Angewandte Chemie,
Journal Year:
2022,
Volume and Issue:
135(10)
Published: Dec. 28, 2022
Abstract
We
describe
here
the
development
of
a
visible
light
driven
nickel
carbonylation
catalyst.
The
combination
large
bite‐angle
Xantphos
ligand
with
nickel(0)
generates
catalyst
capable
activating
alkyl
halides
toward
at
ambient
temperature
in
presence
blue
irradiation,
and
reductive
elimination
high
energy
acid
chloride
products.
Unlike
classical
carbonylations,
where
coordination
carbon
monoxide
inhibits
reactivity
earth
abundant
catalysts,
CO‐associated
is
found
to
be
active
reaction.
Coupling
build‐up
chlorides
nucleophile
addition
can
used
access
various
amides,
esters
thioesters,
including
those
sterically
encumbered
substrates
or
metal‐reactive
functionalities.
Chinese Journal of Chemistry,
Journal Year:
2023,
Volume and Issue:
42(2), P. 177 - 189
Published: Sept. 4, 2023
Comprehensive
Summary
Carbonyl
compounds
have
attracted
considerable
attention
due
to
their
extensive
applications
in
drug
discovery.
Furthermore,
they
are
important
synthetic
intermediates
for
the
construction
of
carbon‐carbon
and
carbon‐heteroatom
bonds.
Transition‐metal‐catalyzed
carbonylation
via
insertion
CO
is
one
most
efficient
straightforward
strategies
access
carbonyl
compounds.
However,
transition‐metal‐catalyzed
carbonylative
reactions
require
expensive
toxic
noble‐metal
catalysts.
Therefore,
there
a
growing
demand
exploration
nickel‐catalyzed
earth
abundance
low
cost
nickel.
Compared
with
well‐established
palladium‐catalyzed
reactions,
analogous
transformations
been
relatively
underdeveloped.
This
primarily
because
strongly
binds
nickel,
often
resulting
catalyst
poisoning.
In
recent
years,
some
research
groups
focused
on
using
surrogates
or
NN
2
pincer
nickel
circumvent
formation
Ni(CO)
4
.
Nickel‐catalyzed
has
applied
carbonyl‐containing
compounds,
such
as
ketones,
carboxylic
acids,
thioesters,
acyl
chloride
carboxamides.
Journal of the American Chemical Society,
Journal Year:
2024,
Volume and Issue:
146(12), P. 7971 - 7978
Published: March 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
Angewandte Chemie International Edition,
Journal Year:
2022,
Volume and Issue:
62(10)
Published: Dec. 28, 2022
We
describe
here
the
development
of
a
visible
light
driven
nickel
carbonylation
catalyst.
The
combination
large
bite-angle
Xantphos
ligand
with
nickel(0)
generates
catalyst
capable
activating
alkyl
halides
toward
at
ambient
temperature
in
presence
blue
irradiation,
and
reductive
elimination
high
energy
acid
chloride
products.
Unlike
classical
carbonylations,
where
coordination
carbon
monoxide
inhibits
reactivity
earth
abundant
catalysts,
CO-associated
is
found
to
be
active
reaction.
Coupling
build-up
chlorides
nucleophile
addition
can
used
access
various
amides,
esters
thioesters,
including
those
sterically
encumbered
substrates
or
metal-reactive
functionalities.
European Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
27(12)
Published: Feb. 8, 2024
Abstract
A
novel
nickel‐catalyzed
practical
and
simple
synthesis
of
thioesters
from
amides
disulfides
has
been
developed.
Diverse
substituted
aromatic
are
capable
coupling
with
diaryl
or
dialkyl
via
C−N/S−S
bonds
cleavage
to
produce
the
desirable
in
moderate
good
yields.
This
procedure
features
cheap
metals,
easily
preparative
substrates,
providing
a
access
variety
without
toxic
thiols
CO
gas.
Green Chemistry,
Journal Year:
2024,
Volume and Issue:
26(19), P. 10265 - 10274
Published: Jan. 1, 2024
We
herein
describe
a
versatile
electron–donor–acceptor
(EDA)
mediated
thioesterification
reaction
using
aryl
sulfonium
salt
(acceptor)
with
potassium
thioacid
salts
(donor)
under
visible
light
irradiation.
Organic Letters,
Journal Year:
2025,
Volume and Issue:
unknown
Published: Jan. 24, 2025
A
straightforward
and
efficient
nickel-catalyzed
cyclization/carbonylation
transformation
of
N-allylbromoacetamides
toward
the
synthesis
2-pyrrolidinone
derivatives
has
been
developed
with
arylboronic
acids
as
reaction
partner.
This
proceeds
through
a
sequential
single-electron-transfer
pathway
via
5-exo-trig
cyclization
carbonyl
insertion
steps,
furnishing
variety
in
good
yields.
Various
useful
functional
groups
were
well
tolerated.
Moreover,
formic
acid
is
applied
CO
source
here
nickel
catalyst,
which
provides
supplement
for
carbonylation
chemistry
heterocycle
synthesis.
The Journal of Organic Chemistry,
Journal Year:
2025,
Volume and Issue:
unknown
Published: Feb. 17, 2025
This
paper
presents
a
novel
NHC-BH3-promoted
one-step
synthesis
of
disulfides
and
stibine
sulfides
using
odorless
sulfonyl
hydrazides.
The
protocol
tolerates
various
functional
groups
as
well
heterocyclic
compounds.
Mechanistic
studies
show
that
NHC-BH3
plays
two
roles:
(1)
reducing
hydrazides
into
(2)
promoting
the
cross-coupling
chlorostibine
with
disulfides.
synthesized
also
exhibit
satisfactory
anticancer
activity
against
4T1
MDA-MB-231
cancerous
cells.
European Journal of Organic Chemistry,
Journal Year:
2022,
Volume and Issue:
2022(48)
Published: Dec. 2, 2022
Abstract
Thioester
constitutes
a
fundamentally
unique
intermediate,
engaged
in
various
biosynthesis
processes
living
systems
as
well
versatile
synthon
modern
organic
synthesis.
Transition
metal
catalysis
and
radical
reaction
manifolds
have
enabled
to
enrich
the
repertoire
of
synthetic
methods
for
thioesters.
In
this
review,
we
accommodated
recent
reports
on
strategies
towards
thioester
synthesis
from
plethora
readily
available
feedstocks,
such
alkenes,
alkynes,
alcohols,
phenols
or
commodity
chemicals/synthetic
building
blocks
like
aldehydes,
halides
organoboron
reagents
under
domains.
Furthermore,
momentous
advancements
employing
progenitors
odorous
thiols
CO‐surrogates
contextually
been
emphasized,
alongside
utilization
native
free
CO
gas.
Organic & Biomolecular Chemistry,
Journal Year:
2022,
Volume and Issue:
20(45), P. 8885 - 8892
Published: Jan. 1, 2022
A
controllable
and
rapid
synthesis
of
disulfides
thiosulfonates
from
sodium
sulfinates
mediated
by
hydroiodic
acid
is
presented
for
the
first
time.
In
these
reactions,
ethanol
H2O
are
employed
as
solvents
to
generate
different
products,
can
be
further
transformed
corresponding
in
an
reaction
system.
Moreover,
simple
methods
environmentally
benign
performed
under
mild
conditions
with
a
short
time,
showing
good
functional
group
tolerance.
