The Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
89(8), P. 5239 - 5249
Published: April 8, 2024
We
herein
disclose
a
Pd-catalyzed
Suzuki–Miyaura
coupling
of
cyclic
Morita–Baylis–Hillman
adducts
with
organoboronic
acids
under
mild
conditions,
which
allows
for
rapid
access
to
diverse
α-alkyl
substituted
cycloenones.
The
advantage
this
method
resides
in
the
employment
functionalized
allyl
alcohols
as
unprecedented
electrophilic
partners
absence
external
activators.
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:
61(33)
Published: June 13, 2022
Abstract
Multi‐component
carbonylation
of
olefins,
a
reaction
that
installs
both
carbon–carbon(heteroatom)
bond
and
carbonyl
group
across
the
double
bond,
is
an
attractive
strategy
for
alkene
functionalization.
Herein,
we
developed
novel
nickel‐catalyzed
four‐component
olefins
with
ethers
under
low
CO
gas
pressure.
Using
alcohols
amines
as
partner,
diverse
γ
‐oxy‐substituted
esters
amides
were
produced
in
good
yields
excellent
functional
tolerance.
Notably,
Naftidrofuryl,
medicine
treatment
cerebrovascular
disease
(CVD),
can
be
synthesized
by
this
process
straightforwardly.
Organic Process Research & Development,
Journal Year:
2023,
Volume and Issue:
27(3), P. 423 - 447
Published: Feb. 17, 2023
Nonprecious-metal-catalyzed
alternatives
to
powerful
precious
metal
transformations
are
of
increasing
interest
in
academia
and
the
pharmaceutical
industry
due
lower
cost,
better
sustainability,
toxicity.
With
continual
growth
broad
field
nonprecious
catalysis
(NPMC),
we
have
chosen
highlight
selected
articles
published
from
March
June
2022
which
intended
examples
NPMC
that
feel
may
be
especially
relevant
development.
We
aim
inspire
academic
industrial
innovation
through
discussion
herein.
Organic Letters,
Journal Year:
2022,
Volume and Issue:
24(22), P. 4009 - 4013
Published: May 25, 2022
A
straightforward
and
efficient
synthesis
of
α,β-unsaturated
thioesters
has
been
developed
via
a
nickel-catalyzed
thiocarbonylation
reaction
vinyl
triflates
with
arylsulfonyl
chlorides.
With
Mo(CO)6
as
both
CO
source
reductant,
variety
were
obtained
in
moderate
to
good
yields
very
functional
group
compatibility.
It
is
noteworthy
that
the
present
method
first
example
on
carbonylative
by
using
chlorides
coupling
partner.
Nature Communications,
Journal Year:
2023,
Volume and Issue:
14(1)
Published: Oct. 31, 2023
Transition
metal-catalyzed
carbonylative
reaction
with
CO
gas
are
among
the
central
task
in
organic
synthesis,
enabling
construction
of
highly
valuable
carbonyl
compound.
Here,
we
show
an
earth-abundant
nickel-catalyzed
three-component
tandem
acylzincation/cyclization
sequence
allene
and
alkylzinc
reagent
1
atm
under
mild
conditions.
This
protocol
is
featured
by
broad
functional
group
tolerance
high
selectivity,
providing
a
rapid
convenient
synthetic
method
for
diverse
fully
substituted
benzotropone
derivatives.
Mechanistic
studies
reveal
that
installation
cyano
tethered
to
moiety
enables
regio-
stereoselectivity
this
acylzincation
allene,
allowing
selective
formation
three
consecutive
C-C
bonds
efficient
manner.
ChemistrySelect,
Journal Year:
2023,
Volume and Issue:
8(32)
Published: Aug. 23, 2023
Abstract
Cyclopropanols,
due
to
their
particular
chemistry,
can
participate
in
various
synthetic
reactions
with
retention
or
cleavage
of
the
strained
three‐membered
ring.
Direct
cross‐coupling
ring‐opening
reaction
such
molecules
access
organic
compounds,
as
ketones
has
great
importance
medicinal
chemistry
and
material
sciences.
Hence,
coupling
reaction/cyclization
cyclopropanols
for
constructing
new
valuable
presence
a
transition
metal
catalyst
under
metal‐free
conditions
is
described
this
context.
The
features
are
discussed,
mechanisms
challenging
highlighted.
ACS Catalysis,
Journal Year:
2023,
Volume and Issue:
13(7), P. 4362 - 4368
Published: March 15, 2023
The
transition-metal-catalyzed
intramolecular
hydroarylation
of
alkenes
has
been
recognized
as
a
straightforward
approach
for
the
construction
3,3-disubstituted
2,3-dihydrobenzofurans.
reactions
mainly
rely
on
reductive
Heck
reaction
aryl
halides
or
direct
C–H
bond
activation
arenes
bearing
directing
group.
This
work
realizes
Rh-catalyzed
olefin-tethered
benzocyclobutenols
via
C–C
activation,
which
offers
an
alternative
to
2,3-dihydrobenzofurans
4-β-keto
moiety.
methodology
features
100%
atom
economy
and
pH-
redox-neutral
conditions,
is
applicable
late-stage
functionalization
complex
molecules.
asymmetric
variant
also
achieved
with
excellent
enantioselectivities.
