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.
European Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
26(25)
Published: April 25, 2023
Abstract
Compounds
containing
sulfonyl‐derived
functional
groups
have
received
intensive
attention
owing
to
their
widespread
applications
in
life
science,
pharmaceuticals
and
materials
science.
To
access
this
type
of
compounds,
the
multi‐component
sulfonylation
reactions
relying
on
sulfur
dioxide
(SO
2
)
insertion
strategy
emerged
as
novel
attractive
approaches
past
decade.
The
utilization
SO
surrogates
for
multicomponent
(MCRs)
improved
reaction
flexibility
step
economy.
Moreover,
some
advances
been
achieved
challenging
but
practical
asymmetric
MCRs
construction
high
value‐added
chiral
sulfones.
This
review
aims
summarize
progress
made
involving
from
2019
2022,
point
out
potentials
challenges
field.
Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(15), P. 3321 - 3325
Published: April 10, 2024
Asymmetric
sulfonylation
from
a
reaction
of
cyclopropan-1-ol,
sulfur
dioxide,
and
1-(alkynyl)naphthalen-2-ol
in
the
presence
catalytic
amount
organocatalyst
at
room
temperature
is
developed.
Axially
chiral
(S)-(E)-1-(1-(alkylsulfonyl)-2-arylvinyl)naphthalen-2-ols
are
generated
moderate
to
good
yields
with
excellent
enantioselectivity
regioselectivity
under
mild
conditions.
During
this
transformation,
γ-keto
sulfinate
situ
cyclopropan-1-ol
dioxide
acts
as
key
intermediate.
The Journal of Organic Chemistry,
Journal Year:
2025,
Volume and Issue:
unknown
Published: April 2, 2025
A
photoredox-catalyzed
radical
cascade
cyclization
of
N-(o-cyanobiaryl)acrylamides
with
sulfonyl
chlorides
for
the
construction
sulfonyl-containing
pyrido[4,3,2-gh]phenanthridines
has
been
disclosed.
The
developed
synthetic
tool
tolerates
a
broad
range
to
undergo
sequence,
including
addition,
nitrile
insertion,
and
cyclization.
Organic Letters,
Journal Year:
2023,
Volume and Issue:
25(31), P. 5916 - 5921
Published: July 27, 2023
A
copper-catalyzed
trifluoromethylthio-arylsulfonylation
between
1,3-enynes,
AgSCF3,
aryldiazonium
tetrafluoroborates,
and
SO2
(from
SOgen)
is
presented,
which
could
introduce
sulfone,
SCF3,
allene
moieties
into
one
molecule
simultaneously.
This
strategy
features
mild
reaction
conditions,
good
substrate
compatibility,
excellent
regioselectivity.
The
products
obtained
have
the
potential
for
further
conversion
other
valuable
compounds.
Initial
investigations
mechanism
suggest
that
it
may
proceed
via
a
radical
pathway.
Notably,
SOgen
was
proven
as
uniquely
effective
surrogate
in
this
transformation.
ACS Catalysis,
Journal Year:
2024,
Volume and Issue:
14(9), P. 6513 - 6524
Published: April 13, 2024
Efficient
synthesis
of
sulfonamides
has
long
been
pursued
by
chemists
due
to
their
frequent
occurrence
in
pharmaceuticals,
especially
anti-inflammatory
medicines.
The
traditional
assembly
from
sulfonyl
chlorides
and
amines,
as
well
the
recently
developed
one-step
involving
sulfur
dioxide,
still
faces
challenges
such
poor
substrate
compatibility
and/or
stringent
reaction
conditions.
Herein,
we
present
a
strategy
for
situ
generation
sulfamoyl
radicals
modular
both
alkenyl
alkyl
with
wide
applicability
(>100
examples),
mild
conditions,
easily
accessible
starting
materials.
This
method
is
successfully
applied
late-stage
modification
drug
molecules
(23
molecule
naratriptan,
15N-labeling
sulfonamides.
Organic Letters,
Journal Year:
2023,
Volume and Issue:
25(44), P. 8043 - 8047
Published: Oct. 30, 2023
Hydrosulfonylation
of
alkenes
with
readily
available
aromatic
iodides
via
a
SO2-insetion
strategy
is
presented.
The
combination
non-noble
Ni
catalysis
(iPr)3SiH
as
the
final
reductant
enables
efficient
formation
aryl
and
heteroaryl
sulfinate
intermediates,
which
undergo
Michael-type
additions
to
electron-deficient
for
initiating
hydrosulfonylation
process.
Moreover,
superiority
this
protocol
demonstrated
by
broad
substrate
scope
good
functional
group
compatibility.
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.
The Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
89(8), P. 5409 - 5422
Published: April 2, 2024
An
oxidant-assisted
tandem
sulfonylation/cyclization
of
electron-deficient
alkenes
with
4-alkyl-substituted
Hantzsch
esters
and
Na2S2O5
for
the
preparation
3-alkylsulfonylated
oxindoles
under
mild
conditions
in
absence
a
photocatalyst
transition
metal
catalyst
is
established.
The
mechanism
studies
show
that
alkyl
radicals,
which
come
from
cleavage
C–C
bond
4-substituted
oxidant
conditions,
subsequently
undergo
situ
insertion
sulfur
dioxide
to
generate
crucial
alkylsulfonyl
radical
intermediates.
This
three-component
reaction
provides
an
efficient
facile
route
construction
alkylsulfonylated
avoids
use
highly
toxic
chlorides
or
hydrazines
as
sources.
The Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
89(13), P. 9672 - 9680
Published: June 13, 2024
A
three-component
reaction
of
1-(1H-indol-1-yl)isoquinolines
or
1-(pyridin-2-yl)-1H-indoles,
DABCO·(SO2)2,
and
thianthrenium
salts
under
synergistic
photoredox
palladium
catalysis
is
accomplished.
This
direct
C–H
bond
sulfonylation
indoles
with
the
insertion
sulfur
dioxide
mild
conditions
works
efficiently,
giving
rise
to
a
wide
range
2-sulfonated
in
moderate
good
yields
conditions.
In
this
protocol,
generality
aryl/alkyl
demonstrated
as
well.
radical
process
combined
proposed.
