ACS Catalysis,
Journal Year:
2022,
Volume and Issue:
13(1), P. 744 - 748
Published: Dec. 23, 2022
Herein,
we
report
a
cobalt-catalyzed
asymmetric
reductive
1,2-dicarbofunctionalization
of
1,3-dienes
employing
o-bromoaryl
imines
as
bis-electrophilic
coupling
partner.
This
method
provides
an
entry
to
prepare
disubstituted
cis-indanes
in
high
diastereo-
and
enantioselectivities
under
mild
reaction
conditions.
The
proposed
mechanism
consists
enantioselective
intermolecular
migratory
insertion
diastereoselective
intramolecular
allylation
the
key
elementary
steps.
Organic & Biomolecular Chemistry,
Journal Year:
2021,
Volume and Issue:
19(26), P. 5673 - 5701
Published: Jan. 1, 2021
Intramolecular
carbometallation-initiated
asymmetric
transformations
are
a
general
and
powerful
approach
for
the
construction
of
carbo-
heterocyclic
systems
with
one
more
stereocenters.
In
addition,
newly
developed
multiple
cascade
reactions
an
attractive
strategy
increasing
molecular
complexity
in
step.
recent
years,
great
progress
has
been
made
this
area
use
various
palladium
nickel
complexes
P-
N-donor
chiral
ligands.
This
review
highlights
developments
intramolecular
Heck
reactions,
reductive
types
(intramolecular
Heck/Heck,
Heck/nucleophilic
trapping,
Heck/Tsuji-Trost,
Heck/Suzuki-Miyaura,
Heck/Sonogashira,
Heck/carbonylation)
synthesis
complex
molecules
over
past
5
years.
A
number
examples
from
before
2016
included
as
background
information.
Particular
attention
is
paid
to
inexpensive
highly
efficient
catalysts
considered
here.
perspective
on
current
challenges
potential
future
field
type
cyclizations
also
provided.
Chemistry - A European Journal,
Journal Year:
2021,
Volume and Issue:
27(28), P. 7657 - 7662
Published: April 8, 2021
Abstract
A
novel
asymmetric
nickel‐based
procedure
has
been
developed
in
which
CO
2
fixation
is
achieved
as
a
second
step
of
truncated
Heck
coupling.
For
this,
new
chiral
ligand
prepared
and
shown
to
achieve
enantiomeric
excesses
up
99
%.
The
overall
process
efficiently
furnishes
2,3‐dihydrobenzofuran‐3‐ylacetic
acids,
an
important
class
bioactive
products,
from
easy
prepare
starting
materials.
combined
experimental
computational
effort
revealed
the
key
steps
catalytic
cycle
suggested
unexpected
participation
Ni(I)
species
coupling
event.
Angewandte Chemie International Edition,
Journal Year:
2022,
Volume and Issue:
61(11)
Published: Jan. 19, 2022
We
have
developed
a
nickel-catalyzed
desymmetric
reductive
cyclization/coupling
of
1,6-dienes.
The
reaction
provides
an
efficient
method
for
constructing
chiral
tertiary
alcohol
and
quaternary
stereocenter
by
single
operation.
has
excellent
diastereoselectivity
high
enantioselectivity,
broad
substrate
scope,
as
well
good
tolerance
functional
groups.
Preliminary
mechanism
studies
show
that
alkyl
nickel(I)
species
are
involved
in
the
reaction.
Angewandte Chemie International Edition,
Journal Year:
2022,
Volume and Issue:
61(36)
Published: July 12, 2022
Herein,
we
leverage
the
Ni-catalyzed
enantioselective
reductive
dicarbofunctionalization
of
internal
alkenes
with
alkyl
iodides
to
enable
synthesis
chiral
pyrrolidinones
bearing
vicinal
stereogenic
centers.
The
application
newly
developed
Chinese Journal of Organic Chemistry,
Journal Year:
2022,
Volume and Issue:
42(10), P. 3302 - 3302
Published: Jan. 1, 2022
Alkenes
are
cheap
and
easily
available
bulk
industrial
feedstocks.Difunctionalization
of
alkenes
can
rapidly
construct
complex
molecules,
which
have
broad
applications
in
organic
synthesis.Compared
with
traditional
redox-neutral
alkene
difunctionalization,
the
reductive
difunctionalization
introduce
two
different
electrophiles
to
both
sides
carbon-carbon
double
bond,
has
advantages
mild
reaction
conditions,
high
functional
group
tolerance,
no
need
for
pre-prepared
organometallic
reagents.The
latest
research
progress
nickel-catalyzed
is
summarized.The
development
prospect
prospected.
