The Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
88(11), P. 7489 - 7497
Published: April 28, 2023
A
designed
method
for
the
preparation
of
3-aminomethylated
maleimides
via
Morita–Baylis–Hillman
(MBH)
reaction
was
developed.
This
phosphine-catalyzed
coupling
adopted
and
1,3,5-triazinanes
as
substrate,
giving
a
series
maleimide
derivatives
with
double
bond
retained
on
ring
in
41–90%
yield.
Acylation,
isomerization,
Michael
addition
obtained
products
demonstrated
synthetic
application
present
protocol.
The
results
control
experiments
indicated
that
phosphorus
ylide
formation
elimination
take
place
during
pathway.
Chemistry - A European Journal,
Journal Year:
2022,
Volume and Issue:
28(39)
Published: May 7, 2022
A
palladium-catalyzed
[3+2]
annulation
of
substituted
benzoic
acids
with
maleimides
leading
to
tricyclic
heterocyclic
molecules
having
a
free
carboxylic
group
in
high
atom-
and
step-economical
manner
is
described.
The
reaction
proceeds
via
dual
C-H
bond
activation
such
as
C(sp3
)-H
at
the
benzylic
position
C(sp2
meta
aromatics.
An
external
ligand
(MPAA)
crucial
for
success
present
protocol.
Further,
decarboxylation
esterification
acid
observed
products
were
carried
out.
Chemical Science,
Journal Year:
2024,
Volume and Issue:
15(48), P. 20346 - 20354
Published: Jan. 1, 2024
A
highly
site-selective
decarbonylative
[4
+
2]
cyclization
of
carboxylic
acids
with
terminal
alkynes
forming
naphthalenes
is
enabled
by
palladium
cluster
catalysis.
Chemical Communications,
Journal Year:
2021,
Volume and Issue:
57(66), P. 8194 - 8197
Published: Jan. 1, 2021
A
new
edition
of
[5+1]
annulation
reaction
maleimides
with
2-alkenylphenols
has
been
discovered
under
a
Rh(III)-catalytic
system.
The
process
leads
to
an
efficient
synthesis
valued
spirocyclic
scaffolds
bearing
oxygen-containing
spiro
carbon
in
single
step
and
shows
broad
substrate
scope
good
functional
group
tolerance.
synthetic
utility
exemplified
by
synthesizing
highly
functionalized
2,2-disubstituted-2H-chromene
skeletons
gram-scale
low
catalyst
loading.
Advanced Synthesis & Catalysis,
Journal Year:
2023,
Volume and Issue:
365(18), P. 3118 - 3128
Published: July 27, 2023
Abstract
Switchable
synthesis
of
3‐alkenyl
succinimides
and
maleimides
has
been
achieved
via
Michael
addition
oxidative
cross‐coupling
reaction
α‐oxo
ketene
dithioacetals
by
switching
different
conditions.
In
the
presence
30
mol%
CH
3
SO
H
in
DCE
at
120
°C,
occurred
to
afford
40–90%
yields,
whereas
Pd(OAc)
2
DMF
20
were
obtained
40–80%
yields
from
with
maleimides.
The
presupposition
directing
groups
onto
substrates
is
not
required
reaction.
method
can
be
extended
gram
scale.
The Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
88(20), P. 14264 - 14273
Published: Oct. 9, 2023
Intermolecular
(3
+
2)
annulation
emerges
as
a
potent
approach
for
constructing
5-membered
carbocycles
through
the
fusion
of
two
distinct
components.
This
synopsis
encapsulates
recent
strides
in
realm
transition-metal-catalyzed
dehydrogenative
aromatic
hydrocarbons,
achieved
dual
functionalization
benzylic
and
ortho
C–H
bonds.
Encompassing
three
pivotal
strategies,
namely,
(i)
bond
activation,
(ii)
oxidation,
(iii)
π-coordination
this
review
offers
an
overview
field's
developments.
Chemical Communications,
Journal Year:
2024,
Volume and Issue:
60(49), P. 6284 - 6287
Published: Jan. 1, 2024
A
palladium-catalyzed
dual
C-H
functionalization
of
substituted
aromatic
ketones
and
ester
with
maleimides
leading
to
tricyclic
heterocyclic
molecules
good
excellent
yield
is
reported.
In
this
protocol,
weak
chelation
the
carbonyl
groups
has
been
successfully
utilized
for
selective
activation
The Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
89(16), P. 11371 - 11379
Published: July 29, 2024
The
mechanism
of
palladium-catalyzed
annulation
reactions
benzamide-
and
anilide-type
aromatic
systems
with
maleimides
is
investigated
using
density
functional
theory.
Double
C–H
bond
activation
key
to
forming
the
desired
product.
first
for
anilide-
amide-type
ligands
can
occur
at
ortho
benzylic
bonds,
while
second
occurs
meta
carbon
rings.
For
system,
activations
via
four-
five-membered
palladacycles,
respectively.
In
contrast,
benzamide-type
five-
six-membered
energy
span
model
suggests
that
initial
step
position
determines
turnover
frequency
both
systems.
Energy
decomposition
analysis
distortion-interaction/activation-strain
analyses
are
employed
understand
electronic
steric
factors
controlling
frequency-determining
transition
state.
Macromolecules,
Journal Year:
2022,
Volume and Issue:
55(14), P. 5985 - 5996
Published: July 14, 2022
Three
new
N-arylmaleimide-based
Pd(0)
complexes
[Pd(N-phenylmaleimide)2(2,5-norbornadiene)
(1),
Pd(N-2,6-difluorophenylmaleimide)2(2,5-norbornadiene)
(2),
and
Pd(N-2,6-difluorophenylmaleimide)2(dibenzylideneacetone)
(3)]
were
prepared
used
as
an
initiator
in
conjunction
with
NaBPh4
[Pd(N-arylmaleimide)/NaBPh4
system]
for
polymerization
of
diazoacetates.
The
Pd(N-arylmaleimide)/NaBPh4
system
polymerized
a
series
diazoacetates
(ethyl,
benzyl,
cyclohexyl
diazoacetates)
to
yield
polymers
moderate
good
yield,
particularly
showing
high
activity
diazoacetate.
Matrix-assisted
laser
desorption/ionization
time-of-flight
mass
spectrometry
(MALDI-TOF-MS)
analysis
other
experimental
observations
revealed
the
incorporation
one
N-arylmaleimide
molecule
coordinated
on
Pd
center
into
α-chain
end
obtained
initiating
system,
indicating
that
species
was
generated
by
insertion
Pd–Ph
linkage,
which
first
formed
reaction
complex
NaBPh4,
would
enable
syntheses
α-chain-end-functionalized
poly(alkoxycarbonylmethylene)s.
