Nickel-Catalyzed Modular Four-Component 1,4-Alkylcarbonylation of 1,3-Enynes to Tetra-Substituted CF3–Allenyl Ketones
ACS Catalysis,
Год журнала:
2024,
Номер
14(4), С. 2144 - 2150
Опубликована: Янв. 25, 2024
The
modular
four-component
carbonylation
of
unsaturated
hydrocarbons
represents
an
elegant
strategy
for
the
one-pot
synthesis
complex
carbonyl
compounds.
However,
this
is
currently
focused
on
1,2-difunctionalization
olefins
or
alkynes,
and
1,4-alkylcarbonylation
1,3-enynes
remains
unexplored.
In
study,
we
report
a
Ni-catalyzed
CF3-containing
under
1
atm
CO,
which
affords
tetra-substituted
CF3-allenyl
ketones
with
good
yields
selectivity.
This
protocol
features
mild
conditions,
broad
substrate
scope,
acceptable
functional
group
compatibility.
Control
experiments
revealed
that
reactivity
oxime
esters
(regulated
by
leaving
groups)
polarity
matching
are
crucial
success
cascade.
Preliminary
mechanistic
studies
suggest
acyl
nickel
key
intermediate
in
transformation.
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
Palladium-Catalyzed Three-Component Cascade Carbonylation Reaction to Construct Benzofuran Derivatives
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(11), С. 7741 - 7746
Опубликована: Май 14, 2024
A
novel
three-component
cyclization
carbonylation
reaction
of
iodoarene-tethered
propargyl
ethers
with
amine
and
CO
is
reported.
This
palladium-catalyzed
cascade
undergoes
a
sequence
oxidative
addition,
unsaturated
bond
migration,
carbonyl
insertion,
nucleophilic
attack
to
deliver
the
benzofuran
skeleton.
Both
aromatic
amines
aliphatic
could
proceed
smoothly
in
this
transformation
under
one
atm
CO.
Язык: Английский
Cu-catalyzed alkylarylation of alkenes via N-directed remote C(sp3)–H functionalization
Organic Chemistry Frontiers,
Год журнала:
2024,
Номер
11(5), С. 1484 - 1489
Опубликована: Янв. 1, 2024
Herein,
we
report
a
copper-catalyzed
alkylarylation
reaction
of
alkenes
using
N
-fluoroamides
and
arylboronic
acids.
Язык: Английский
Nickel-Catalyzed Narasaka–Heck Cyclization Carbonylation of Unsaturated Oxime Esters with Arylboronic Acids
Organic Letters,
Год журнала:
2024,
Номер
26(37), С. 7834 - 7840
Опубликована: Сен. 5, 2024
The
Narasaka-Heck
reaction
is
one
of
the
most
straightforward
methods
for
constructing
pyrroline
derivatives.
Herein,
we
report
a
novel
nickel-catalyzed
three-component
carbonylation
reaction,
which
cleverly
realizes
continuous
construction
C(sp
Язык: Английский
Nickel-Catalyzed Cyclization/Carbonylation Reaction of N-Allylbromoacetamides with Arylboronic Acids toward 2-Pyrrolidinones
Hucheng Ma,
Chen-Yang Hou,
Ruyi Zhao
и другие.
Organic Letters,
Год журнала:
2025,
Номер
unknown
Опубликована: Янв. 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.
Язык: Английский
Palladium-Catalyzed and Photoinduced Site-Selective Alkynylation and Oxidation of the Remote C(sp3)–H
Organic Letters,
Год журнала:
2025,
Номер
unknown
Опубликована: Март 10, 2025
A
general
and
efficient
method
for
the
direct
alkynylation
oxidation
of
remote
C(sp3)-H
bonds
under
photoirradiation
is
described.
In
this
reaction,
Pd
catalyst
acts
as
both
a
photocatalyst
to
generate
nitrogen
radical
cross-coupling
with
terminal
alkyne.
Attractive
features
system
include
good
functional
group
tolerance,
scalability,
convenient
reagents,
an
operating
system.
The
utility
protocol
highlighted
by
its
application
derivatization
several
valuable
aza-heterocycles
such
caspase-3
inhibitor
azepinone
derivatives.
Язык: Английский
Nickel/Photoredox-Catalyzed Carbonylative Cross-Electrophile Coupling of Organohalides and Carboxylic Acid Esters with Phenyl Formate
Organic Letters,
Год журнала:
2024,
Номер
26(30), С. 6518 - 6522
Опубликована: Июль 22, 2024
A
photoinduced
nickel-catalyzed
reductive
carbonylative
coupling
from
organohalides
and
Язык: Английский
Ultrasound-Assisted Remote Benzylic C(sp3)–H Alkylation of N-Fluoroamides with Enol Silanes
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(22), С. 16473 - 16484
Опубликована: Ноя. 7, 2024
We
have
developed
an
ultrasound-assisted
remote
benzylic
C(sp3)–H
alkylation
of
N-fluorobenzamides
with
enol
silanes;
a
series
β-aryl
substituted
propiophenones
was
generated
in
good
to
high
yields.
This
reaction
represents
formal
C(sp3)–C(sp3)
coupling
and
features
simplicity,
efficiency,
wide
substrate
scope
multiple-step
sequential
process,
which
involves
N–F
homolysis,
1,5-hydrogen
atom
transfer,
radical
addition,
oxidation
by
copper(II)
salt,
removal
the
trimethylsilyl
group.
Also,
DFT
theoretical
calculations
Marcus
theory
were
employed
consolidate
proposed
mechanism.
Язык: Английский