Recent Advances in the Catalytic Synthesis of α‐Ketoamides
The Chemical Record,
Год журнала:
2025,
Номер
unknown
Опубликована: Апрель 21, 2025
Abstract
α
‐Ketoamides
are
privileged
chemical
entities
featuring
a
carbonyl
group
bonded
to
an
amide.
Bearing
two
pronucleophilic
and
proelectrophilic
sites,
this
structural
scaffold
exhibits
distinct
properties
unparalleled
biological
activity.
Owing
its
wide
application
in
medicinal,
agricultural,
synthetic
chemistry,
methods
for
assembling
moiety
ever‐growing
demand.
With
the
increasing
focus
on
green
synthesis,
traditional
routes
‐ketoamides
have
faded
recent
years
giving
rise
development
of
photocatalytic,
electrosynthetic,
microwave‐assisted
catalytic
protocols.
We
hereby
provide
comprehensive
critical
summary
all
advancements
witnessed
field
from
2016
present.
Язык: Английский
Maleimide‐Controlled Formation of Indanonylpyrrolinediones and Spiroindanonylpyrrolinediones via Rh(III)‐Catalyzed C−H Activation of Sulfoxonium Ylides
Advanced Synthesis & Catalysis,
Год журнала:
2023,
Номер
365(24), С. 4595 - 4602
Опубликована: Ноя. 1, 2023
Abstract
A
substrate‐controlled
[4+1]
annulation
of
sulfoxonium
ylides
with
maleimides
via
Rh(III)‐catalyzed
C−H
bond
activation
is
developed.
The
reaction
2‐methyl‐
N
‐arylmaleimides
in
the
presence
AgNTf
2
diastereoselectively
provides
diversely
functionalized
indanonylpyrroline‐2,5‐dione
derivatives.
Furthermore,
AgBF
4
,
subsequent
leads
to
biologically
intriguing
various
spiroindanonylpyrroline‐2,5‐diones.
This
methodology
offers
a
broad
substrate
scope,
good
functional
group
tolerance,
and
diastereoselectivity.
Язык: Английский
Lithium Bromide-Promoted Formal C(sp3)–H Bond Insertion Reactions of β-Carbonyl Esters with Sulfoxonium Ylides to Synthesize 1,4-Dicarbonyl Compounds
Hailin Guo,
Yuhao Ding,
Jing-Wen Fan
и другие.
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(10), С. 6974 - 6986
Опубликована: Май 4, 2024
A
LiBr-promoted
formal
C(sp3)–H
bond
insertion
reaction
between
β-carbonyl
esters
and
sulfoxonium
ylides
is
established.
This
practical
has
a
wide
range
of
substrate
scope
for
both
to
give
variety
1,4-dicarbonyl
compounds
with
43–94%
yields.
The
features
transition-metal-free
conditions
exclusive
C-alkylation
chemselectivity.
use
bench-stable
overcomes
previous
methods
that
require
transition
metal
as
catalysts
unstable
diazo
or
toxic
haloketones
alkylation
reagents.
Язык: Английский
Visible‐Light‐Mediated Synthesis of α‐Ketoamides via Oxidative Amination of 2‐Bromoacetophenones Using Eosin Y as a Photoredox Catalyst
Chemistry - An Asian Journal,
Год журнала:
2023,
Номер
18(19)
Опубликована: Авг. 29, 2023
An
oxidative
amination
of
2-bromoacetophenones
has
been
accomplished
to
provide
α-ketoamides
by
using
photoredox
catalysis
with
air
as
oxidant.
The
reactants
are
readily
accessible,
and
the
method
is
endowed
broad
substrate
scope
good
functional
group
tolerance.
practicality
approach
also
shown
a
gram-scale
reaction.
Язык: Английский
Copper-Mediated Decarboxylative Coupling of 3-Indoleacetic Acids with Sulfoxonium Ylides for the Synthesis of α-Acetoxyl Ketones
Organic Letters,
Год журнала:
2024,
Номер
26(28), С. 5940 - 5945
Опубликована: Июль 11, 2024
The
most
convenient
and
direct
method
of
synthesizing
an
α-acyloxy
ketone
is
the
reaction
a
diazo
compound
with
carboxylic
acid
via
O-H
insertion.
However,
due
to
limitations
in
preparing
storing
compounds,
application
this
restricted.
