Advanced Science,
Journal Year:
2024,
Volume and Issue:
unknown
Published: July 5, 2024
A
Pd-catalyzed
enantioselective
aminosilylation
of
alkenes
via
tandem
Aza-Heck/silylation
reaction
under
Pd/Sadphos
catalysis
is
disclosed.
wide
array
oxime
esters
and
silicon
reagents
are
tolerated,
furnishing
the
chiral
pyrrolines
bearing
one
quaternary
or
two
contiguous
stereocenters
in
good
yield
with
high
enantioselectivity.
Not
only
terminal
but
also
tri-substituented
internal
successfully
participate
reaction,
delivering
vicinal
complete
diastereoselectivity
DFT
study
conducted
to
probe
pathway
origin
enantioselectivity,
which
revealed
that
stereoinduction
arises
from
weak
interaction
between
aromatic
ring
substrate
fragment
naphthyl
group
ligand.
Organic Letters,
Journal Year:
2023,
Volume and Issue:
25(20), P. 3664 - 3669
Published: May 12, 2023
Here,
a
palladium-catalyzed
photoinduced
N-to-alkyl
radical
relay
Heck
reaction
of
o-alkylbenzamides
at
benzylic
sites
with
vinyl
arenes
is
described.
The
employs
neither
exogeneous
photosensitizers
nor
external
oxidants.
It
proposed
to
proceed
via
hybrid
palladium-radical
mechanism
which
occurs
under
mild
conditions
that
are
compatible
wide
range
functional
groups.
products
easily
transformed
azepinone
derivatives,
prevalent
in
pharmaceuticals
and
natural
products.
Chemistry - A European Journal,
Journal Year:
2024,
Volume and Issue:
30(26)
Published: Feb. 13, 2024
Abstract
Transition–metal
catalyzed
tandem
asymmetric
reactions
were
powerful
tools
to
access
various
chiral
compounds.
Many
strategies
have
been
developed
for
the
coupling
of
1,n‐dienes
with
aryl
halides
via
a
Heck/Tsuji–Trost
process.
However,
control
regio‐
and
stereo‐chemistry
remains
challenging
task.
This
minireview
details
recent
advances
in
field
by
palladium
complex,
which
opened
new
opportunities
expanded
our
understanding
this
area
research
years.
ACS Catalysis,
Journal Year:
2024,
Volume and Issue:
14(3), P. 1575 - 1583
Published: Jan. 16, 2024
The
example
of
iron-catalyzed
reductive
fluoroalkylalkenylation
unactivated
alkenes
has
been
disclosed,
affording
the
stereodefined
homoallylic
fluoroalkanes
with
high
efficiency
and
regioselectivity.
This
three-component
cross-electrophile
coupling
features
directing
groups
free,
good
functional
group
tolerance,
broad
substrate
scope,
late-stage
difunctionalization
biorelevant
molecules.
Moreover,
this
protocol
sheds
light
on
distinct
reactivity
disparities
between
fluoroalkyl
nonfluoroalkyl
radicals
in
cross-coupling
reactions,
highlighting
unique
nature
iron/B2pin2
systems.
Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(12), P. 2354 - 2358
Published: March 15, 2024
We
herein
disclose
a
novel
palladium-catalyzed
1,2-alkynylarylation
of
vinyl
arenes
using
haloalkynes
and
arylboronic
acids
as
coupling
partners.
This
reaction
is
characterized
by
broad
substrate
scope,
controllable
sequence,
excellent
chemo-
regioselectivities.
Mechanistic
investigations
suggest
that
the
initiated
regioselective
insertion
into
alkynyl-Pd(II)
species,
silver
salt
crucial
for
this
transformation,
serving
both
Lewis
acid
halide
scavenger.
protocol
provides
efficient
access
to
new
carbon
skeletons,
which
are
embedded
in
key
biologically
active
motifs.
Journal of the American Chemical Society,
Journal Year:
2022,
Volume and Issue:
144(50), P. 22877 - 22883
Published: Dec. 12, 2022
As
a
general
method
for
the
synthesis
of
alcohols,
direct
oxygenation
alkenes
is
difficult
to
afford
linear
alcohols.
Herein,
we
communicate
remote
hydro-oxygenation
under
palladium
catalysis,
in
which
both
terminal
and
internal
are
suitable
yield
corresponding
alcohols
efficiently.
A
compatible
SelectFluor/silane
redox
system
plays
an
essential
role
excellent
chemo-
regioselectivities.
The
reaction
features
broad
substrate
scope
functional
group
compatibility.
The Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
89(1), P. 216 - 223
Published: Dec. 18, 2023
The
C–N
bond
transamidation
of
primary
amides
with
N,N-dimethyl
enaminones
has
been
efficiently
realized
by
heating
in
the
presence
trifluoromethanesulfonic
acid
(TfOH).
method
enables
practical
synthesis
valuable
enamides
without
use
any
metal
reagent.
In
addition,
this
protocol
can
also
be
expanded
to
reactions
sulfonamides,
and
late-stage
functionalization
on
sulfonamide
drugs
such
as
Celecoxib
Valdecoxib
verified.
Moreover,
participation
water
assisting
process
identified
isotope
labeling
experiments
using
D2O,
disclosing
a
new
possibility
designing
catalytic
tactic
other
reactions.
Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(32), P. 6809 - 6813
Published: Aug. 5, 2024
Represented
herein
is
the
first
1,3-difunctionalization
of
alkenes
via
photocatalysis.
A
single
cobaloxime
used
to
carry
out
two
catalytic
cycles
in
which
not
only
as
a
photocatalyst
initiate
reaction
but
also
metal
catalyst
for
β-H
elimination
process.
Electron-deficient
alkenes,
electron-rich
and
unactivated
could
be
directly
converted
1,3-bisphosphorylated
products,
even
unsymmetric
with
H
Organic Letters,
Journal Year:
2023,
Volume and Issue:
25(15), P. 2701 - 2706
Published: April 10, 2023
Catalytic
1,1-difunctionalization
of
unactivated
alkenes
with
two
nucleophiles
has
attracted
a
great
deal
interest
but
remains
challenge
in
synthetic
chemistry.
Here,
palladium(II)-catalyzed
Nu/Nu'-type
1,1-oxamidation
and
1,1-diamination
alkenyl
carbonyl
compounds
followed
by
amination
are
described.
The
distinguishing
features
this
reaction
include
the
lack
directing
group,
good
functional
group
tolerance,
easily
operational
catalytic
conditions.
Mechanistic
investigations
support
unique
route
involving
consecutive
nucleopalladations
for
1,1-difunctionalization.
