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.
ACS Catalysis,
Journal Year:
2024,
Volume and Issue:
14(2), P. 1193 - 1204
Published: Jan. 9, 2024
Herein,
the
C3–H
alkylation
of
2H-indazoles
and
indoles
with
sulfoxonium
ylides
is
developed
under
visible-light
photocatalysis.
This
protocol
employs
easily
accessible
reagents,
a
wide
range
2H-indazoles,
indoles,
are
suitable
for
this
reaction
to
afford
desired
products
benign
conditions.
Synergistic
experimental
computational
studies
suggest
that
involving
photocatalysis
could
proceed
via
different
mechanistic
pathways.
For
C3-alkylation
triplet
energy
transfer
pathway
proposed
quenching
excited
photocatalyst.
Subsequently,
formed
state
undergo
radical
attack
on
C═S
moiety
ylides.
After
dissociation
DMSO
1,2-H
migration,
final
product
be
yielded.
However,
such
not
applicable
indoles.
Instead,
converted
C-centered
in
presence
KH2PO4
photoredox
The
can
C3-site
thus
lead
Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(31), P. 6736 - 6741
Published: July 29, 2024
A
visible-light-induced
photoredox
three-component
carbocyclization
reaction
of
1,7-enynes
with
sulfoxonium
ylides
and
water
is
reported.
The
protocol
provides
a
facile
entry
to
structurally
valuable
highly
functionalized
cyclopenta[c]quinoline
scaffolds
in
chemoselective
stereoselective
manner.
Salient
features
this
method
include
redox-neutral
conditions,
no
requirement
base
or
other
additive,
good
functional-group
tolerance.
Organic Chemistry Frontiers,
Journal Year:
2024,
Volume and Issue:
11(11), P. 3234 - 3241
Published: Jan. 1, 2024
Herein,
we
present
a
cascade
O–H
double
insertion
reaction
between
I
(III)
/S
(VI)
-ylides,
carboxylic
acids,
and
alcohols
under
metal-free
conditions,
enabling
the
modular
synthesis
of
unsymmetrical
α,α-
O
,
-substituted
ketones.
Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(11), P. 2249 - 2254
Published: March 7, 2024
A
copper-mediated
[3
+
2]
cyclization
of
CF3-imidoyl
sulfoxonium
ylides
and
terminal
alkynes
has
been
demonstrated.
This
work
provides
a
practical
approach
for
assembling
5-trifluoromethylpyrroles
with
the
merits
broad
substrate
scope,
good
functional
tolerance,
mild
reaction
conditions.
Control
experiments
DFT
studies
indicate
that
this
may
involve
addition
π-bonds
by
copper-carbene
radicals
hydrogen
migration.
Chemical Communications,
Journal Year:
2024,
Volume and Issue:
60(41), P. 5407 - 5410
Published: Jan. 1, 2024
A
visible-light-induced
[3+2]
cyclization
of
vinyl
azides
with
perfluoroalkyl-substituted
imidoyl
sulfoxonium
ylides
has
been
developed
and
provides
a
new
efficient
method
for
the
construction
1-pyrrolines.
Current Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
28(13), P. 978 - 990
Published: May 6, 2024
Abstract:
Photochemical
reactions
offer
unparalleled
opportunities
to
access
elusive
chemical
pathways
and
develop
innovative
strategies
for
constructing
complex
molecules.
Within
organic
synthesis,
photochemical
have
become
indispensable
tools
accessing
molecular
structures,
such
as
pharmaceuticals
natural
products.
The
ability
of
sulfur
ylides
participate
in
these
diverse
processes
has
made
them
the
synthetic
chemist's
toolbox.
use
transformations
garnered
significant
attention
chemistry
community,
they
serve
powerful
intermediates
several
transformations.
This
review
article
presents
a
comprehensive
overview
mediated
by
ylides.
Herein,
we
describe
key
aspects
reactivity
presence
light.
compounds
can
be
classified
into
three
categories:
energy
acceptors,
electron
donors,
trapping
reagents.
Organic Letters,
Journal Year:
2025,
Volume and Issue:
unknown
Published: April 24, 2025
Herein,
we
report
a
novel
ligand-switchable
Pd-catalyzed
carbene
coupling
reaction
employing
vinylethylene
carbonates
and
sulfoxonium
ylides.
By
proper
choice
of
ligands,
the
chemoselectivity
process
could
be
efficiently
regulated,
allowing
for
availability
dihydrofuran
or
dienol
scaffolds.
This
method
features
mild
conditions,
broad
scope,
remarkable
synthetic
utility.
Compound
6f
can
effectively
stimulate
secretion
GLP-1,
providing
promising
insight
into
development
small-molecule
agonists
GLP-1
receptor.
The Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
89(10), P. 6974 - 6986
Published: May 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.
