Scientia Sinica Chimica,
Journal Year:
2022,
Volume and Issue:
53(2), P. 129 - 144
Published: Oct. 20, 2022
Amides
compounds
have
a
wide
range
of
application,
and
many
transforming
strategies
been
reported.
Transition
metals-catalyzed
non-decarbonylative
cross-coupling
reaction
amides
has
gained
considerable
attention
due
to
low
cost,
high
efficiency,
good
compatibility
functional
groups.
The
reactions
following
disadvantages
the
inherent
nature
catalytic
system:
expensive
catalysts,
complex
ligands,
cocatalysts
trace
metals
residues.
transition-metal-free
amide
activation
for
synthesis
ketones
avoid
above
problems
with
efficiency
simple
treatment.
From
perspective
sustainable
development,
development
strategy
without
transition
great
significance.
In
this
paper,
by
C–N
bond
cleavage
were
reviewed.
main
contents
as
follows:
(1)
direct
addition
alkali
metal/alkaline-earth
metal
reagents
amides;
(2)
Brønsted
base-promoted
alkanes
activated
groups;
(3)
based
on
strategy;
(4)
acid-promoted
Friedel-Crafts
acylation
amide;
(5)
Lewis
between
alkyl
ketone.
This
review
provides
inspiration
subsequent
economic
green
reaction.
Chemical Science,
Journal Year:
2021,
Volume and Issue:
13(5), P. 1192 - 1209
Published: Dec. 8, 2021
Sulfoxonium
ylides
are
important
surrogates
for
diazo
compounds,
and
their
use
in
industry
as
safer
alternatives
has
been
evaluated
during
recent
years.
Beyond
the
known
classical
transformations,
these
have
also
used
a
surprising
plethora
of
novel
intrinsic
chemical
reactions,
especially
Bench
stability
handling
an
advantage
this
class
organosulfur
molecules.
Despite
this,
efficient
asymmetric
specifically
catalytic
enantioselective
versions,
only
recently
reported,
there
specific
reasons
this.
This
perspective
article
covers
topic
from
first
studies
up
to
latest
advances,
giving
personal
perspectives
showing
main
challenges
area
coming
The Journal of Organic Chemistry,
Journal Year:
2022,
Volume and Issue:
88(19), P. 13371 - 13391
Published: Sept. 2, 2022
Ground-state
destabilization
of
the
N–C(O)
linkage
represents
a
powerful
tool
to
functionalize
historically
inert
amide
bond.
This
burgeoning
reaction
manifold
relies
on
availability
bond
precursors
that
participate
in
weakening
nN
→
π*C=O
conjugation
through
N–C
twisting,
N
pyramidalization,
and
electronic
delocalization.
Since
2015,
acyl
activation
ground-state
has
been
achieved
by
transition-metal-catalyzed
oxidative
addition
bond,
generation
radicals,
transition-metal-free
addition.
Perspective
summarizes
contributions
our
laboratory
development
new
ground-state-destabilized
enabled
twist
synthetic
utility
amides
cross-coupling
reactions
reactions.
The
use
as
electrophiles
enables
plethora
previously
unknown
transformations
such
coupling,
decarbonylative
radical
coupling
forge
C–C,
C–N,
C–O,
C–S,
C–P,
C–B
bonds.
Structural
studies
activated
catalytic
systems
developed
past
decade
enable
view
change
from
"traditionally
inert"
"readily
modifiable"
functional
group
with
continuum
reactivity
dictated
destabilization.
Organic Letters,
Journal Year:
2023,
Volume and Issue:
25(7), P. 1214 - 1217
Published: Feb. 9, 2023
An
efficient
catalyst-
and
additive-free
facile
synthesis
of
α-carbonyl-α′-amide
sulfoxonium
ylides
from
isocyanates
β-ketosulfoxonium
with
complete
atom
economy
has
been
described.
The
adorned
various
functional
groups
were
well-tolerated
afforded
moderate
to
high
yields
the
ylide
derivatives.
Finally,
using
large-scale
reactions
converting
synthesized
into
other
valuable
compounds,
we
demonstrated
practicality
this
synthetic
method.
Organic Letters,
Journal Year:
2022,
Volume and Issue:
24(43), P. 7924 - 7927
Published: Oct. 20, 2022
A
library
of
thiazoles
and
selenothiazoles
were
synthesized
via
Ir-catalyzed
ylide
insertion
chemistry.
