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.
Organic Letters,
Journal Year:
2023,
Volume and Issue:
25(13), P. 2190 - 2195
Published: March 26, 2023
A
palladium-catalyzed
[3
+
2]
annulation
of
substituted
aromatic
amides
with
maleimides
providing
tricyclic
heterocyclic
molecules
in
good
to
moderate
yields
through
weak
carbonyl
chelation
is
reported.
The
reaction
proceeds
via
a
dual
C-H
bond
activation
where
the
first
takes
place
selectively
at
benzylic
position
followed
by
second
meta
afford
five-membered
cyclic
ring.
An
external
ligand
Ac-Gly-OH
has
been
used
succeed
this
protocol.
plausible
mechanism
proposed
for
reaction.
European Journal of Organic Chemistry,
Journal Year:
2021,
Volume and Issue:
2021(43), P. 5862 - 5879
Published: Oct. 20, 2021
Abstract
Maleimides
and
succinimides
are
all
vital
scaffolds
in
biological
fields
various
natural
products.
Maleimide
derivatives
have
been
extensively
used
as
coupling
partners
for
organic
transformations,
affording
a
broad
array
of
important
molecular
architectures
including
succinimides.
In
the
past
decade,
variety
efficient
chelation‐assisted
strategies
employed
selective
addition
C−H
bonds
to
maleimides
giving
succinimides,
which
also
highly
building
blocks
synthesis.
This
Review
provides
an
overview
research
progress
relating
participated
transition‐metal‐catalyzed
group‐directed
alkylation
from
2012
2021.
Significant
advances
this
field
were
highlighted,
diverse
transition
metal
catalysts,
substrates
contained
different
directing
groups,
reaction
mechanisms
well
synthetic
applications
systematically
discussed.
addition,
limitations
intractable
issues
need
be
solved
future
pointed
out.
Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(7), P. 1338 - 1342
Published: Feb. 9, 2024
A
palladium-catalyzed
(3
+
2)
annulation
of
2-methylbenzoic
acid
with
maleimide
using
Ac-Leu-OH
as
a
powerful
ligand
has
been
reported.
Through
site-selective
γ-C(sp3)–H
olefination
reaction
and
sequential
decarboxylative
cross-coupling
reaction,
five-membered
cyclic
ring
was
obtained
the
final
product.
This
novel
features
great
site
selectivity
reactivity
to
generate
various
products
in
moderate
good
yields.
ACS Catalysis,
Journal Year:
2024,
Volume and Issue:
14(8), P. 5605 - 5611
Published: March 29, 2024
The
development
of
benzylic
C(sp3)–H
functionalization
methods
for
the
assembly
derivatives
has
been
extensively
explored
in
recent
years.
However,
engagement
carbon
and
its
adjacent
C=C
bond
as
a
C3
synthon
cycloaddition
reaction
via
direct
C–H
activation
is
rare.
Herein,
we
report
copper-catalyzed
[3+3]
radical
through
to
construct
six-membered
cyclohexane-type
rings.
In
this
reaction,
2-benzylic
an
indole
selectively
activated
serves
that
reacts
highly
chemoselective
intermolecular
self-[3+3]
cross-[3+3]
pathways.
Multiple
symmetric
nonsymmetric
polycyclic
hexahydrocarbazole
scaffolds
with
hexacyclic
6/5/5/6/5/5/6
pentacyclic
6/5/5/6/5/6
ring
systems
are
synthesized
high
efficiency
chemoselectivity
using
strategy.
Inspired
by
unique
addition
pathway
cycloaddition,
controllable
construction
C3a-alkylated
pyrroloindolines
was
also
developed.
ACS Catalysis,
Journal Year:
2024,
Volume and Issue:
14(9), P. 6535 - 6546
Published: April 15, 2024
Palladium-catalyzed
C–H
annulation
reactions
represent
a
compelling
strategy
to
construct
complex
ring
systems
with
high
step
economy.
