Organic Letters,
Journal Year:
2023,
Volume and Issue:
25(16), P. 2923 - 2927
Published: April 17, 2023
An
efficient
approach
for
the
synthesis
of
N-substituted
indenoisoquinolinones
via
rhodium(III)-catalyzed
C-H
bond
activation/subsequent
[4
+
2]
cyclization
starting
from
easily
available
2-phenyloxazolines
and
2-diazo-1,3-indandiones
has
been
developed.
A
series
indeno[1,2-c]isoquinolinones
were
obtained
in
up
to
93%
yield
through
functionalization,
followed
by
intramolecular
annulation,
elimination,
ring-opening
a
"one
pot
manner"
under
mild
reaction
conditions.
This
protocol
features
excellent
atom-
step-economy
provides
novel
strategy
chance
study
their
biological
activities.
Organic & Biomolecular Chemistry,
Journal Year:
2021,
Volume and Issue:
19(7), P. 1438 - 1458
Published: Jan. 1, 2021
The
review
highlighted
diverse
annulations,
including
nitrogen,
oxygen,
sulfur
heterocycles
and
carbocylizations
via
Rh(iii)/Ir(iii)-catalyzed
C–H
functionalization/annulation
with
various
arene
carbene
precursors.
Organic Letters,
Journal Year:
2021,
Volume and Issue:
23(11), P. 4233 - 4238
Published: May 21, 2021
Herein,
we
report
an
acid-controlled
highly
tunable
selectivity
of
Rh(III)-catalyzed
[4
+
2]
and
[3
3]
annulations
N-carboxamide
indoles
with
iodonium
ylides
lead
to
form
synthetically
important
tricyclic
tetracyclic
N-heterocycles.
Here,
ylide
serves
as
a
carbene
precursor.
The
protocol
proceeds
under
operationally
simple
conditions
provides
novel
scaffolds
such
3,4-dihydroindolo[1,2-c]quinazoline-1,6(2H,5H)-dione
1H-[1,3]oxazino[3,4-a]indol-1-one
derivatives
broad
range
functional
group
tolerance
moderate
excellent
yields.
Furthermore,
the
synthetic
utility
was
extended
for
various
chemical
transformations
easily
scaled
up
large-scale
level.
Journal of the American Chemical Society,
Journal Year:
2020,
Volume and Issue:
142(41), P. 17306 - 17311
Published: Sept. 28, 2020
The
Ni-catalyzed
reaction
of
ortho-fluoro-substituted
aromatic
amides
with
alkynes
results
in
C–F/N–H
annulation
to
give
1(2H)-isoquinolinones.
A
key
the
success
is
use
KOtBu
or
even
weak
base,
such
as
Cs2CO3.
proceeds
absence
a
ligand
and
under
mild
conditions
(40–60
°C).
DFT
calculations
suggest
that
pathway
for
this
involves
N−H
deprotonation,
oxidative
addition
C–F
bond,
migratory
insertion
an
alkyne,
reductive
elimination
form
1(2H)-isoquinolinone
derivatives.
Chemical Communications,
Journal Year:
2022,
Volume and Issue:
58(41), P. 6140 - 6143
Published: Jan. 1, 2022
Highly
selective
and
switchable
[4+2]
annulations
of
2-arylindoles
with
iodonium
ylides
were
achieved
by
performing
solvent-controlled
Rh(III)-catalyzed
C-H
activations.
When
using
DCM
as
a
solvent,
the
functionalization
selectively
delivered
indolo[2,1-a]isoquinoline
derivatives.
In
contrast,
same
catalytic
system
polar
HFIP
solvent
predominately
provided
benzo[a]carbazole
moieties.
Organic Letters,
Journal Year:
2019,
Volume and Issue:
21(16), P. 6437 - 6441
Published: Aug. 6, 2019
Rhodium-catalyzed
substrate-tunable
oxidative
annulation
and
spiroannulation
reactions
of
2-arylindoles
with
benzoquinone
leading
to
9H-dibenzo[a,c]carbazol-3-ols
new
spirocyclic
products
are
reported.
Intriguingly,
2-aryl-substituted
indoles,
could
act
as
a
C2
synthon
afford
dibenzo[a,c]carbazoles.
On
the
contrary,
when
2-aryl-3-substituted
indoles
were
used,
switched
C1
furnish
compounds.
In
addition,
further
transformations
obtained
demonstrate
synthetic
utility
present
protocol.
Angewandte Chemie International Edition,
Journal Year:
2021,
Volume and Issue:
60(39), P. 21327 - 21333
Published: June 28, 2021
A
catalytic
system-controlled
divergent
reaction
strategy
was
here
reported
to
construct
four
types
of
intriguing
spiroheterocyclic
skeletons
from
simple
and
readily
available
starting
materials
via
a
precise
chemical
bond
activation/[n+1]
annulation
cascade.
The
tetraazaspiroheterocyclic
trizazspiroheterocyclic
scaffolds
could
be
independently
constructed
by
selective
N-N
cascade,
C(sp2
)-H
activation/[4+1]
novel
tandem
)-H/C(sp3
strategy,
along
with
broad
scope
substrates,
moderate
excellent
yields
valuable
transformations.
More
importantly,
in
these
transformations,
we
are
the
first
time
capture
activation
C(sp3
pyrazolidinones
under
different
system.
Chemical Communications,
Journal Year:
2020,
Volume and Issue:
56(41), P. 5528 - 5531
Published: Jan. 1, 2020
Rhodium(iii)-catalyzed
C–H
activation
of
oximes
and
benzoic
acids
has
been
realized
in
oxidative
annulation
with
quinone
diazides
for
synthesis
spirocycles.
Advanced Synthesis & Catalysis,
Journal Year:
2019,
Volume and Issue:
362(4), P. 913 - 926
Published: Dec. 17, 2019
Abstract
A
selective
synthesis
of
5,6‐disubstituted
and
5‐substituted
indazolo[2,3‐
a
]quinolines
through
Rh(III)‐catalyzed
oxidant‐free
annulation
2‐aryl‐2
H
‐indazoles
with
α
‐diazo
carbonyl
compounds
is
reported.
With
as
the
substrates,
α‐diazo
could
act
C2
synthon
to
afford
via
[4+2]
annulation.
On
other
hand,
when
2‐aryl‐3‐formyl‐2
were
used
switched
C1
undergo
more
complicated
[5+1]
process
furnish
]quinolines.
magnified
image
Chemical Communications,
Journal Year:
2021,
Volume and Issue:
57(67), P. 8268 - 8271
Published: Jan. 1, 2021
Catalytic
asymmetric
[4+1]
spiroannulation
of
O
-pivaloyl
oximes
with
α-diazo
homophthalimides
has
been
realized
for
enantioselective
synthesis
spirocyclic
imines.
