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.
Organic Chemistry Frontiers,
Journal Year:
2024,
Volume and Issue:
11(6), P. 1678 - 1684
Published: Jan. 1, 2024
This
method
allows
for
the
enantioselective
synthesis
of
β-azide
sulfones
via
iron-catalyzed
vicinal
azide-sulfonylation
acrylamides.
It
makes
first
instance
achieving
asymmetric
construction
through
iron
catalysis
with
SO
2
insertion.
Advanced Synthesis & Catalysis,
Journal Year:
2023,
Volume and Issue:
365(12), P. 1989 - 1994
Published: May 31, 2023
Abstract
An
oxidative
sulfonylation/cyclisation
of
N
‐propargylindoles
with
Hantzsch
esters
through
sulfur
dioxide
insertion
has
been
developed.
The
method
uses
Na
2
S
O
5
as
source
along
4‐alkyl‐substituted
radical
precursors
for
accessing
sulfonyl
radicals,
and
allows
the
synthesis
2‐sulfonated
9
H
‐pyrrolo[1,2‐
a
]indoles.
Helvetica Chimica Acta,
Journal Year:
2024,
Volume and Issue:
107(2)
Published: Feb. 1, 2024
Abstract
Functionalized
cubanes
are
attractive
scaffolds
for
medicinal
chemists
as
they
bioisosteres
of
benzene
rings.
The
replacement
a
ring
by
cubane,
in
bioactive
compound,
can
have
beneficial
effect
on
the
biological
activity
such
compound.
Thus,
design
new
molecular
cubyl
building
blocks
is
importance.
In
this
review,
we
will
focus
functionalization
creating
C−C,
C−heteroatom
bonds
e.
g.
C−N,
C−O,
C−B,
C−P
and
C−S
bonds.
Different
methods
reported
involving
organometallics,
radicals,
ionic
species.
Mechanisms
included
when
relevant.
Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(20), P. 4251 - 4256
Published: May 14, 2024
β-amino
sulfones
are
important
motifs
found
in
natural
products
and
active
pharmaceutical
compounds.
Herein,
we
report
a
general
highly
regioselective
intermolecular
aminosulfonylation
of
alkenes
via
the
homolysis
sulfinyl
oximes
from
ketoximes
chloride.
This
method
features
catalyst-free,
step-efficient
functionalization
prominent
functional
group
tolerance,
providing
straightforward,
green,
widely
applicable
approach
to
accessing
sulfone
derivatives.
Organic Letters,
Journal Year:
2024,
Volume and Issue:
unknown
Published: Sept. 30, 2024
The
development
of
efficient
methods
for
synthesizing
β-silyl
amines
has
long
been
a
significant
goal
in
organic
synthesis.
Previous
mainly
relied
on
the
use
prefunctionalized
substrates
or
special
reagents.
Herein,
we
present
visible-light-promoted
synthesis
approach
amines,
utilizing
combination
photoinduced
energy
and
hydrogen
atom
transfer
processes.
Using
flow
chemistry
technology,
variety
valuable
skeletons,
including
α-amino
esters,
can
be
produced
from
readily
available
feedstocks
such
as
hydrosilanes
simple
alkanes.
Moreover,
strategy's
full-process
fluidized
production
capability
highlights
its
potential
industrial-scale
manufacturing.
Mechanistic
studies
revealed
that
oxime
esters
act
radical
precursors
well
Chemical Communications,
Journal Year:
2024,
Volume and Issue:
unknown
Published: Jan. 1, 2024
The
synthesis
of
β-amino
acid
esters
was
achieved
through
the
combination
three-components
radical
coupling,
hydrogen
atom
transfer
and
energy
processes,
utilizing
alkyl
formates
olefins
as
raw
materials
in
a
light-induced
reaction.
The Journal of Organic Chemistry,
Journal Year:
2025,
Volume and Issue:
unknown
Published: March 16, 2025
A
photocatalytic
radical
sulfonarylation
of
N-arylacrylamides
via
a
three-component
cascade
cyclopropyl
alcohol
ring
opening/sulfur
dioxide
insertion/sulfonyl
addition/cyclization
sequence
has
been
developed.
This
method
employs
alcohols
as
the
precursors
β-carbonyl
alkyl
radicals
and
Na2S2O5
cheap
source
sulfur
dioxide.
By
using
this
procedure,
wide
variety
γ-keto-sulfone-substituted
oxindoles
were
facilely
synthesized.
Nature Communications,
Journal Year:
2025,
Volume and Issue:
16(1)
Published: April 16, 2025
Abstract
Aromatic
compounds
serve
as
key
feedstocks
in
the
chemical
industry,
typically
undergoing
functionalization
or
full
reduction.
However,
partial
reduction
via
dearomative
sequences
remains
underexplored
despite
its
potential
to
rapidly
generate
complex
three-dimensional
scaffolds
and
existing
strategies
often
require
metal-mediated
multistep
processes
suffer
from
limited
applicability.
Herein,
a
photocatalytic
radical
cascade
approach
enabling
difunctionalization
through
selective
spirocyclization/imination
of
nonactivated
arenes
is
reported.
The
method
employs
bifunctional
oxime
esters
carbonates
introduce
multiple
functional
groups
single
step,
forming
spirocyclic
motifs
iminyl
functionalities
N–O
bond
cleavage,
hydrogen-atom
transfer,
addition,
spirocyclization,
radical-radical
cross-coupling.
reaction
constructs
up
four
bonds
(C−O,
C−C,
C−N)
simple
starting
materials.
Its
broad
applicability
demonstrated
on
various
substrates,
including
pharmaceuticals,
it
compatible
with
scale-up
under
flow
conditions,
offering
streamlined
synthesizing
highly
decorated
frameworks.