While
there
are
many
approaches
annulate
structures
by
activation
of
single
bond,
transformations
that
proceed
multiple
bonds
less
explored.
This
is
especially
true
for
examples
where
one
the
reacting
located
at
an
sp3
center.
However,
exciting
developments
in
palladium-catalyzed
continue
expand
scope
these
and
provide
innovative
strategies
challenging
carbon–carbon
bonds.
From
discoveries,
sequential
activations
have
emerged
as
powerful
tool
access
through
C(sp2)–H/C(sp3)–H
or
C(sp3)–H/C(sp3)–H
In
this
Perspective,
we
showcase
recent
use
order
highlight
synthetic
potential
activation-enabled
annulations
inspire
future
disconnections
diverse
scaffold
synthesis.
Journal of the American Chemical Society,
Journal Year:
2023,
Volume and Issue:
145(17), P. 9464 - 9470
Published: April 20, 2023
Given
the
wide
availability
and
low
cost
of
alkylbenzenes,
direct
C-H
functionalization
these
aromatic
hydrocarbons
to
afford
structurally
complex
building
blocks
has
long
been
interest
in
organic
synthesis.
Herein
we
describe
a
method
for
rhodium-catalyzed
dehydrogenative
(3
+
2)
cycloaddition
reactions
alkylbenzenes
with
1,1-bis(phenylsulfonyl)ethylene.
The
π-coordination
rhodium
catalyst
facilitates
benzylic
deprotonation,
allowing
subsequent
which
metal-complexed
carbanion
serves
as
unique
all-carbon
1,3-dipole
equivalent.
We
demonstrated
generality
this
catalytic
by
carrying
out
large
array
generate
dihydroindene
derivatives
bearing
two
synthetically
versatile
sulfonyl
groups.
Quantum-chemical
calculations
revealed
details
reaction
process.
Angewandte Chemie International Edition,
Journal Year:
2023,
Volume and Issue:
62(40)
Published: July 28, 2023
The
control
of
the
reactivity
diazo
compounds
is
commonly
achieved
by
choice
a
suitable
catalyst,
e.g.
via
stabilization
singlet
carbenes
or
radical
intermediates.
Herein,
we
report
on
light-promoted
cyclic
imides
with
thiols,
where
solvent
results
in
two
fundamentally
different
reaction
pathways.
In
dichloromethane
(DCM),
carbene
formed
initially
and
engages
cascade
C-H
functionalization/thiolation
to
deliver
indane-fused
pyrrolidines
good
excellent
yields.
When
switching
acetonitrile
solvent,
pathway
shut
down
an
unusual
reduction
compound
occurs
under
otherwise
identical
conditions,
aryl
thiol
acts
as
reductant.
A
combined
set
experimental
computational
studies
was
carried
out
obtain
mechanistic
understanding
support
that
indane
formation
proceeds
insertion
triplet
carbene,
while
electron
transfer
process.
Organic Letters,
Journal Year:
2023,
Volume and Issue:
25(34), P. 6305 - 6310
Published: Aug. 22, 2023
An
efficient
method
for
the
synthesis
of
bicyclic
spirodiamine
molecules
via
β-C(sp3)–H
bond
activation
aliphatic
amides,
followed
by
cyclization
with
maleimides,
has
been
developed.
The
reaction
proceeds
through
an
amide-directed
alkyl
amides
and
subsequent
maleimides.
methodology
is
highly
compatible
a
wide
variety
Amides
derived
from
biologically
active
fatty
acids
were
also
found
to
be
protocol.
A
palladacycle
was
synthesized
intermediate
in
this
reaction.
plausible
mechanism
proposed
account
spirocyclization.
Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(29), P. 6209 - 6213
Published: July 12, 2024
Palladium-catalyzed
intermolecular
[3
+
2]
annulation
reactions
via
C-H
activation
represent
a
powerful
and
charming
tool
for
assembling
cyclopentanes.
Herein,
we
have
developed
strategy
the
palladium-catalyzed
alkene-relayed
reaction
of
aryl
iodides
maleimides
C(sp
