Desymmetrization–Addition Reaction of Cyclopropenes to Imines via Synergistic Photoredox and Cobalt Catalysis
Journal of the American Chemical Society,
Год журнала:
2024,
Номер
146(28), С. 18892 - 18898
Опубликована: Июль 5, 2024
Herein,
we
designed
a
reaction
for
the
desymmetrization-addition
of
cyclopropenes
to
imines
by
leveraging
synergy
between
photoredox
and
asymmetric
cobalt
catalysis.
This
protocol
facilitated
synthesis
series
chiral
functionalized
cyclopropanes
with
high
yield,
enantioselectivity,
diastereoselectivity
(44
examples,
up
93%
yield
>99%
ee).
A
possible
mechanism
involving
cyclopropene
desymmetrization
Co-H
species
imine
addition
Co-alkyl
was
proposed.
study
provides
novel
route
important
extends
frontier
metallaphotoredox
Язык: Английский
Nickel-Catalyzed Carbonylative Negishi Cross-Coupling of Unactivated Secondary Alkyl Electrophiles with 1 atm CO Gas
Yetong Zhang,
Qihang Cao,
Yang Xi
и другие.
Journal of the American Chemical Society,
Год журнала:
2024,
Номер
146(12), С. 7971 - 7978
Опубликована: Март 14, 2024
We
describe
a
nickel-catalyzed
carbonylative
cross-coupling
of
unactivated
secondary
alkyl
electrophiles
with
the
organozinc
reagent
at
atmospheric
CO
gas,
thus
allowing
expedient
construction
unsymmetric
dialkyl
ketones
broad
functional
group
tolerance.
The
leverage
newly
developed
Язык: Английский
Recent advances in dual photoredox/nickel catalyzed alkene carbofunctionalised reactions
Anilkumar Kommoju,
Kattamuri Snehita,
K. Sowjanya
и другие.
Chemical Communications,
Год журнала:
2024,
Номер
60(68), С. 8946 - 8977
Опубликована: Янв. 1, 2024
Alkene
carbofunctionalization
reactions
have
great
potential
for
synthesizing
complex
molecules
and
constructing
structures
in
natural
products
medicinal
chemistry.
Recently,
dual
photoredox/nickel
catalysis
has
emerged
as
a
novel
strategy
alkene
carbofunctionalization.
Nickel
offers
numerous
advantages
over
other
transition
metals,
such
cost-effectiveness,
abundance,
low
toxicity,
moreover,
it
many
oxidation
states.
catalysts
exhibit
excellent
catalytic
activity
photoredox/transition
metal
catalysis,
facilitating
the
formation
of
carbon-carbon
or
carbon-heteroatom
bonds
organic
transformations.
This
review
highlights
latest
advancements
photoredox/nickel-catalyzed
carbofunctionalizations
includes
literature
published
from
2020
to
2024.
Язык: Английский
Nickel‐Catalyzed Enantioselective Decarboxylative Acylation: Rapid, Modular Access to α‐Amino Ketones**
Angewandte Chemie International Edition,
Год журнала:
2023,
Номер
62(50)
Опубликована: Ноя. 8, 2023
A
new
approach
to
the
enantiocontrolled
synthesis
of
α-amino
ketone
derivatives
is
disclosed
by
employing
a
decarboxylative
acylation
strategy.
Thus,
when
an
acyl
chloride
and
α-amido-containing
redox-active
ester
are
exposed
nickel
catalyst,
chiral
ligand,
metal
reductant,
α-amido
ketones
produced
in
good
yield
high
ee.
The
reaction
exhibits
broad
substrate
scope,
can
be
easily
scaled
up,
applied
dramatically
simplify
several
known
structures.
Язык: Английский
Cu-Catalyzed Asymmetric Three-Component Radical Acylarylation of Vinylarenes with Aldehydes and Aryl Boronic Acids
Journal of the American Chemical Society,
Год журнала:
2024,
Номер
146(47), С. 32235 - 32242
Опубликована: Ноя. 13, 2024
The
direct
use
of
readily
available
aldehydes
as
acyl
radical
precursors
has
facilitated
diverse
three-component
acylative
difunctionalization
reactions
alkenes,
offering
a
powerful
route
to
synthesize
β-branched
ketones.
However,
asymmetric
alkenes
with
still
remains
elusive.
