Advanced Synthesis & Catalysis,
Journal Year:
2024,
Volume and Issue:
366(17), P. 3646 - 3652
Published: June 25, 2024
Abstract
Herein,
we
describe
a
reaction
conditions‐based
switchable
Rh(III)‐catalyzed
C−H
alkylation
and
alkenylation
of
1,2,3‐benzotriazinones
with
maleimides,
where
the
triazinone
serves
as
directing
group
rather
than
its
traditional
role
denitrogenative
precursor.
This
strategy
enables
selective
synthesis
diverse
3‐arylated
succinimides
maleimides
in
up
to
99%
yield
broad
substrate
scope
(48
examples).
Furthermore,
for
first
time,
tandem
coupling
has
been
achieved
by
slightly
modifying
conditions.
Additionally,
gram‐scale
reactions
product
derivatizations
were
conducted
demonstrate
synthetic
utility.
The Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
89(5), P. 3214 - 3225
Published: Feb. 21, 2024
Harnessing
the
organo-palladium
intermediates
generated
from
electrophilic
cyclizations
for
tandem
C–C
bond
construction
is
a
challenging
task
but
constitutes
an
excellent
tool
constructing
complex
motifs
simpler
substrates.
We
realize
herein
such
cyclative
annulation
of
alkynyl-oxime
ethers
with
maleimides
facile
isoxazole-phthalimide
hybrid
through
Pd(II)
catalysis.
This
protocol
features
regio-selectivity
in
C–H
selection,
broad
substrate
scope,
good
functional
group
tolerance,
and
scalability.
Necessary
KIE
&
labeling
studies
give
insight
into
reaction
mechanism.
Organic Letters,
Journal Year:
2023,
Volume and Issue:
25(15), P. 2594 - 2599
Published: April 10, 2023
We
herein
demonstrate
the
acylsilane-directed
Rh-catalyzed
arene
C–H
bond
alkylation
with
maleimides.
The
resulting
derivatives
were
utilized
in
visible-light-induced
intramolecular
siloxycarbene-amide
cyclization
for
synthesis
of
new
tricyclic
γ-lactams.
In
parallel,
we
also
harnessed
same
acylsilane
and
maleimide
units
through
[3
+
2]
carbo-annulation
by
using
Ru-catalysis.
A
wide
range
maleimides
aroylsilanes
used
to
establish
broadness
these
transformations.
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[
The Journal of Organic Chemistry,
Journal Year:
2025,
Volume and Issue:
90(4), P. 1727 - 1732
Published: Jan. 20, 2025
The
insertion
of
carbene
into
secondary
amide
N-H
bonds
remains
underexplored
in
organic
synthesis.
In
this
work,
we
discovered
the
visible-light-induced
siloxycarbene
bonds.
This
metal-free,
facile
reaction
proceeds
with
atom
economy
under
mild
conditions
a
broad
range
amides,
including
benzanilide,
acetanilide,
oxindole,
isatin,
quinolinone,
and
maleimide,
affording
stable
N-
O-acetals
excellent
isolated
yields.
addition,
chemoselective
reveals
robustness
chemical
transformation.
Advanced Synthesis & Catalysis,
Journal Year:
2022,
Volume and Issue:
364(21), P. 3730 - 3735
Published: Sept. 15, 2022
Abstract
Herein,
we
report
a
cobalt‐catalyzed
hydroarylation
of
maleimides
followed
by
an
annulation
sequence
for
the
synthesis
polycyclic
azaheterocycles
in
one
pot.
The
reaction
proceeds
under
redox‐neutral
conditions
and
is
compatible
with
various
functional
groups.
Notably,
as‐prepared
product
exhibits
potential
photophysical
properties.
magnified
image
European Journal of Organic Chemistry,
Journal Year:
2025,
Volume and Issue:
28(5)
Published: Jan. 4, 2025
Abstract
A
stereoselective
Ni−Al
bimetal‐catalyzed
C−H
alkenylation
of
quinazolinones
with
alkynes
has
been
successfully
developed.
Good
selectivity
Z‐type
quinazolinone
products
was
obtained
using
readily
available
substrates,
which
exhibits
a
trans‐configuration
opposite
to
the
conventional
alkynylation
reactions
and
improves
diversity
compounds.
In
addition,
reaction
process
further
explored
through
KIE
other
control
experiments,
possible
mechanism
proposed.
European Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
26(30)
Published: June 15, 2023
Abstract
An
efficient
Rh(III)‐catalyzed
C−H
alkenylation
of
N
‐protected
isoquinolone
with
maleimides
is
reported.
The
carbonyl
group
acts
as
an
inherent
directing
group.
Various
‐substituents
in
the
maleimide,
including
alkyl,
aryl,
and
even
H
−OH,
were
well
tolerated
under
developed
reaction
condition.
This
protocol
showed
broad
substrate
scope,
good
selectivity,
excellent
yields.
Hammett
plot
also
drawn
to
check
effect
substituents
on
progress.