ACS Catalysis,
Journal Year:
2023,
Volume and Issue:
13(10), P. 6795 - 6803
Published: May 3, 2023
Herein,
we
report
a
nickel-catalyzed
asymmetric
three-component
trans-dicarbofunctionalization
of
β-substituted
α-naphthyl
propargylic
alcohols
using
readily
available
aryl
and
benzyl
halides
as
the
coupling
partners
under
reductive
conditions.
This
cross-electrophile
strategy
enables
synthesis
various
axially
chiral
allylic
bearing
tetrasubstituted
olefinic
unit
in
complete
regio-
E
selectivity,
well
high
enantiocontrol.
Relying
on
hydroxyl
group
functional
handle,
such
structural
motifs
are
successfully
derivatized
into
diverse
functional-group-rich
alkenes.
Nature Communications,
Journal Year:
2023,
Volume and Issue:
14(1)
Published: Nov. 30, 2023
Alkene
dicarbofunctionalization
is
an
efficient
strategy
and
operation-economic
fashion
for
introducing
complexity
in
molecules.
A
nickel/photoredox
dual
catalyzed
arylalkylation
of
nonactivated
alkenes
the
simultaneous
construction
one
C(sp3)-C(sp3)
bond
C(sp3)-C(sp2)
has
been
developed.
The
mild
catalytic
method
provided
valuable
indanethylamine
derivatives
with
wide
substrate
scope
good
functional
group
compatibility.
An
enantioselective
was
also
achieved
pyridine-oxazoline
as
a
ligand.
efficiency
metallaphotoredox
demonstrated
concise
synthesis
pharmaceutically
active
compounds.
Synlett,
Journal Year:
2020,
Volume and Issue:
31(19), P. 1843 - 1850
Published: July 27, 2020
The
merger
of
cross-electrophile
coupling
and
asymmetric
catalysis
provides
a
novel
approach
to
the
preparation
optically
active
compounds.
This
method
is
often
endowed
with
high
step
economy,
mild
conditions,
excellent
tolerance
functional
groups.
Recent
advances
in
research
field
nickel-catalyzed
reactions
are
highlighted
this
concise
Synpacts
article.
1
Introduction
2
Asymmetric
Cross-Electrophile
Coupling
Reactions
between
Organohalides
3
Electrophilic
Ring-Opening
4
Difunctionalization
Alkenes
4.1
Two-Component
Involving
Arylnickelation
as
an
Enantiodetermining
Step
4.2
Carbamoylnickelation
4.3
Three-Component
5
Functionalization
Carbonyl
Compounds
6
Summary
Angewandte Chemie International Edition,
Journal Year:
2020,
Volume and Issue:
60(6), P. 2828 - 2832
Published: Nov. 3, 2020
Nickel-catalyzed
intermolecular
Heck
reaction
of
cycloalkenes
proceeds
well
with
aryl
triflates,
mesylates
and
tosylates
in
excellent
enantiomeric
ratios.
The
asymmetric
reductive
also
works
a
2-cyclopentenone
ketal,
which
is
equivalent
to
conjugate
arylation
the
enone
itself.
Organic Letters,
Journal Year:
2020,
Volume and Issue:
22(22), P. 8829 - 8835
Published: Oct. 29, 2020
Herein,
we
present
a
nickel-catalyzed
three-component
reductive
alkylacylation
of
electron-deficient
activated
alkenes
with
tertiary
alkyl
bromides
and
acid
anhydrides.
This
method
enables
the
efficient
preparation
variety
ketones
broad
substrate
scope
high
functionality
tolerance
starting
from
simple
precursors.
On
basis
preliminary
mechanistic
investigations,
catalytic
cycle
involving
synergistic
interaction
nickel,
zinc,
MgCl2
is
proposed
as
major
reaction
pathway.
