Nickel-catalyzed cross-electrophile couplings of aryl fluorosulfates with vinyl chlorosilanes
Jin-He Na,
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Hong-Jian Du,
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Jia-Wen Jing
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et al.
Journal of Catalysis,
Journal Year:
2024,
Volume and Issue:
437, P. 115636 - 115636
Published: July 6, 2024
Language: Английский
Cross-Electrophile Silylation of Aryl Carboxylic Esters with Hydrochlorosilanes by SiH-Directed and Cr-Catalyzed Couplings
ACS Catalysis,
Journal Year:
2023,
Volume and Issue:
13(18), P. 12062 - 12073
Published: Aug. 29, 2023
The
formation
of
silicon–carbon
bonds
through
the
selective
coupling
two
strong
electrophilic
has
been
less
developed.
We
report
here
silylation
reactions
that
proceed
by
Si–Cl/C–O
in
a
process
is
promoted
chromium
catalysis
via
α-agostic
SiH
→
Cr
interactions,
allowing
Si–C
under
ambient
conditions.
occur
inexpensive
hydrochlorosilanes
with
unactivated
aryl
carboxylic
esters
to
give
arylated
hydrosilanes,
while
suppressing
side
hydride-mediated
reduction
achieving
high
chemoselectivity.
In
addition
monosilylation,
both
geminal
Si–Cl
hydrodichlorosilanes
couple
C–O
smoothly
afford
and
achieve
double
silylations.
disilanes
diesters
also
described.
Experimental
theoretical
studies
suggest
initiates
reaction
hydrochlorosilane
Cr,
which
interaction
group
stabilizes
related
intermediate
transition
state,
leading
cleavage
bond
low
barrier
silachromate.
Further
breaking
an
occurs
along
agostic
interaction,
may
serve
as
rate-determining
step
silylation.
observation
normal
second-order
kinetic
isotope
effect
indicates
on
rates
coupling.
Because
reactive
groups
are
retained
silylation,
approach
provides
viable
strategy
access
tetraorganosilane
motifs
late-stage
hydrofunctionalization.
Language: Английский
Palladium‐Catalyzed Cyclization/Alkenylation of Ynone Oximes with Vinylsilanes for the Assembly of Isoxazolyl Vinylsilanes
Jianxiao Li,
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Chenjing Hong,
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Yanan Niu
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et al.
Chemistry - An Asian Journal,
Journal Year:
2024,
Volume and Issue:
19(6)
Published: Jan. 15, 2024
Abstract
A
palladium‐catalyzed
cascade
cyclization/alkenylation
for
the
assembly
of
synthetically
valuable
isoxazolyl
vinylsilane
derivative
has
been
accomplished.
Easily
accessible
ynone
oximes,
and
available
agents
were
used
as
reaction
starting
materials
This
protocol
features
broad
substrate
scope,
good
functional
group
tolerance,
step‐
atom‐economy.
Remarkably,
this
approach
provides
a
new
construction
structurally
diverse
isoxazolyl‐containing
vinylsilanes
with
high
molecular
complexity,
showing
promising
application
in
synthetic
pharmaceutical
chemistry.
Language: Английский
Cobalt-catalyzed cross-electrophile coupling of alkynyl sulfides with unactivated chlorosilanes
Donghui Xing,
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Jinlin Liu,
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D. Cai
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et al.
Nature Communications,
Journal Year:
2024,
Volume and Issue:
15(1)
Published: May 27, 2024
Abstract
Herein,
we
disclose
a
highly
efficient
cobalt-catalyzed
cross-electrophile
alkynylation
of
broad
range
unactivated
chlorosilanes
with
alkynyl
sulfides
as
stable
and
practical
electrophiles.
Strategically,
employing
easily
synthesized
precursors
allows
access
to
various
alkynylsilanes
in
good
excellent
yields.
Notably,
this
method
avoids
the
utilization
strong
bases,
noble
metal
catalysts,
high
temperature
forcing
reaction
conditions,
thus
presenting
apparent
advantages,
such
substrate
scope
(72
examples,
up
97%
yield),
Csp-S
chemo-selectivity
functional
group
compatibility
(Ar-X,
X
=
Cl,
Br,
I,
OTf,
OTs).
Moreover,
utilities
are
also
illustrated
by
downstream
transformations
late-stage
modification
structurally
complex
natural
products
pharmaceuticals.
Mechanistic
studies
elucidated
that
cobalt
catalyst
initially
reacted
sulfides,
activation
occurred
via
an
S
N
2
process
instead
radical
pathway.
