The Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
unknown
Published: Nov. 19, 2024
Herein,
a
cobalt-catalyzed
intramolecular
enantioselective
reductive
Heck
reaction
is
disclosed.
Starting
from
N-ortho-iodoaryl-2-(trifluoromethyl)acrylamides,
plethora
of
chiral
oxindoles
bearing
trifluoromethylated
quaternary
stereogenic
centers
at
the
C3-position
are
achieved
in
moderate
to
good
yields
(up
88%
yield)
and
excellent
enantioselectivities
94%
ee)
by
employing
zinc/silane
as
reducing
agent.
Other
than
trifluoromethyl
group,
number
alkyl,
aryl,
ester
groups
were
also
obtained
albeit
relatively
lower
(68–78%
ee).
European Journal of Organic Chemistry,
Journal Year:
2022,
Volume and Issue:
26(3)
Published: Dec. 9, 2022
Abstract
Palladium
catalysis
enables
efficient
and
versatile
domino
reactions
that
are
initiated
by
an
intramolecular
Mizoroki‐Heck
reaction
then
terminated
a
Suzuki‐Miyaura
coupling.
The
stereochemistry
of
this
cascade
is
concerned
under
three
aspects:
Firstly,
as
stereoselective
formation
carbon−carbon‐double
bonds,
when
the
initial
carbometalation
occurs
at
alkyne
moiety.
Secondly
diastereoselective
thirdly
enantioselective
stereogenic
carbon
centers
Heck
step
directed
to
alkene
Valuable
protocols
lead
–
otherwise
not
easily
accomplished
stereo
control
in
tri‐
tetra‐substituted
double
bonds
according
first
conception.
versions
permit
multiple
stereocenters
mono‐
polycycles.
Enantioselective
were
developed
only
recently.
fact
newly
created
highly‐substituted,
tertiary
or
quaternary
ones,
makes
methods
presented
review
useful
tools
synthesis.
ChemistrySelect,
Journal Year:
2023,
Volume and Issue:
8(27)
Published: July 17, 2023
Abstract
Metal
nanoparticles
immobilized
in
the
confined
space
are
a
catalogue
of
efficient
and
widely
used
catalysts.
Herein
we
develop
gel‐based
bimetallic
nanoparticle
catalytic
system
with
different
ratios
Pd/Cu
NPs
by
wet
impregnation
reduction
using
stable
covalent
gel
(triazole‐A1B1)
as
porous
support.
Triazole‐A1B1
is
synthesized
from
1,4‐diazidobenzene
(A1)
tetrakis(4‐ethynylphenyl)methane
(B1)
via
Cu(I)‐catalyzed
azide‐alkyne
clcloaddition.
The
metal
highly
dispersed
uniformly
distributed
an
average
particle
size
distribution
2.06–3.29
nm.
Cu/Pd@A1B1
shows
high
efficiency
catalyzing
Sonogashira‐Hagihara
Mizoroki‐Heck
coupling
reactions.
introduction
oxygenophilic
Cu
effectively
improves
activity
system.
In
addition,
Cu1Pd2@A1B1
good
reusability.
Especially,
it
can
be
reused
five
times
maintains
without
significant
deactivation
reaction.
Advanced Synthesis & Catalysis,
Journal Year:
2024,
Volume and Issue:
366(15), P. 3367 - 3371
Published: June 14, 2024
Abstract
Palladium‐catalyzed
thioesterification
of
(aza)indole‐tethered
aryl
iodides,
Mo(CO)
6
,
and
sulfonyl
chlorides
is
reported.
A
series
C2
thioester‐group
substituted
indoline‐fused
ring
compounds
are
constructed
by
an
intramolecular
Heck
cyclization
carbonylation
chemistry
involving
N
‐(2‐iodobenzoyl)indole.
The
salient
features
this
three‐component
cascade
sequence
include
the
use
solid
as
carbon
monoxide
source
good
functional
group
tolerance.
Organic Letters,
Journal Year:
2023,
Volume and Issue:
25(45), P. 8139 - 8144
Published: Nov. 7, 2023
A
Pd-catalyzed
intramolecular
dearomative
[4
+
2]
cycloaddition
reaction
of
naphthalenes
with
arylalkynes
is
developed.
The
protocol
provides
a
straightforward
method
to
access
range
polycyclic
dihydronaphthalenes
containing
two
vicinal
all-carbon
stereocenters
in
moderate
yields
under
mild
conditions
an
air
atmosphere.
deuterium
labeling
experiment
suggests
pathway
involving
electrophilic
dearomatization
followed
by
Friedel–Crafts
cyclization.
Several
synthetic
transformations
the
product
were
conducted
demonstrate
utility
this
reaction.
Current Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
27(2), P. 71 - 92
Published: Jan. 1, 2023
Abstract:
This
review
updates
the
field
of
asymmetric
cascade
palladium
catalysis
applied
to
synthesis
chiral
heterocycles
since
2019.
It
illustrates
how
much
a
diversity
catalysts
promote
unprecedented
domino
reactions
many
types,
allowing
direct
access
wide
variety
complex
and
densely
functionalized
heterocyclic
molecules.
Organic Chemistry Frontiers,
Journal Year:
2024,
Volume and Issue:
11(6), P. 1736 - 1741
Published: Jan. 1, 2024
A
double
Heck
and
Heck–Suzuki
cascade
approach
using
Pd
catalyst
yields
trifluoromethyl-tethered
3,3-disubstituted
oxindoles
from
N
-(
o
-bromoaryl)
trifluoromethyl
acrylamide
with
alkenes/phenylboronic
acids.
Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(11), P. 2175 - 2179
Published: March 7, 2024
The
Heck/Suzuki
tandem
reaction
has
emerged
as
an
essential
strategy
for
the
synthesis
of
complex
molecules.
Herein,
efficient
palladium-catalyzed
(Z)-1-iodo-1,6-dienes
with
organoboronic
acids
is
described,
providing
various
tetrahydropyridines
in
good
to
excellent
yields
under
mild
conditions.
key
success
this
approach
avoidance
intramolecular
second
Heck
insertion
occurring
prior
transmetalation
step.
In
addition,
asymmetric
version
investigated
deliver
chiral
tetrahydropyridine
yield
promising
enantioselectivity.
Chemical Communications,
Journal Year:
2024,
Volume and Issue:
60(28), P. 3858 - 3861
Published: Jan. 1, 2024
A
copper-catalyzed
intramolecular
dearomative
amination
of
indoles
via
a
formal
aza-Wacker
reaction
is
described,
affording
polycyclic
indolines
bearing
exocyclic
CC
bonds
in
moderate
to
excellent
yields
with
molecular
oxygen
as
an
oxidant.