In
study,
Cu(OAc)
Язык: Английский
Selective Synthesis of Amides and α-Ketoamides via Electrochemical Decarboxylation and Dehydration
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(15), С. 10498 - 10510
Опубликована: Июль 16, 2024
An
electrochemical
and
selective
decarboxylation
dehydration
using
α-keto
acids
with
amines
is
accomplished,
which
leads
to
the
easy
accessibility
of
amides
α-ketoamides,
are
not
only
ubiquitous
valuable
structure
motifs
found
in
pharmaceuticals,
but
also
versatile
building
blocks
synthetic
chemistry.
Notably,
for
this
efficient
green
protocol,
neither
metal
catalysts
nor
external
oxidants
required.
The
process
exhibits
a
broad
scope
functional
group
tolerance
deliver
various
α-ketoamides.
Moreover,
these
two
reactions
have
been
applied
late-stage
derivatization
can
be
safely
conducted
on
gram
scale.
Язык: Английский
Electrochemical Formation of α-Ketoamides from Ketoximes through Non-Beckmann Mechanism Pathway
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(9), С. 6238 - 6246
Опубликована: Апрель 23, 2024
α-Ketoamides
are
highly
valued
in
synthetic
chemistry
due
to
their
incorporation
into
diverse
natural
products
and
drug
molecules.
Here,
we
present
an
innovative
electrochemical
approach
for
constructing
α-ketoamides,
utilizing
a
mild
environmentally
friendly
strategy
user-friendly
undivided
cell
setup
under
constant
current.
The
excellent
functional-group
tolerance,
convenient
accessibility
of
reaction
instruments
starting
materials,
easy
scalability
collectively
enhance
the
importance
this
protocol
compared
previous
challenging
methods.
Additionally,
mechanistic
insight
is
obtained
through
investigation
cyclic
voltammograms
reactants.
Язык: Английский
Synthesis of N-Aryl-4-trifluoromethylthiazol-2-amines via Insertion/Annulation of Trifluoromethylimidoyl Sulfoxonium Ylides with Sodium Thiocyanate
Yuhao Ding,
Yaopeng Liu,
Jin Ge
и другие.
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(17), С. 12255 - 12262
Опубликована: Авг. 16, 2024
An
efficient
p-TsOH-mediated
insertion
of
sodium
thiocyanate
into
trifluoromethylimidoyl
sulfoxonium
ylides
has
been
reported,
affording
annulated
N-aryl-4-trifluoromethylthiazol-2-amines
in
42–84%
yields
a
one-pot
manner.
This
protocol
encompasses
variety
with
serving
as
the
source
"S–C═N"
moiety
thiazole
ring.
The
versatile
transformations
resulting
pharmacologically
important
were
also
demonstrated.
Язык: Английский
LiBr-Promoted Reaction of β-Ketodithioesters and Thioamides with Sulfoxonium Ylides to Synthesize Functionalized Thiophenes
Organic Letters,
Год журнала:
2024,
Номер
26(43), С. 9401 - 9406
Опубликована: Окт. 22, 2024
An
operationally
simple
and
highly
efficient
synthesis
of
functionalized
thiophenes
has
been
developed
by
LiBr
promoted
heteroannulation
β-ketodithioesters
thioamides
with
bench-stable
sulfoxonium
ylides
in
open
air
for
the
first
time.
This
one-pot
strategy
involves
formal
Csp3–H
bond
insertion/intramolecular
cyclization
cascade,
featuring
readily
accessible
starting
materials,
TM
additive-free
condition,
broad
substrate
scope,
high
functional
group
compatibility,
scalability.
Moreover,
carbonyl,
thiomethyl,
amino
groups
resulting
thiophene
provide
a
good
handle
on
downstream
transformations.
Язык: Английский
Construction of α‐ketoamides via Photoredox‐Catalyzed N−H Insertion of Amines by Sulfoxonium Ylides
Advanced Synthesis & Catalysis,
Год журнала:
2024,
Номер
unknown
Опубликована: Ноя. 8, 2024
Abstract
Herein,
we
report
the
development
of
photoredox‐catalyzed
N−H
insertion
sulfoxonium
ylides
with
amines
via
oxidative
single‐electron
transfer
(SET).
These
reactions
exhibit
broad
substrate
scope
(32
examples)
and
offer
operationally
simple,
scalable
procedures
for
accessing
α
‐ketoamides
in
a
single
step.
Mechanistic
studies
control
experiments
confirm
participation
photogenerated
carbon
radical
facilitating
(SET)
from
to
initiate
reaction.
Язык: Английский