Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(44), P. 9592 - 9597
Published: Oct. 29, 2024
We
report
here
the
use
of
pyridin-2-yl
benzenesulfonates
as
sulfonylation
reagents
in
a
difunctionalization
reaction
based
on
oxy-pyridinium
ylide
chemistry,
providing
an
effective
protocol
for
installation
both
sulfonyl
group
and
pyridone
moiety
into
one
molecule.
Density
functional
theory
(DFT)
calculations
disclose
that
process
might
proceed
through
sequential
metal-bound
formation,
keto-enol
tautomerism,
migratory
rearrangement
group.
Angewandte Chemie International Edition,
Journal Year:
2024,
Volume and Issue:
63(32)
Published: May 13, 2024
Abstract
We
report
an
iron‐catalyzed
decarboxylative
C(sp
3
)−O
bond‐forming
reaction
under
mild,
base‐free
conditions
with
visible
light
irradiation.
The
transformation
uses
readily
available
and
structurally
diverse
carboxylic
acids,
iron
photocatalyst,
2,2,6,6‐tetramethylpiperidine
1‐oxyl
(TEMPO)
derivatives
as
oxygenation
reagents.
process
exhibits
a
broad
scope
in
acids
possessing
wide
range
of
stereoelectronic
properties
functional
groups.
developed
was
applied
to
late‐stage
series
bio‐active
molecules.
leverages
the
ability
complexes
generate
carbon‐centered
radicals
directly
from
by
photoinduced
carboxylate‐to‐iron
charge
transfer.
Kinetic,
electrochemical,
EPR,
UV/Vis,
HRMS,
DFT
studies
revealed
that
TEMPO
has
triple
role
reaction:
reagent,
oxidant
turn
over
Fe‐catalyst,
internal
base
for
acid
deprotonation.
obtained
adducts
represent
versatile
synthetic
intermediates
were
further
engaged
C−C
C‐heteroatom
reactions
using
commercial
organo‐photocatalysts
nucleophilic
Bulletin of the Korean Chemical Society,
Journal Year:
2024,
Volume and Issue:
45(9), P. 738 - 758
Published: Sept. 1, 2024
Abstract
Halogenation
is
one
of
the
most
important
transformations
in
organic
synthesis.
Halogenated
compounds
are
employed
many
reactions
to
prepare
useful
molecules.
Many
methods
have
been
developed
introduce
halogens
into
different
compounds.
Visible
light‐mediated
efficient,
low‐toxic,
and
mild‐condition
applied
for
various
chemistry
transformations.
Remarkably,
there
has
an
increasing
development
application
visible
light‐induced
halogenation
recent
years.
Herein,
we
present
a
comprehensive
summary
including
chlorination,
bromination,
iodination
under
light
irradiation
since
2020.
The Journal of Organic Chemistry,
Journal Year:
2025,
Volume and Issue:
unknown
Published: May 15, 2025
A
sustainable,
photocatalytic
approach
for
the
synthesis
of
oxindoles
and
chroman-4-ones
was
developed
using
carboxylate
salts
as
radical
precursors
FeCl3
a
catalyst.
The
reaction
proceeds
via
decarboxylative
cyclization
mechanism
triggered
by
ligand-to-metal
charge
transfer
under
visible
light
irradiation,
operating
efficiently
at
room
temperature.
This
method
demonstrates
excellent
substrate
scope,
including
use
various
alkyl
carboxylates,
functional
group
tolerance
offers
scalable
pathway
gram-scale
synthesis,
highlighting
its
practical
application.
Angewandte Chemie,
Journal Year:
2024,
Volume and Issue:
136(32)
Published: May 13, 2024
Abstract
We
report
an
iron‐catalyzed
decarboxylative
C(sp
3
)−O
bond‐forming
reaction
under
mild,
base‐free
conditions
with
visible
light
irradiation.
The
transformation
uses
readily
available
and
structurally
diverse
carboxylic
acids,
iron
photocatalyst,
2,2,6,6‐tetramethylpiperidine
1‐oxyl
(TEMPO)
derivatives
as
oxygenation
reagents.
process
exhibits
a
broad
scope
in
acids
possessing
wide
range
of
stereoelectronic
properties
functional
groups.
developed
was
applied
to
late‐stage
series
bio‐active
molecules.
leverages
the
ability
complexes
generate
carbon‐centered
radicals
directly
from
by
photoinduced
carboxylate‐to‐iron
charge
transfer.
Kinetic,
electrochemical,
EPR,
UV/Vis,
HRMS,
DFT
studies
revealed
that
TEMPO
has
triple
role
reaction:
reagent,
oxidant
turn
over
Fe‐catalyst,
internal
base
for
acid
deprotonation.
obtained
adducts
represent
versatile
synthetic
intermediates
were
further
engaged
C−C
C‐heteroatom
reactions
using
commercial
organo‐photocatalysts
nucleophilic
Chinese Journal of Chemistry,
Journal Year:
2024,
Volume and Issue:
unknown
Published: Dec. 2, 2024
Comprehensive
Summary
Herein,
we
report
a
rare
example
of
three‐component
net‐oxidative
sulfonylation
SO
2
surrogate
with
an
oxidatively
activated
radical
precursor
under
mild
and
metal‐
external‐oxidant‐free
conditions.
The
mildness
sustainability
the
reaction
are
enabled
by
photoelectrocatalysis,
3‐aza‐1,5‐dienes,
organotrifluoroborates
1,4‐diazabicyclo[2.2.2]octane
bis(sulfur
dioxide)
adduct
(DABSO)
undergo
sulfonylative
cyclization
to
afford
sulfono
4‐pyrrolin‐2‐ones
in
atom‐economical
manner
broad
substrate
scope
good
functional‐group
tolerance.
protocol
is
amenable
late‐stage
diversification
complex
molecular
architectures
as
well
gram‐scale
synthesis.
Sunlight
could
be
used
light
source,
conducted
all‐solar
mode
using
commercially
available
photovoltaic
panel
generate
electricity
situ
.
Mechanistic
studies
reveal
that
generated
(DABCO),
which
was
generally
innocent
previous
reactions,
functions
electron
shuttle
between
photocatalytic
cycle
reactants.
