Advanced Synthesis & Catalysis,
Год журнала:
2023,
Номер
366(2), С. 183 - 187
Опубликована: Ноя. 30, 2023
Abstract
Herein
a
Pd(II)‐catalyzed
C−H
silylation
of
o
‐alkynylanilines
with
hexamethyldisilane
for
the
synthesis
disilylated
2‐phenyl‐1
H
‐indoles
is
reported.
In
this
reaction,
undergo
an
aminopalladation,
activation,
and
dealkylation
sequence
to
form
five‐membered
C
,
‐palladacycles,
which
then
couple
construct
one
C−N
bond
two
C−Si
bonds.
This
method
provides
alternative
strategy
silylation.
ACS Catalysis,
Год журнала:
2023,
Номер
13(19), С. 12692 - 12699
Опубликована: Сен. 14, 2023
Accomplished
herein
is
a
rearrangement
strategy
for
the
highly
efficient
assembly
of
synthetically
cumbersome
while
medicinally
significant
2-amino-3-formyl
chromones
via
palladium-catalyzed
ring-opening,
rearrangement,
and
cyclization
process.
Such
sequence
enables
formation
one
C(sp2)–O
bond
C(sp2)–C(sp2)
bond,
reconstruction
benzo-γ-pyrone
moiety
in
single
operation,
thus
producing
difunctionalized
chromone-incorporated
derivatives.
The
reaction
proceeds
shorter
time
(30
min
3-iodochromones
most
cases)
atom-
step-economical
manner.
synthetic
application
current
protocol
further
demonstrated
by
late-stage
modification
pharmaceuticals
their
intermediates,
gram-scale
reactions,
transformations
functional
groups,
as
well
synthesis
bioactive
molecules
drugs.
Mechanistic
studies
indicate
that
nucleophilic
ring-opening
process
moiety,
phenoxy
anion
intermediate,
an
intramolecular
might
be
involved
present
system.
Chinese Journal of Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Фев. 14, 2025
Comprehensive
Summary
We
developed
a
novel
Pd‐catalyzed
carbonylation
of
ortho
‐alkenyl
iodobenzenes
with
CO,
affording
diverse
array
3‐arylindenones
in
good
to
excellent
yields
(up
94%
yield).
This
methodology
exhibits
broad
substrate
scope
and
functional
group
compatibility.
The
synthetic
utility
was
demonstrated
by
gram‐scale
reaction,
product
derivatizations,
the
preparation
an
intermediate
for
PPARγ
agonist.
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(6), С. 4085 - 4097
Опубликована: Фев. 23, 2024
A
palladium-catalyzed
annulative
π-extension
reaction
of
bay-iodinated
triphenylenes
with
aryl
iodides/o-chloroaromatic
carboxylic
acids
was
developed.
This
approach
enabled
the
synthesis
diverse
polycyclic
aromatic
compounds,
including
dibenzo[fg,op]tetracenes,
azadibenzo[fg,op]tetracenes,
and
tribenzo[a,g,m]coronenes.
Initial
studies
indicate
that
resulting
product,
2,3,8,9,14,15-hexakis(decyloxy)tribenzo[a,g,m]coronene,
exhibits
good
liquid-crystalline
properties.
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
Angewandte Chemie International Edition,
Год журнала:
2024,
Номер
63(45)
Опубликована: Июль 25, 2024
Abstract
C−H
bond
functionalization
involving
C
,
‐palladacycle
intermediates
provides
a
unique
platform
for
developing
novel
reactions.
However,
the
vast
majority
of
studies
have
been
limited
to
transformations
(aryl),
‐palladacycles.
In
sharp
contrast,
catalytic
reactions
(alkyl),
(alkyl)‐palladacycles
rarely
reported.
Herein,
we
disclose
an
unprecedented
cascade
C(sp
3
)−H
annulation
(alkyl)‐palladacycles.
this
protocol,
alkene‐tethered
cycloalkenyl
bromides
undergo
intramolecular
Heck/C(sp
activation
generate
(alkyl)‐palladacycles,
which
can
be
captured
by
α
‐bromoacrylic
acids
afford
tricyclic
fused
pyridinediones.
addition,
strategy
also
applied
indole‐tethered
construct
pentacyclic
pyridinediones
via
suquential
Heck
dearomatization/C(sp
activation/decarboxylative
cyclization.
Notably,
removal
in
reaction
build
interesting
skeleton
containing
four‐membered
ring.
Preliminary
mechanistic
experiments
indicate
that
five‐membered
serve
as
key
intermediates.
Meanwhile,
density
functional
theory
(DFT)
calculations
provided
insights
into
pathway.
Chemical Communications,
Год журнала:
2025,
Номер
unknown
Опубликована: Янв. 1, 2025
A
sequential
three-component
intermolecular
carbopalladation/Heck
cyclization/intermolecular
C–H
bond
functionalization
for
versatile
alkylated
polyfluoroarenes
containing
an
indene
skeleton
is
presented.
A
Pd(0)-catalyzed
three-component
cross-coupling
reaction
involving
o-bromobenzylamines,
aryl
iodides,
and
alkynes
was
developed
through
C–H
activation.
This
exhibits
excellent
regioselectivity,
selectively
forming
a
C(vinyl)–C(aryl)
bond.
The
process
yields
eight-membered
azacycles
as
the
products,
providing
straightforward
access
to
such
compounds
using
simple
substrates.
A
copper-mediated
C-H
thiolation
reaction
of
benzylamines
has
been
developed
using
a
transient
directing
group
strategy.
In
this
reaction,
picolinaldehyde
was
used
as
the
catalyst,
which
forms
imine
in
situ
with
to
facilitate
activation.
This
method
not
only
provides
straightforward
route
aryl
sulfides
but
also
represents
one
rare
examples
first-row
transition
metal-mediated
functionalization
via
approach.
The
work
highlights
potential
cost-effective
copper
catalysts
enabling
challenging
C-S
bond
formations,
advancing
field
sustainable
functionalization.
