Chiral dinitrogen ligand enabled asymmetric Pd/norbornene cooperative catalysis toward the assembly of C–N axially chiral scaffolds
Nature Communications,
Год журнала:
2024,
Номер
15(1)
Опубликована: Июнь 8, 2024
Abstract
C
−
N
axially
chiral
compounds
have
recently
attracted
significant
interest
among
synthetic
chemistry
community
due
to
their
widespread
application
in
pharmaceuticals,
advanced
materials
and
organic
synthesis.
Although
the
emerging
asymmetric
Catellani
reaction
offers
great
opportunity
for
modular
efficient
preparation,
only
operative
NBE
strategy
date
requires
using
half
stoichiometric
amount
of
2,6-disubstituted
bromoarenes
as
electrophiles.
We
herein
report
an
assembly
C–N
scaffolds
through
a
distinct
ligand
strategy.
The
crucial
source,
biimidazoline
(BiIM)
dinitrogen
ligand,
is
used
relatively
low
loading
permits
use
less
bulky
bromoarenes.
method
also
features
feedstock
plain
NBE,
high
reactivity,
good
enantioselectivity,
ease
operation
scale-up.
Applications
preparation
optoelectronic
material
candidates
featuring
two
axes
C–H
activation
been
demonstrated.
Язык: Английский
Catalytic ortho C–H methylation and trideuteromethylation of arylthianthrenium salts via the Catellani strategy
Organic Chemistry Frontiers,
Год журнала:
2024,
Номер
11(12), С. 3333 - 3340
Опубликована: Янв. 1, 2024
We
report
a
Pd/NBE
cooperative
catalyzed
ortho
C–H
methylation
and
trideuteromethylation
of
arylthianthrenium
salts,
enabling
the
efficient
synthesis
wide
variety
(trideutero)methylated
arenes
in
moderate
to
good
yields.
Язык: Английский
Solvent‐Controlled Enantiodivergent Construction of P(V)‐Stereogenic Molecules via Palladium‐Catalyzed Annulation of Prochiral N‐Aryl Phosphonamides with Aromatic Iodides
Qingyu Tian,
Jin Ge,
Yaopeng Liu
и другие.
Angewandte Chemie International Edition,
Год журнала:
2024,
Номер
63(41)
Опубликована: Июль 9, 2024
In
this
work,
we
describe
an
efficient
and
modular
method
for
enantiodivergent
accessing
P(V)-stereogenic
molecules
by
utilizing
the
catalytic
atroposelective
Catellani-type
C-H
arylation/desymmetric
intramolecular
N-arylation
cascade
reaction.
The
enantioselectivity
of
protocol
was
proved
to
be
tuned
polarity
solvent,
thus
providing
a
wide
range
both
chiral
enantiomers
in
moderate
good
yields
with
excellent
enantiomeric
excesses.
Noteworthy
is
that
strategy
developed
herein
represents
unprecedented
example
solvent-dictated
inversion
compounds.
Язык: Английский
Modular Synthesis of Polysubstituted α-Phosphorylated Arenes via the Catellani Strategy
Organic Letters,
Год журнала:
2024,
Номер
26(27), С. 5770 - 5775
Опубликована: Июнь 28, 2024
In
this
paper,
we
described
a
palladium/norbornene-catalyzed
Язык: Английский
Catalytic Ortho C-H Methylation and Trideuteromethylation of Ar-ylthianthrenium Salts via the Catellani Strategy
Опубликована: Фев. 26, 2024
We
reported
a
Pd/NBE
cooperative
catalyzed
ortho
C−H
methylation
and
trideuteromethylation
of
arylthianthrenium
salts,
enabling
the
efficient
synthesis
wide
variety
(trideutero)methylated
arenes
in
moderate
to
good
yields.
The
method
demonstrates
excel-lent
tolerance
towards
functional
groups,
scalability,
potential
extension
late-stage
functionalization
biorelevant
mole-cules.
In
combined
with
thianthrenation
arenes,
this
approach
provides
an
effective
for
site-selective
(trideutero)methylation
arenes.
Additionally,
reaction
represents
first
example
Catellani
involving
aryl
sul-fonium
salts.
Язык: Английский
Solvent‐Controlled Enantiodivergent Construction of P(V)‐Stereogenic Molecules via Palladium‐Catalyzed Annulation of Prochiral N‐Aryl Phosphonamides with Aromatic Iodides
Qingyu Tian,
Jin Ge,
Yaopeng Liu
и другие.
Angewandte Chemie,
Год журнала:
2024,
Номер
136(41)
Опубликована: Июль 9, 2024
Abstract
In
this
work,
we
describe
an
efficient
and
modular
method
for
enantiodivergent
accessing
P(V)‐stereogenic
molecules
by
utilizing
the
catalytic
atroposelective
Catellani‐type
C−H
arylation/desymmetric
intramolecular
N
‐arylation
cascade
reaction.
The
enantioselectivity
of
protocol
was
proved
to
be
tuned
polarity
solvent,
thus
providing
a
wide
range
both
chiral
enantiomers
in
moderate
good
yields
with
excellent
enantiomeric
excesses.
Noteworthy
is
that
strategy
developed
herein
represents
unprecedented
example
solvent‐dictated
inversion
compounds.
Язык: Английский
Palladium-Catalyzed Enantioselective Synthesis of P(V)-Stereogenic Compounds via Desymmetric Annulation of Prochiral Phosphinamides and Aryl Iodides
Qingyu Tian,
Jin Ge,
Yaopeng Liu
и другие.
Organic Letters,
Год журнала:
2024,
Номер
27(1), С. 121 - 128
Опубликована: Дек. 30, 2024
The
enantioselective
synthesis
of
P(V)-stereogenic
compounds
has
emerged
as
an
interesting
research
topic
primarily
due
to
their
significant
biological
activity
and
broad
application
prospects.
Herein,
we
disclose
a
method
for
the
construction
from
prochiral
phosphinamides
aryl
iodides
via
palladium-
chiral
norbornene-catalyzed
desymmetric
annulation.
were
formed
with
scope
excellent
enantiomeric
excesses.
It
is
noteworthy
that
synthetic
value
this
procedure
was
proven
by
variety
transition
metal-catalyzed
cross-coupling
reactions
using
C–Br
bond
on
product
versatile
linchpin
electrophile.
Язык: Английский