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.
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(16), С. 11371 - 11379
Опубликована: Июль 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.
The Journal of Organic Chemistry,
Год журнала:
2023,
Номер
89(2), С. 1228 - 1234
Опубликована: Дек. 28, 2023
The
mechanism
of
the
Ac-Gly-OH-assisted
palladium-catalyzed
[3
+
2]
annulation
aromatic
amides
with
maleimides
is
investigated
using
density
functional
theory
calculations.
results
show
that
reaction
undergoes
sequential
steps
N–H
bond
deprotonation,
first
benzylic
C–H
activation,
maleimide
insertion,
second
meta-C–H
reductive
elimination,
and
oxidation.
external
ligand
Ac-Gly-OH
acts
as
internal
base
for
hydrogen
abstraction
in
activation.
insertion
step
found
to
be
rate-determining
step.
Based
on
nearly
same
energetic
span
two
pathways
generate
enantio
products,
computational
are
consistent
experimental
observation
terminal
products
racemic
when
an
achiral
ligand.
These
calculation
disclose
detailed
shed
light
some
ambiguities.
Advanced Synthesis & Catalysis,
Год журнала:
2023,
Номер
365(22), С. 3727 - 3773
Опубликована: Окт. 3, 2023
Abstract
A
variety
of
Pd‐catalyzed
reactions
are
carried
out
with
palladium
carboxylates
in
the
presence
carboxylic
acids
and/or
alkali
metal
carboxylates.
This
review
is
Part
three
reviews
highlighting
dependence
efficiency
formation
different
C−C
bonds
on
nature
carboxylate
unit.
concerns
inter‐
and
intramolecular
leading
to
a
C(
sp
2
)−C(
),
3
)
or
bond.
The
procedures
additives
presented
as
well
reaction
mechanisms
with,
far
possible,
personal
comments.
The Journal of Organic Chemistry,
Год журнала:
2023,
Номер
88(23), С. 16229 - 16247
Опубликована: Ноя. 15, 2023
Herein,
we
report
an
efficient
[3
+
2]
annulation
of
ortho-substituted
iodoarenes
with
maleimides
via
a
palladium-catalyzed
consecutive
double
Heck-type
strategy,
leading
to
fused
tricyclic
frameworks
pharmaceutical
relevance.
The
protocol
ensued
through
inter-
and
intramolecular
Heck
couplings
effectively.
This
approach
was
compatible
large
variety
substrates
functional
groups,
it
remarkably
tolerated
unprotected
maleimide.
Chemical Communications,
Год журнала:
2023,
Номер
59(82), С. 12326 - 12329
Опубликована: Янв. 1, 2023
A
CuBr-mediated
direct
insertion
of
alkenes
into
unstrained
ring
2-aryl-1,3-indandiones
is
reported,
which
provides
a
one-carbon
expansion
strategy
for
the
synthesis
1,4-naphthoquinones.
Entirely
differing
from
existing
reports,
herein
behave
as
C1
units
to
participate
in
annulation
reactions.
This
transformation
facile
route
access
class
highly
functionalized
1,4-naphthoquinones
with
good
yields,
functional-group
tolerance
and
high
atom-economy.
Further
research
on
application
this
reaction
currently
underway
our
laboratory.
Advanced Synthesis & Catalysis,
Год журнала:
2024,
Номер
unknown
Опубликована: Март 20, 2024
Abstract
We
report
herein
a
palladium‐catalyzed,
site‐selective
cyclative
annulation
of
o
‐alkynyl
arylamides
with
maleimide
for
the
stereoselective
construction
succinimide‐fused
benzoxazine
derivatives.
This
operationally
simple
and
modular
protocol
provides
access
to
polycyclic
frameworks.
The
other
associated
features
are
high
functional
group
compatibility,
gram‐scale
synthetic
potential,
downstream
transformations.
Control
labeling
experiments
were
conducted
get
insights
into
mechanism.
Organic Letters,
Год журнала:
2024,
Номер
26(21), С. 4422 - 4426
Опубликована: Май 20, 2024
Catalytic
cyclization
via
dual
C-H
bond
activation
has
evolved
as
a
powerful
strategy
for
building
bi-
and
polycyclic
molecules.
Herein,
palladium-catalyzed
annulation
of
tertiary
anilines
with
3-butenoic
acid
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
unknown
Опубликована: Дек. 3, 2024
The
site-selective
functionalization
of
aromatic
compounds
via
C–H
activation
has
emerged
as
a
popular
tool
in
organic
synthesis.
In
this
study,
we
report
regioselective
coupling
maleimide
to
2-arylbenzo[d]thiazoles
the
presence
rhodium(III)
catalyst.
Depending
upon
nature
substituent
(R2-group)
present
substrate,
either
mono-
or
bis-1,4-addition
products
were
observed
methodology.
case
R2
=
aryl,
cyclohexyl,
and
tert-butyl,
mono
was
observed,
whereas
substituents,
such
methyl,
ethyl,
benzyl,
methyl
thiophene,
provided
bis
major
products.
Similar
selectivity
also
2-arylbenzo[d]oxazoles.