Here
we
report
copper-catalyzed
acylarylation
vinylarenes
and
aryl
boronic
acids.
This
method
begins
formation
from
an
aldehyde
via
hydrogen
atom
transfer.
adds
the
alkene,
forming
new
benzylic
that
then
undergoes
enantioselective
arylation.
A
chiral
binaphthyl-tethered
bisoxazoline
ligand
is
essential
for
achieving
high
stereocontrol.
strategy
enables
synthesis
range
synthetically
valuable
β,β-diaryl
ketones
vinylarenes.
Язык: Английский
Nickel‐Catalyzed Regiodivergent Acylzincation of Styrenes with Organozincs and CO†
Chinese Journal of Chemistry,
Год журнала:
2023,
Номер
42(6), С. 599 - 604
Опубликована: Ноя. 2, 2023
Comprehensive
Summary
Transition
metal‐catalyzed
carbometallation
of
unsaturated
hydrocarbons
constitutes
one
the
most
efficient
synthetic
methodologies
for
construction
C—C
bond.
Recently,
incorporation
organometallic
reagent
with
CO
gas
as
a
nucleophilic
acyl
synthon
could
enable
acylmetallation
reaction,
which
greatly
increases
horizon
chemistry.
Herein,
we
report
nickel‐catalyzed
regiodivergent
acylzincation
o
‐cyano
cinnamate
ester
and
styrene,
in
cyano
moiety
intramolecularly
captures
zinc
intermediates
to
trigger
tandem
cyclization
process.
This
protocol
features
mild
conditions,
broad
substrate
scope
excellent
functional
group
tolerance,
thus
affording
diverse
array
highly
functionalized
carbocyclic
compounds.
Язык: Английский
Exploration of Quinim Ligand in Ni-Catalyzed Enantioselective Reductive Carbamoyl-Alkylation of Alkene
Chinese Journal of Organic Chemistry,
Год журнала:
2023,
Номер
43(12), С. 4239 - 4239
Опубликована: Янв. 1, 2023
Язык: Английский
Nickel/Titanocene-Catalyzed Electrophilic Acylation Coupling of Styrene Oxides
Organic Letters,
Год журнала:
2023,
Номер
25(38), С. 6959 - 6963
Опубликована: Сен. 20, 2023
The
cross-coupling
of
epoxides
with
acyl
chlorides
or
anhydrides
by
a
nickel/titanocene
dual
catalytic
system
is
established.
A
variety
synthetically
useful
β-hydroxy
ketones
were
obtained
in
good
to
high
yields
using
modified
pyridine-oxazoline
ligand.
reaction
proceeds
via
the
cooperation
titanocene-catalyzed
ring-opening
and
nickel-catalyzed
acylation
benzylic
radical
intermediate.
Язык: Английский
Nickel‐Catalyzed Enantioselective Decarboxylative Acylation: Rapid, Modular Access to α‐Amino Ketones**
Angewandte Chemie,
Год журнала:
2023,
Номер
135(50)
Опубликована: Ноя. 8, 2023
Abstract
A
new
approach
to
the
enantiocontrolled
synthesis
of
α‐amino
ketone
derivatives
is
disclosed
by
employing
a
decarboxylative
acylation
strategy.
Thus,
when
an
acyl
chloride
and
α‐amido‐containing
redox‐active
ester
are
exposed
nickel
catalyst,
chiral
ligand,
metal
reductant,
α‐amido
ketones
produced
in
good
yield
high
ee.
The
reaction
exhibits
broad
substrate
scope,
can
be
easily
scaled
up,
applied
dramatically
simplify
several
known
structures.
Язык: Английский
Ni-Catalyzed Enantioselective Decarboxylative Acylation: Rapid, Modular Access to a-Amino Ketones
Опубликована: Сен. 13, 2023
A
new
approach
to
the
enantiocontrolled
synthesis
of
alpha-amino
ketone
derivatives
is
disclosed
by
employing
a
decarboxylative
acylation
strategy.
Thus,
when
an
acyl
chloride
and
alpha-amido-containing
redox-active
ester
are
exposed
Ni-catalysis,
chiral
ligand,
metal
reductant,
alpha-amido
ketones
produced
in
good
yield
high
ee.
The
reaction
exhibits
broad
substrate
scope,
can
be
easily
scaled
up,
applied
dramatically
simplify
several
known
structures.
Язык: Английский