An
efficient
synthesis
of
indazole
fused
phenanthridinones
via
Rh(III)-catalyzed
inert
C(sp2)-H
activation/
[4+2]
annulation
3-aryl-1H-indazoles
with
iodonium
ylides
has
been
developed,
providing
a
strategy
to
access
multi-conjugated
π-system
tetracyclic
and
pentacyclic
aza-heterocyclics.
This
“one-pot”
reaction
features
high
efficiency,
excellent
regioselectivity,
broad
substrate
compatibility
could
be
easily
scaled
up.
Notably,
the
photoluminescent
properties
desired
products
appear
charming
valuable.
The
obtained
exhibits
low
toxicity
in
MDCK
cells
as
well
selectively
label
zebrafish
larvae,
which
indicated
that
titled
potentially
utilized
biofluorescent
probes
or
fluorescent
dyes.
Chemical Reviews,
Год журнала:
2024,
Номер
unknown
Опубликована: Сен. 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,
Год журнала:
2024,
Номер
26(24), С. 5136 - 5140
Опубликована: Июнь 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.
Advanced Synthesis & Catalysis,
Год журнала:
2024,
Номер
366(8), С. 1744 - 1750
Опубликована: Фев. 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.
Organic Letters,
Год журнала:
2023,
Номер
25(15), С. 2582 - 2587
Опубликована: Апрель 10, 2023
Transition
metal-controlled
divergent
annulation
reactions
of
azomethine
imines
with
iodonium
ylides
via
C-centered
[1,2]-rearrangement
have
been
developed.
The
imino
group,
as
a
switchable
and
transient
directing
group
(DG),
underwent
intramolecular
nucleophilic
addition
in
situ
generated
bicyclic
diaziridine,
which
facilitated
the
subsequent
annulations
presence
different
metal
complexes
catalysts.
benzo[c]chromen-1-one
pyrano[de]isochromene
scaffolds
could
be
independently
constructed
Rh(III)
Ru(II),
respectively.
It
was
worth
noting
that
employed
first
DG
through
rearrangement
progress.
Chemical Communications,
Год журнала:
2024,
Номер
60(51), С. 6560 - 6563
Опубликована: Янв. 1, 2024
A
Rh(
iii
)-catalyzed
C–H/N–H
[4+2]
annulation
of
oxadiazolones
with
iodonium
ylides
was
developed,
which
afforded
a
series
fused-isoquinolines
and
fused-pyridines.
The Journal of Organic Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Март 21, 2025
Herein,
an
efficient
Rh-catalyzed
C-H
activation/annulation
between
α,β-unsaturated
amides
and
coumarin-derived
iodonium
ylides
has
been
developed,
affording
novel
pyrano[3,2-c]chromene-2,5-diones
analogues
in
high
yields.
Most
products
could
be
easily
isolated
by
precipitation
ethanol,
followed
simple
filtration.
Additionally,
this
protocol
demonstrated
the
benefits
of
environmentally
friendly
conditions,
air
compatibility,
good
functional
group
scale-up
synthesis
with
low
catalyst
loading,
a
recyclable
Rh
catalyst.
Importantly,
compounds
3m
3w
moderate
agonist
activity
on
TASK-3
channel,
I/I0
values
1.7650
±
0.1058
1.400
0.0589,
respectively.
Organic Chemistry Frontiers,
Год журнала:
2024,
Номер
11(6), С. 1811 - 1816
Опубликована: Янв. 1, 2024
An
efficient
protocol
to
construct
spiro[indole-3,4′-pyrazol]-5′-ones
via
ruthenium(
ii
)-catalyzed
selective
C–H
bond
activation/[4
+
1]
spirocyclization
starting
from
easily
available
N
-aryl
amidines
and
diazopyrazolones
has
been
developed.
Applied Organometallic Chemistry,
Год журнала:
2024,
Номер
38(9)
Опубликована: Июль 5, 2024
A
novel
Rh‐catalyzed
three‐component
synthesis
of
N
‐(
o
‐alkylaryl)
pyrazoles
via
cascade
pyrazole
annulation
and
aryl
C‐H
conjugate
addition
to
alkenes
has
been
developed
with
enaminones,
hydrazines,
functionalized
as
starting
materials.
The
raw
materials
used
in
this
reaction
are
simple,
cheap,
readily
available,
the
reactions
feature
excellent
step
economy
by
furnishing
products
formation
a
ring
key
activation
one‐step
operation.
Moreover,
proceeds
smoothly
under
air
atmosphere,
making
it
easy
operate.
Organic Letters,
Год журнала:
2024,
Номер
26(31), С. 6625 - 6630
Опубликована: Авг. 1, 2024
By
employing
elemental
selenium
as
the
source,
we
have
realized
amidine-directed
Rh(III)-catalyzed
cascade
C–H
selenylation/[5
+
1]
annulation
for
direct
construction
of
structurally
novel
selenadiazine,
benzoselenadiazine,
and
benzoselenazol-3-amine
frameworks
with
specific
site
selectivity
good
functional
group
tolerance.
Besides,
obtained
products
can
serve
fundamental
platforms
subsequent
chemical
transformations,
thus,
feasible
SeNEx
reaction,
SeNEx/Michael
addition,
simple
conversion
selenadiazine
product
into
diverse
other
organoselenium
molecules
were
demonstrated
accordingly.
Taken
together,
developed
methodology
efficiently
expands
space
species.
