Advanced Synthesis & Catalysis,
Год журнала:
2024,
Номер
366(13), С. 2926 - 2932
Опубликована: Май 15, 2024
Abstract
An
intermolecular
annulation
reaction
of
2‐aryl‐1,3‐indandions
with
alkynes
was
reported
using
Pd(OAc)
2
to
access
spirobi[indene]‐1,3‐diones.
Under
palladium
catalysis,
the
substrates
form
a
homocoupling
dimer
intermediate
through
catalytic
dehydrogenative
cross‐coupling
process.
The
palladium(II)
species
could
come
from
or
2‐aryl‐1,3‐indandion.
Notably,
this
pathway
is
not
typically
observed
in
enol‐directed
formal
sp
3
C−H
functionalization/oxidative
chemistry.
This
transformation
provides
route
class
functionalized
spiro
carbocyclic
indenes.
Angewandte Chemie International Edition,
Год журнала:
2023,
Номер
62(40)
Опубликована: Июль 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,
Год журнала:
2024,
Номер
26(7), С. 1338 - 1342
Опубликована: Фев. 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,
Год журнала:
2024,
Номер
14(9), С. 6535 - 6546
Опубликована: Апрель 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.
Organic Letters,
Год журнала:
2024,
Номер
26(29), С. 6209 - 6213
Опубликована: Июль 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
Organic Letters,
Год журнала:
2023,
Номер
25(34), С. 6305 - 6310
Опубликована: Авг. 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.
The Journal of Organic Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Апрель 4, 2025
An
efficient
method
for
the
synthesis
of
polycyclic
molecules
via
cobalt-catalyzed
[2
+
2
2]
followed
by
[4
consecutive
cycloaddition
reaction
strategy
has
been
devised.
Sequential
reactions
substituted
1,6-diynes
with
maleimides
have
performed.
This
tandem
approach
yielded
polyheterocyclic
compounds
exhibiting
remarkable
diastereoselectivity
and
achieving
yields
ranging
from
good
to
excellent.
Additionally,
a
potential
mechanism
proposed
explain
observed
process.
The Journal of Organic Chemistry,
Год журнала:
2023,
Номер
88(20), С. 14264 - 14273
Опубликована: Окт. 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,
Год журнала:
2024,
Номер
60(49), С. 6284 - 6287
Опубликована: Янв. 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
Chemistry - An Asian Journal,
Год журнала:
2023,
Номер
18(18)
Опубликована: Авг. 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.
