Electrooxidative S-Sulfoximination of Sulfenamide: A Metal-/Catalyst-Free Green Approach
Padma Priya V. R,
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S. Sugapriya,
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Antony Haritha Mercy A
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et al.
ACS Sustainable Chemistry & Engineering,
Journal Year:
2025,
Volume and Issue:
unknown
Published: Jan. 15, 2025
Herein,
we
present
a
metal-/catalyst-free,
novel
approach
for
S-sulfoximination
of
sulfenamide.
The
electrooxidative
reactions
sulfenamides
and
sulfoximines
are
fast,
high-yielding,
atom-economical
(99.5%),
broad-substrate-tolerant,
free
from
supporting
electrolytes.
protocol
is
ecofriendly
shows
wider
substrate
tolerance
than
previous
reports.
drug-attached
sulfenamide
(levetiracetam)
sulfoximine
(albendazole)
also
undergo
the
reaction
efficiently.
A
possible
mechanistic
pathway
proposed.
Fascinatingly,
target
products
obtained
via
photochemical
in
presence
photocatalyst
eosin
Y.
Language: Английский
Regioselective N-arylation of N-Acylsulfenamides Enabled by o-Quinone Diimides
Organic Letters,
Journal Year:
2025,
Volume and Issue:
unknown
Published: Feb. 27, 2025
The
functionalization
of
N-acylsulfenamides
is
a
research
focus
in
organosulfur
chemistry,
as
the
N-S
array
has
unique
properties
and
versatile
applications.
Although
great
progress
been
made
S-functionalization,
N-functionalization,
especially
N-arylation
N-acylsulfenamides,
rarely
explored
because
lower
nucleophilicity
N-site.
Herein,
we
report
Brønsted
acid-catalyzed
regioselective
reaction
with
o-quinone
diimides.
Under
mild
metal-free
conditions,
wide
range
N-arylated
have
prepared
good
yields
excellent
regioselectivity.
ease
gram-scale
synthesis
transformations
into
useful
sulfonamides
demonstrates
their
synthetic
practicality.
Language: Английский
Visible-Light-Mediated Copper-Catalyzed S-Arylation of Sulfenamides with Aryl Thianthrenium Salts
Xiangyu Zhuang,
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Hao Li,
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Zhaoyu Feng
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et al.
Organic Letters,
Journal Year:
2025,
Volume and Issue:
unknown
Published: May 2, 2025
The
site-selective
incorporation
of
sulfilimine
functionalities
into
aromatic
compounds
provides
a
vital
strategy
for
drug
discovery
in
medicinal
chemistry.
However,
green
and
sustainable
methods
realizing
the
goal
are
still
limited.
Here,
we
report
copper-catalyzed
S-arylation
sulfenamides
with
aryl
thianthrenium
salts
irradiated
by
visible
light
without
photocatalyst,
which
exhibited
fine
functional-group
compatibility
gave
desired
products
high
yields.
Mechanistic
investigations
revealed
that
key
to
achieving
these
results
is
generation
an
electron
donor-acceptor
(EDA)
complex
between
under
basic
conditions.
Language: Английский
Heteroarylation of Sulfenamides for Modular Synthesis of Antimicrobial Sulfilimines via Sulfinimidoyl Fluoride Intermediates
Chunyan Jian,
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Xuan Huang,
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Hongyan Long
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et al.
Organic Letters,
Journal Year:
2025,
Volume and Issue:
unknown
Published: May 20, 2025
We
herein
disclose
a
mild
metal-free
strategy
for
the
construction
of
heteroaryl-derived
sulfilimines.
Central
to
this
approach
is
in
situ
generated
sulfinimidoyl
fluoride
intermediate
that
exhibits
an
optimal
balance
reactivity
and
stability
efficient
S(IV)-derived
SuFEx
reactions
with
heteroarenes
without
Lewis
acids
or
base
additives.
This
protocol
enables
rapid
incorporation
broad
range
afford
diverse
sulfilimine
scaffolds
potent
antimicrobial
activities
against
plant
pathogens.
Language: Английский
Recent advances in haloarene synthesis by aryne reactions
Shinya Tabata,
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Suguru Yoshida
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Tetrahedron Chem,
Journal Year:
2025,
Volume and Issue:
unknown, P. 100136 - 100136
Published: May 1, 2025
Language: Английский
A Rapid, Mild and Direct Route to Sulfonimidoyl Fluoride from Sulfenamide
Padma Priya V. R,
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Antony Haritha Mercy A,
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N. Kannan
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et al.
The Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
89(22), P. 16426 - 16432
Published: Oct. 31, 2024
We
develop
a
rapid
and
mild
protocol
to
access
sulfonimidoyl
fluoride-[S(VI)]
from
sulfenamide-[S(II)]
directly.
The
transformation
occurs
via
the
reaction
of
sulfenamide
with
NCS
(N-chlorosuccinimide),
water,
TBAF
in
acetonitrile.
Water
act
as
source
for
S═O
bond
formation
fluoride,
respectively.
takes
very
short
time
(within
5
min).
drug
molecules,
such
Carbamazepine
Levetiracetam
attached
fluorides
are
also
achieved
following
this
protocol.
Furthermore,
fluoride
is
transformed
into
sulfonimidamide
presence
AlCl3.
To
best
our
knowledge,
it
first
report
detailing
synthesis
directly
S(II)-sulfenamide.
Language: Английский
Trideuteromethylthiolation through Reaction of Arynes, S-Methyl-d3 Sulfonothioate with Sulfonamides or Amides: Access to Trideuteromethylated Sulfilimines
Yuping Luo,
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Xiujuan He,
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Yike Jiang
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et al.
The Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
89(16), P. 11766 - 11776
Published: Aug. 3, 2024
A
direct
and
practical
three-component
tandem
reaction
of
arynes,
S-methyl-d3
sulfonothioate
with
sulfonamides
or
amides
is
developed.
The
highly
efficient
chemoselective,
which
allows
mild
synthesis
trideuteromethylated
sulfilimines
broad
substrate
scope
good
functional
group
compatibility,
giving
the
products
in
to
excellent
yields
92%–99%
deuterium
incorporation.
Mechanism
studies
disclosed
sulfenamide
that
generated
situ
key
intermediate
for
reaction.
This
protocol
provides
potential
method
introduction
-SCD3
moiety
deuteration
marked
drugs
drug
candidates
containing
sulfilimine
skeleton.
Language: Английский