This
process
is
a
functional
group,
particularly
heterocycle-substituent
tolerant.
was
applied
to
the
synthesis
fanetizole,
an
anti-inflammatory
drug,
thiazole-containing
drug
fragment
that
binds
peptidyl-tRNA
hydrolase
(Pth)
in
Neisseria
gonorrheae
bacteria.
Organic Letters,
Journal Year:
2023,
Volume and Issue:
25(19), P. 3352 - 3357
Published: May 4, 2023
Rh-catalyzed
weak
and
traceless
directing-group-assisted
cascade
C–H
activation
annulation
of
sulfoxonium
ylides
with
vinyl
cyclopropanes
as
a
coupling
partner
have
been
accomplished
to
furnish
functionalized
cyclopropane-fused
tetralones
at
moderate
temperature.
The
C–C
bond
formation,
cyclopropanation,
functional
group
tolerance,
late-stage
diversifications
drug
molecules,
scale-up
are
the
important
practical
features.
The Journal of Organic Chemistry,
Journal Year:
2025,
Volume and Issue:
unknown
Published: Feb. 2, 2025
A
mild
and
efficient
protocol
for
the
perhaloacylation
of
α-carbonyl
sulfoxonium
ylides
has
been
developed.
The
commercially
available
perfluoro-
perchloroacid
anhydrides
were
used
as
acylating
agents
in
catalyst-
additive-free
reactions
to
access
α-carbonyl-α'-perhaloacyl
high
yields.
reaction
offers
a
simple
method
prepare
valuable
polyfluorinated
organosulfur
molecules.
Molecules,
Journal Year:
2025,
Volume and Issue:
30(3), P. 655 - 655
Published: Feb. 1, 2025
This
review
probes
the
recent
developments
in
stereoselective
reactions
within
area
of
sulfoxonium
ylide
chemistry
since
early
2000s.
An
abundance
research
has
been
applied
to
its
emergence
1960s.
There
a
continued
effort
then
with
work
traditional
areas,
such
as
epoxidation,
aziridination
and
cyclopropanation.
Efforts
have
also
novel
olefination
insertion
reactions,
develop
methodologies
using
organocatalysis
transition
metal
catalysis.
The
growing
interrupted
Johnson–Corey–Chaykovsky
is
described,
whereby
unexpected
cyclopropanation
epoxidation
developed.
In
general,
most
observed
mechanistic
pathway
ylides
formal
cycloaddition:
(2
+
1)
(e.g.,
epoxides,
cyclopropanes,
aziridines),
(3
oxetanes,
azetidines),
(4
indanones,
indolines).
involves
formation
zwitterionic
intermediate
through
nucleophilic
addition
carbanion
an
electrophilic
site.
intramolecular
cyclization
occurs,
constructing
cyclic
product.
Insertion
X–H
bonds
X
=
S,
N
or
P)
are
observed,
protonation
followed
by
X,
form
inserted
Advanced Science,
Journal Year:
2025,
Volume and Issue:
unknown
Published: April 2, 2025
Amide
and
alkene
moieties
are
frequently
found
in
natural
products
privileged
structures
pharmaceuticals
agrochemicals.
Moreover,
vinyl
sulfoxonium
ylide
can
be
converted
into
a
broad
range
of
high-value
compounds,
thus
they
have
been
widely
employed
organic
synthesis.
However,
the
synthesis
alkene-substituted
amide-sulfoxonium
ylides
via
intermolecular
hydrocarbonation
alkynes
remains
underexplored.
This
study
describes
development
high-throughput
approach
to
provide
diverse
functionalized
E-alkene
substituted
(hetero)amide-sulfoxonium
ylides.
The
reaction
occurs
under
mild
metal-free
conditions,
employing
as
highly
effective
nucleophiles,
which
participate
Michael
addition
reactions
with
various
alkynes,
such
esters,
thioesters,
ketones,
amides,
sulfones.
low-cost,
operationally
simple
has
substrate
scope,
high
functional
group
compatibility,
excellent
regio-
stereoselectivity,
making
it
suitable
for
transformation
structurally
complex
molecules.
Furthermore,
obtained
stabilized
directly
useful
valuable
1,5-dicarbonyl
thiabenzene
1-oxide
compounds.
