Molecules,
Journal Year:
2023,
Volume and Issue:
28(23), P. 7869 - 7869
Published: Nov. 30, 2023
Both
sulfonyl
and
phosphorothioate
are
important
privileged
structural
motifs
which
widely
presented
in
pharmaceuticals
agrochemicals.
Herein,
we
describe
an
efficient
approach
to
synthesizing
sulfonyl-containing
phosphorothioates
by
merging
photoredox
copper
catalysis
at
room
temperature.
This
protocol
is
compatible
with
a
wide
range
of
substrates
can
be
applied
the
late-stage
modification
complex
molecules.
Control
experiments
conducted
demonstrate
generation
radical
transformation.
Chinese Journal of Chemistry,
Journal Year:
2024,
Volume and Issue:
42(15), P. 1679 - 1685
Published: March 15, 2024
Comprehensive
Summary
A
novel
and
eco‐friendly
electrochemical
activation
of
trifluoromethyl
thianthrenium
triflate
(TT–CF
3
+
OTf
−
)
for
trifluoromethylation
imidazole‐fused
heteroaromatic
compounds
was
established.
This
method
involves
the
direct
electrolysis
TT–CF
without
requirement
external
oxidants
or
catalysts,
aligning
with
principles
green
chemistry.
wide
range
including
imidazo[1,2‐
a
]pyridines
benzo[
d
]imidazo[2,1‐
b
]thiazoles
have
been
successfully
trifluoromethylated
using
this
technique,
exhibiting
excellent
compatibility
various
functional
groups
broad
substrate
scope.
Moreover,
method's
applicability
one‐pot
sequential
reactions
enables
reduction
waste
resource
consumption
by
eliminating
need
intermediate
purification
steps.
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.
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.
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:
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.
Advanced Synthesis & Catalysis,
Journal Year:
2024,
Volume and Issue:
366(16), P. 3450 - 3454
Published: May 31, 2024
Abstract
We
report
the
development
of
a
four‐component
electrochemical
method
for
synthesis
CF
3
‐oxazoles,
utilizing
alkynes
and
NaSO
2
in
MeCN.
The
leverages
simplicity
mildness
reaction
conditions,
despite
inherent
complexity
four
distinct
components
through
aminotrifluoromethylation
alkyne
followed
by
in‐situ
cyclization.
Notably,
addition
to
MeCN
solvent,
presence
residual
water
mixture
also
contributed
as
coupling
partner.
involves
sequence
controlled
oxidation
steps
under
constant
potential
with
graphite
electrodes,
facilitated
mediator
TMEDA,
highlighting
precision
achievable
electrochemistry.
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
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.
