Asian Journal of Chemistry,
Journal Year:
2024,
Volume and Issue:
36(6), P. 1423 - 1428
Published: May 31, 2024
An
inexpensive
iron-catalyzed
annulation
of
2-aminobenzaldehydes
with
iodonium
ylides
for
the
synthesis
acridinone
derivatives
was
reported.
A
library
biologically
relevant
3,4-dihydropyridine-1-one
scaffold
synthesized
by
reaction
corresponding
2-amino
benzaldehyde
and
under
mild
conditions
in
a
green
solvent.
The
tolerates
various
alkyl,
aryl
halogenated
substrates
affords
desired
product
moderate
to
good
yields.
reported
has
an
catalytic
system,
conditions,
easily
accessible
use
solvents.
Chemical Reviews,
Journal Year:
2024,
Volume and Issue:
unknown
Published: Sept. 13, 2024
Hypervalent
iodine(III)
compounds
have
found
wide
application
in
modern
organic
chemistry
as
environmentally
friendly
reagents
and
catalysts.
iodine
are
commonly
used
synthetically
important
halogenations,
oxidations,
aminations,
heterocyclizations,
various
oxidative
functionalizations
of
substrates.
Iodonium
salts
arylating
reagents,
while
iodonium
ylides
imides
excellent
carbene
nitrene
precursors.
Various
derivatives
benziodoxoles,
such
azidobenziodoxoles,
trifluoromethylbenziodoxoles,
alkynylbenziodoxoles,
alkenylbenziodoxoles
group
transfer
the
presence
transition
metal
catalysts,
under
metal-free
conditions,
or
using
photocatalysts
photoirradiation
conditions.
Development
hypervalent
catalytic
systems
discovery
highly
enantioselective
reactions
chiral
represent
a
particularly
recent
achievement
field
chemistry.
Chemical
transformations
promoted
by
many
cases
unique
cannot
be
performed
any
other
common,
non-iodine-based
reagent.
This
review
covers
literature
published
mainly
last
7-8
years,
between
2016
2024.
Organic Letters,
Journal Year:
2023,
Volume and Issue:
25(24), P. 4422 - 4428
Published: June 8, 2023
Presented
herein
is
a
condition-controlled
selective
synthesis
of
pyranone-tethered
indazoles
or
carbazole
derivatives
via
the
cascade
reactions
N-nitrosoanilines
with
iodonium
ylides.
Mechanistically,
formation
former
involves
an
unprecedented
process
including
nitroso
group-directed
C(sp2)–H
bond
alkylation
N-nitrosoaniline
ylide
followed
by
intramolecular
C-nucleophilic
addition
to
moiety,
solvent-assisted
cyclohexanedione
ring
opening,
and
transesterification/annulation.
On
contrary,
latter
initial
annulation
denitrosation.
These
developed
protocols
feature
easily
controllable
selectivity,
mild
reaction
conditions,
clean
sustainable
oxidant
(air),
valuable
products
that
are
structurally
diverse.
In
addition,
utility
was
showcased
their
facile
diverse
transformations
into
synthetically
biologically
interesting
compounds.
Advanced Synthesis & Catalysis,
Journal Year:
2023,
Volume and Issue:
365(11), P. 1817 - 1823
Published: Feb. 7, 2023
Abstract
We
described
an
Rhodium(III)‐catalyzed
divergent
C−H
bond
functionalization
of
N
‐aryl
amidines
with
iodonium
ylides.
Carbazolones
and
zwitterionic
salts
were
diversely
constructed
through
intermolecular
annulation
intramolecular
proton
transfer
under
the
different
reaction
conditions.
This
protocol
is
operationally
simple
tolerates
a
variety
functional
groups.
The
efficient
post‐modification
pharmaceutical
molecules
demonstrates
its
practicability.
The Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
88(9), P. 5348 - 5358
Published: April 3, 2023
A
facile
access
to
isocoumarins
has
been
established
via
rhodium(III)-catalyzed
C-H
bond
activation
and
intramolecular
C-C
cascade
annulation
of
enaminones
cyclic
1,3-dicarbonyl
compounds.
The
synthetic
protocol
features
a
wide
range
substrates
with
high
functional
group
tolerance,
mild
reaction
conditions,
the
selective
cleavage
enaminone
bond.
Notably,
compounds
can
in
situ-generate
iodonium
ylide
as
carbene
precursor
prepare
polycyclic
scaffolds
by
reacting
PhI(OAc)2.
application
this
method
useful
precursors
bioactive
skeletons
is
also
exemplified.
Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(24), P. 5136 - 5140
Published: June 7, 2024
Herein,
we
report
a
rhodium-catalyzed
C–H
activation/[4+2]
cyclization
reaction
between
α,β-unsaturated
amides
and
iodonium
ylides
for
the
synthesis
of
novel
7,8-dihydroquinoline-2,5-diones
analogues.
This
protocol
provides
series
pyridones
fused
with
saturated
cycles
good
functional
group
compatibility,
water
air
tolerance,
to
excellent
yields
under
mild
green
conditions.
Additionally,
scale-up
can
be
smoothly
performed
as
low
0.25
mol
%
catalyst
loading.
Recycling
experiments
different
transformation
were
also
carried
out
demonstrate
potential
synthetic
utility
this
protocol.
Organic & Biomolecular Chemistry,
Journal Year:
2022,
Volume and Issue:
21(1), P. 24 - 38
Published: Nov. 23, 2022
The
metal-catalyzed
successive
activation
and
functionalization
of
arene/heteroarene
is
one
the
most
fundamental
transformations
in
organic
synthesis
leads
to
privileged
scaffolds
natural
products,
pharmaceuticals,
agrochemicals,
fine
chemicals.
Particularly,
transition-metal-catalyzed
C-H
arenes
with
carbene
precursors
via
metal
migratory
insertion
has
been
well
studied.
As
a
result,
diverse
have
evaluated,
such
as
diazo
compounds,
sulfoxonium
ylides,
triazoles,
etc.
In
addition,
there
significant
developments
use
iodonium
ylides
recent
years,
these
reactions
proceed
high
efficiencies
selectivities.
This
review
provides
comprehensive
overview
functionalizations,
including
scope,
limitations,
their
potential
synthetic
applications.
Advanced Synthesis & Catalysis,
Journal Year:
2024,
Volume and Issue:
366(8), P. 1744 - 1750
Published: Feb. 22, 2024
Abstract
The
transmetalation
triggered
rhodium‐catalyzed
C−H
bond
activation
and
tandem
annulation
of
2‐biphenylboronic
acids
with
sulfoxonium
ylides
or
iodonium
has
been
developed.
Various
products
phenanthrenes
were
constructed
under
redox‐neutral
conditions
in
34–86%
yields.
Several
mechanism
exploration
experiments
derivatization
reactions
conducted
sequence
to
gain
a
deeper
understanding
the
process
potential
this
transformation.
It
offers
an
alternative
approach
for
synthesis
phenanthrene
derivatives.
European Journal of Organic Chemistry,
Journal Year:
2025,
Volume and Issue:
unknown
Published: Feb. 21, 2025
Abstract
Nitrogen‐containing
heterocyclic
compounds
are
the
core
skeletons
of
many
natural
products,
bioactive
molecules
and
drugs,
transition
metal‐catalyzed
hydrazine‐directed
C−H
bond
activation/annulation
reactions
is
one
effective
methods
for
synthesis
nitrogen‐containing
compounds.
In
this
review,
important
research
progress
activation
reviewed
according
to
size
constructed
heterocycles,
substrate
scope
reaction
mechanism
discussed
in
detail,
limitations
future
development
prospects
summarized
outlooked.
Molecules,
Journal Year:
2024,
Volume and Issue:
29(15), P. 3567 - 3567
Published: July 29, 2024
Transition-metal-catalyzed
directed
C-H
functionalization
with
various
carbene
precursors
has
been
widely
employed
for
constructing
a
wide
range
of
complex
and
diverse
active
molecules
through
metal
migratory
insertion
processes.
Among
precursors,
iodonium
ylides
serve
as
novel
emerging
precursor
features
including
easy
accessibility,
thermal
stability
high
activity,
which
have
attracted
great
attention
from
organic
chemists
achieved
tremendous
success
in
transformation.
In
this
review,
recent
progress
on
the
application
multifunctional
coupling
characteristics
bond
activation
reactions
is
summarized,
potential
discussed.
The Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
unknown
Published: Aug. 30, 2024
A
novel
Rh(III)-catalyzed
C-H
activation/[5
+
2]
cascade
annulation
of
aroyl
hydrazides
with
iodonium
ylides
is
accomplished,
in
which
diverse
seven-membered
dibenzodiazepinediones
were
afforded
moderate
to
excellent
yields.
This
reaction
features
an
ideal
functional
group
tolerance
and
a
wide
substrate
scope.
Large-scale
derivatization
reactions
conducted
demonstrate
the
potential
utility
this
transformation.
