Advanced Synthesis & Catalysis,
Journal Year:
2023,
Volume and Issue:
365(4), P. 555 - 567
Published: Jan. 18, 2023
Abstract
A
direct,
visible‐light‐mediated,
radical‐cascade
addition/sulfonylation/cyclization
reaction
with
DABCO
⋅
(SO
2
)
and
thianthrenium
salts
is
reported
herein.
This
protocol
provides
operationally‐convenient
access
to
various
sulfonated
functionalized
indole
[2,1‐a]
isoquinolines
under
mild
conditions.
transformation
features
high
functional‐group
tolerance,
operational
ease,
broad
substrate
scope.
Preliminary
studies
reveal
that
the
method
undergoes
a
radical
pathway.
magnified
image
Chemical Communications,
Journal Year:
2023,
Volume and Issue:
59(26), P. 3821 - 3826
Published: Jan. 1, 2023
In
this
highlight,
we
survey
recent
exciting
advances
in
asymmetric
sulfonylation
by
using
sulfur
dioxide
surrogates,
and
discuss
induction
modes,
reaction
mechanisms,
substrate
scope
opportunities
for
further
studies.
Nature Communications,
Journal Year:
2024,
Volume and Issue:
15(1)
Published: June 19, 2024
Abstract
Sulfur-containing
scaffolds
originating
from
small
alkyl
fragments
play
a
crucial
role
in
various
pharmaceuticals,
agrochemicals,
and
materials.
Nonetheless,
their
synthesis
using
conventional
methods
presents
significant
challenges.
In
this
study,
we
introduce
practical
efficient
approach
that
harnesses
hydrogen
atom
transfer
photocatalysis
to
activate
volatile
alkanes,
such
as
isobutane,
butane,
propane,
ethane,
methane.
Subsequently,
these
nucleophilic
radicals
react
with
SO
2
yield
the
corresponding
sulfinates.
These
sulfinates
then
serve
versatile
building
blocks
for
of
diverse
sulfur-containing
organic
compounds,
including
sulfones,
sulfonamides,
sulfonate
esters.
Our
use
flow
technology
offers
robust,
safe
scalable
platform
effectively
activating
challenging
gaseous
facilitating
transformation
into
valuable
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.
ACS Catalysis,
Journal Year:
2022,
Volume and Issue:
12(17), P. 10764 - 10770
Published: Aug. 18, 2022
A
copper-catalyzed
four-component
enantioselective
arylsulfonylcyanation
of
vinylarenes
has
been
developed
that
enables
easy
access
to
a
variety
chiral
β-sulfonyl
nitriles
with
up
95%
yield
and
96%
ee.
The
reaction
utilizes
bench-stable
SO2
surrogate
(SOgen),
takes
place
under
mild
conditions,
exhibits
good
substrate
scope
functional
group
compatibility.
Control
experiments
show
the
use
SOgen
as
is
key
achieving
excellent
reactivities
enantioselectivities.
Preliminary
mechanistic
data
indicates
this
vinylarene
1,2-difunctionalization
likely
proceeds
by
radical
pathway.
exemplifies
rare
case
catalysis
involving
gaseous
SO2.
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 Chemistry Frontiers,
Journal Year:
2023,
Volume and Issue:
10(9), P. 2251 - 2256
Published: Jan. 1, 2023
We
report
an
enantioselective
sulfonylation
of
α,β-unsaturated
carbonyl
compounds
with
4-alkyl
substituted
Hantzsch
esters
and
DABCO·(SO
2
)
by
interfacing
photoredox
hydrogen
bonding
catalysis.
Angewandte Chemie International Edition,
Journal Year:
2023,
Volume and Issue:
62(46)
Published: Oct. 2, 2023
This
research
explores
the
enantioselective
hydrosulfonylation
of
various
α,β-unsaturated
carbonyl
compounds
via
use
visible
light
and
redox-active
chiral
Ni-catalysis,
facilitating
synthesis
enantioenriched
α-chiral
sulfones
with
remarkable
enantioselectivity
(exceeding
99
%
ee).
A
significant
challenge
entails
enhancing
reactivity
between
metal-coordinated
moderate
electrophilic
sulfonyl
radicals,
aiming
to
minimize
background
reactions.
The
success
our
approach
stems
from
two
distinctive
attributes:
1)
Cl-atom
abstraction
employed
for
radical
generation
chlorides,
2)
single-electron
reduction
produce
a
key
enolate
Ni-complex.
latter
process
appears
enhance
feasibility
radical's
addition
electron-rich
radical.
An
in-depth
investigation
into
reaction
mechanism,
supported
by
both
experimental
observations
theoretical
analysis,
offers
insight
intricate
process.
Moreover,
versatility
methodology
is
highlighted
through
its
successful
application
in
late-stage
functionalization
complex
bioactive
molecules,
demonstrating
practicality
as
strategy
producing
sulfones.
Green Chemistry,
Journal Year:
2023,
Volume and Issue:
25(10), P. 3857 - 3863
Published: Jan. 1, 2023
A
general
and
environmentally
friendly
organic
photo-induced
strategy
was
developed
for
the
synthesis
of
diverse
alkyl-substituted
β-amino
sulfone
derivatives,
including
primary,
secondary,
tertiary
products.
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.
