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.
Chinese Journal of Chemistry,
Journal Year:
2022,
Volume and Issue:
40(21), P. 2502 - 2506
Published: July 23, 2022
Comprehensive
Summary
A
new
method
for
post‐assembly
modification
of
peptides
via
the
Pd‐catalyzed
endogenous
group‐directed
sp
3
C—H
arylation
with
aryl
iodides
is
developed.
The
sulfide
side
chain
methionine
(Met)
residue
can
facilitate
both
β
and
γ
methyl
bonds
N‐terminal
aliphatic
amino
acids
formation
5
or
6‐membered
palladacycle
intermediates.
reactions
proceed
in
moderate
to
good
yield
excellent
diastereoselectivity.
Chemistry - An Asian Journal,
Journal Year:
2023,
Volume and Issue:
18(18)
Published: Aug. 4, 2023
Abstract
The
palladium‐catalyzed
reaction
of
aromatic
amides
with
maleimides
results
in
the
formation
a
double
C−H
bond
activation
product,
which
occurs
at
both
benzylic
and
meta
positions.
Computational
chemistry
studies
suggest
that
first
unfolds
via
six‐membered
palladacycle,
maleimide
insertion,
protonation
Pd−N
bond,
then
bond.
process
concludes
reductive
elimination,
producing
an
annulation
product.
energy
decomposition
analysis
(EDA)
showed
deformation
favors
ortho
process.
However,
this
route
is
non‐productive.
interaction
controls
site
where
inserted
into
Pd−C(sp
3
)
determines
its
selectivity.
energetic
span
model
indicates
step
one
turnover
frequency.
Regarding
directing
group,
it
has
been
concluded
strong
Pd−S
bonding
destabilizing
effect
allow
2‐thiomethylphenyl
to
function
effectively
as
group.
Organic Letters,
Journal Year:
2022,
Volume and Issue:
24(49), P. 9060 - 9064
Published: Dec. 1, 2022
Alkene-relayed
C-H
activation
represents
a
novel
strategy
for
functionalizing
bonds
selectively.
We
developed
Pd-catalyzed
annulation
reaction
of
2-iodobiphenyls
with
maleimides
that
act
as
relay
alkylation.
The
features
broad
substrate
scope
and
high
efficiency,
providing
straightforward
method
the
synthesis
succinimide-fused
9,10-dihydrophenanthrenes.
using
acenaphthylene
has
also
been
developed,
which
allows
easy
access
to
dibenzo[j,l]fluoranthenes.
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.