Language: Английский
Aliphatic Hydrosilanes via Nickel-Catalyzed Reductive Csp3–Si Coupling of Primary Alkyl Bromides and Chlorohydrosilanes
Xiao‐Xue Wei,
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Zhenzhen Zhao,
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Xiaobo Pang
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et al.
Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(29), P. 6125 - 6129
Published: July 12, 2024
The
reductive
C-Si
coupling
of
chlorosilanes
offers
efficient
access
to
organosilanes,
but
its
potential
for
constructing
aliphatic
ones
remains
largely
unexplored.
This
manuscript
presents
a
nickel-catalyzed
Csp
Language: Английский
Nickel-Catalyzed Cross-Electrophile Vinylation of α-Chloro Phosphonates
Liang Zou,
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Huimin Yang,
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Tian Xie
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et al.
The Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
89(21), P. 15822 - 15833
Published: Oct. 18, 2024
Herein,
we
report
a
general
and
efficient
Ni-catalyzed
reductive
cross-coupling
reaction
of
substituted
vinyl
bromides
α-chloro
phosphonates
to
access
set
α-vinyl
using
zinc
as
the
terminal
reductant.
This
exhibits
broad
substrate
adaptability
good
functional
group
tolerance,
which
allows
afford
diverse
compounds
including
structurally
complex
motifs
from
natural
products
drugs.
Furthermore,
practicality
was
certificated
through
gram-scale
transformation
experiments.
The
preliminary
mechanistic
investigations
support
radical
chain
process.
potential
realize
enantiomeric
control
makes
it
more
valuable
for
further
exploration.
Language: Английский
Cobalt-Catalyzed Cross-Electrophile Coupling of Alkynyl Sulfides with Unactivated Chlorosilanes
Research Square (Research Square),
Journal Year:
2024,
Volume and Issue:
unknown
Published: Jan. 29, 2024
Abstract
Herein,
we
disclose
a
highly
efficient
cobalt-catalyzed
cross-electrophile
alkynylation
of
broad
range
unactivated
chlorosilanes
with
alkynyl
sulfides.
Strategically,
employing
stable
and
easily
synthesized
sulfides
as
precursors
allows
access
to
various
alkynylsilanes
in
good
excellent
yields.
Notably,
this
method
avoids
the
utilization
strong
bases,
noble
metal
catalysts,
high
temperature
forcing
reaction
conditions,
thus
presents
apparent
advantages,
such
substrate
scope
(72
examples,
up
97%
yield),
Csp-S
chemo-selectivity
functional
group
compatibility
(Ar-X,
X
=
Cl,
Br,
I,
OTf,
OTs).
Moreover,
utilities
are
also
illustrated
by
downstream
transformations
late-stage
modification
structurally
complex
natural
products
pharmaceuticals.
Mechanistic
studies
elucidated
that
cobalt
catalyst
initially
reacted
sulfides,
activation
occurred
via
an
S
N2
process
instead
radical
pathway.
Language: Английский
Electroreductive Cross-Coupling between Aromatic Aldehydes and Chlorosilanes Enabling the Synthesis of α-Silyl Alcohols
Fen Han,
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Qian Su,
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Yu Li
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et al.
Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(33), P. 7037 - 7042
Published: Aug. 14, 2024
α-Silyl
alcohols
are
powerful
structural
motifs
for
pharmaceutical
chemistry,
materials
and
organic
synthesis.
The
limitations
of
current
synthetic
techniques
encompass
a
requirement
difficult-to-obtain
silyl
precursors,
noble-metal
catalysts,
narrow
substrate
scopes.
Here,
we
developed
general
method
α-silyl
through
electroreductive
cross-coupling
aldehydes
chlorosilane.
This
features
easily
available
reagents,
mild
conditions,
wide
scope.
establishment
this
protocol
will
provide
an
alternative
access
to
alcohols.
Language: Английский
Nickel-catalyzed stereospecific reductive cross-coupling of vinyl chlorosilanes with axially chiral biaryl electrophiles
Tiantian Yin,
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Shiyuan Sui,
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Shuqi Li
No information about this author
et al.
Chemical Communications,
Journal Year:
2024,
Volume and Issue:
60(96), P. 14204 - 14207
Published: Jan. 1, 2024
Nickel-catalyzed
stereospecific
reductive
cross-coupling
of
vinyl
chlorosilanes
with
chiral
biaryl
electrophiles
for
the
synthesis
axially
organosilanes.
Language: Английский