4‐
a
]indol‐1‐ones
skeletons
under
redox
neutral
conditions
with
broad
substrate
scope
remarkable
functional‐group
compatibility.
Further
late‐stage
modification
structurally
complex
drug
molecules
mechanistic
studies
were
also
accomplished.
magnified
image
Advanced Synthesis & Catalysis,
Journal Year:
2023,
Volume and Issue:
365(9), P. 1457 - 1464
Published: April 14, 2023
Abstract
In
this
study,
Rh(III)‐catalyzed
C−H
bifunctionalization
and
direct
vinylene
annulation
of
sulfoxonium
ylides
N
‐carbamoylindoles
with
carbonate
was
accomplished,
which
afforded
a
series
naphthalenones
containing
β‐ketosulfoxonium
ylide
moiety,
isocoumarins,
pyrimidones.
This
protocol
featured
mild
conditions,
broad
substrate
scope,
functional‐groups
compatibility.
addition,
related
applications
preliminary
mechanistic
exploratory
were
also
investigated
magnified
image
Chinese Journal of Chemistry,
Journal Year:
2021,
Volume and Issue:
39(9), P. 2489 - 2494
Published: May 9, 2021
Main
observation
and
conclusion
Divergent
synthesis
of
useful
skeletons
has
been
realized
via
rhodium(III)‐catalyzed
C—H
activation
iminopyridinium
ylides
coupling
with
various
unsaturated
reagents.
Isocoumarins
isoquinolones
were
obtained
cleavage
the
C—N
or
N—N
bond
in
ylidic
directing
group,
while
fluorinated
alkenes
delivered
group
intact.
The
reactions
occurred
wide
substrate
scopes
good
efficiency
under
redox‐neutral
air‐tolerant
conditions.
Representative
products
exhibit
solid‐state
fluorescent
property
bioactivity
inhibition
toward
human
cancer
cells.
The Journal of Organic Chemistry,
Journal Year:
2022,
Volume and Issue:
87(6), P. 4134 - 4153
Published: March 4, 2022
Air-stable,
highly
abundant,
and
cost-effective
Co(III)-catalyzed
redox-neutral
[4
+
2]-annulation
of
aromatic
sulfoxonium
ylides
with
1,3-diynes
providing
useful
substituted
1-naphthol
derivatives
in
a
regioselective
manner
is
described.
Further,
the
prepared
1-naphthols
having
internal
alkyne
were
converted
into
polycarbocyclic
molecules
spiro-dienone
good-to-excellent
yields.
A
possible
reaction
mechanism
involving
ortho
C–H
activation
as
key
step
was
proposed
supported
by
deuterium
labeling
kinetic
isotope
studies.
Organic & Biomolecular Chemistry,
Journal Year:
2022,
Volume and Issue:
21(5), P. 879 - 909
Published: Dec. 6, 2022
Transition
metal-catalyzed
cross-coupling
of
sp2
C-H
bonds
with
diazo
compounds
via
carbene
migratory
insertion
represents
an
efficient
strategy
for
the
construction
C-C
and
C-heteroatom
in
organic
synthesis.
Despite
popularity
as
coupling
partners
activation,
they
pose
serious
safety
stability
issues
due
to
potential
exothermic
reactions
linked
release
N2
gas.
However,
compared
compounds,
sulfoxonium
ylides
are
generally
crystalline
solids,
more
stable,
widely
used
industrial
scales,
easier/safer
prepare.
Therefore,
recent
years
have
witnessed
upsurge
employing
α-carbonyl
alternative
surrogate
transition
activation.
Unlike
contain
inherent
serve
a
partner
well
weak
directing
group.
This
review
will
summarize
progress
made
both
categories
reactions.
Nature Communications,
Journal Year:
2022,
Volume and Issue:
13(1)
Published: Nov. 3, 2022
The
development
of
novel
methodologies
for
the
introduction
sulfoxonium
group
under
mild
conditions
is
appealing
but
remains
underexplored.
Herein
we
report
synthesis
a
class
hypervalent
iodine
reagents
with
transferrable
group.
These
compounds
enable
mixed
iodonium-sulfoxonium
ylide
reactivity.
well-defined
are
examined
in
visible-light-promoted
cyclization
reactions
wide
range
unsaturated
bonds
including
alkenes,
alkynes,
nitriles,
and
allenes.
Two
distinct
pathways
identified,
which
controlled
by
substituent
bond.
cycloaddition
protocol
features
simple
operation,
reaction
conditions,
excellent
functional
tolerance,
affording
broad
sulfoxonium-containing
cyclic
structures
moderate
to
yields.
Furthermore,
sufoxonium
product
can
be
transformed
into
diverse
groups
structural
motifs
via
single
electron
transfer
transition-metal
catalysis.
Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(32), P. 6830 - 6834
Published: Aug. 5, 2024
A
ruthenium-catalyzed
C-H
activation
and
a
concomitant
[4+2]
annulation
of
sulfoxonium
ylide
with
maleimide
have
been
demonstrated.
This
tandem
reaction
results
in
the
formation
fused
benzo[
