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.
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.
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.
A
concise
synthesis
of
benzodiazepines
via
Rh(III)
catalyzed
C-H
activation/
[4
+
3]
annulation
easily
available
1-arylpyrazolidinones
with
allylic
acetal
has
been
developed.
The
was
employed
as
a
novel
3C
synthon
in
this
transformation.
Benzodiazepines
were
built
under
mild
reaction
conditions
high
efficiency
and
chemoselectivity.
atom-economy
accessible
substrates
reveal
potential
application.
The Journal of Organic Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Май 29, 2025
Iridium(III)-catalyzed
regioselective
cyclization
of
substituted
oximes
with
iodonium
ylides
has
been
described.
This
methodology
offered
multisubstituted
heterocyclic
N-oxides
under
mild
reaction
conditions
in
a
redox-neutral
manner.
The
was
also
compatible
vinyl
oximes.
Additionally,
substrate
diversification
carried
out
to
illustrate
the
synthetic
application
protocol.
A
possible
mechanism
involving
C-H
bond
activation
proposed
as
well
supported
by
isolation
key
five-membered
iridacycle
intermediate.
Molecules,
Год журнала:
2024,
Номер
29(15), С. 3567 - 3567
Опубликована: Июль 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.
Chinese Journal of Chemistry,
Год журнала:
2024,
Номер
42(17), С. 1986 - 1992
Опубликована: Апрель 25, 2024
Comprehensive
Summary
The
rhodium‐catalyzed
C—H
bond
activation
and
cyclization
of
3‐oxopent‐4‐enenitriles
with
alkynes
proceed
efficiently.
Various
2
H
‐pyrans
multiple
substituents
are
achieved
in
good
yields
through
regioselective
formation
C—O
C—C
bonds.
Transformations
involving
hydroxy‐alkynoates
resulted
products
a
furo[3,4‐
b
]pyran
skeleton
via
further
intramolecular
ester
exchange
processes.
Different
from
the
traditional
“1‐oxatrienes
pathway”,
this
method
for
synthesis
useful
possesses
certain
highlights
terms
readily
available
substrates,
stable
easily
derivatized
products,
gentle
convenient
operation
process,
step
atom
economy.
Chemistry - A European Journal,
Год журнала:
2024,
Номер
30(43)
Опубликована: Май 10, 2024
Thanks
to
the
ability
of
diazo
derivatives
react
either
as
1,3-dipoles
and
carbenes
after
dinitrogen
extrusion,
combinations
oxa
or
aza
benzonorbornadienes
diazomalonates
afford
polycyclic
pyrazolidines
via
a
three-step
sequence
(i)
highly
diastereoselective
[3+2]-cycloaddition,
(ii)
CpRu-catalyzed
carbene
addition,
(iii)
second
dipolar
cycloaddition.
Of
importance,
step
(II)
represents
unique
access
novel
bench-stable
N,N-cyclic
azomethine
imines,
which
behave
effective
in
combination
with
electron-poor
dipolarophiles.
Each
proceeds
efficiently
3-step
process
can
be
performed
one-pot
yield
pyrazolidine
excellent
overall
(90
%).
Bulletin of the Korean Chemical Society,
Год журнала:
2023,
Номер
45(2), С. 131 - 144
Опубликована: Дек. 12, 2023
Abstract
The
synthesis
and
functionalization
of
privileged
nitrogen
heterocycles
has
emerged
as
a
central
topic
in
drug
discovery
material
science.
In
this
context,
the
tandem
C–H
intramolecular
annulation
received
prodigious
attention,
it
is
able
to
expedite
construction
heteroaromatic
frameworks
beyond
conventional
functionalization.
general,
significant
effort
been
made
develop
[3
+
2]
dipolar
cycloaddition
azomethine
imines
with
π‐unsaturated
compounds.
Moreover,
3],
[4
2
2],
[5
3]
reactions
various
dipolarophiles
have
demonstrated.
To
date,
however,
combination
catalytic
cyclization
using
both
directing
groups
units
less
explored.
This
review
focuses
on
recent
progress
toward
azomethines
range
coupling
partners.
