Cross-Electrophile Couplings of Benzyl Sulfonium Salts with Thiosulfonates via C–S Bond Activation
Xuan-Bo Hu,
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Yuwei Chen,
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Chenlong Zhu
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et al.
The Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
89(18), P. 13601 - 13607
Published: Sept. 4, 2024
A
zinc-mediated
cross-electrophile
coupling
of
benzyl
sulfonium
salts
with
thiosulfonates
via
C-S
bond
cleavage
was
achieved.
The
reductive
thiolation
proceeded
well
under
transition
metal-free
conditions
to
afford
the
desired
sulfides
in
good
yields,
exhibiting
both
broad
substrate
scope
and
functionality
tolerance.
In
addition,
reaction
could
be
applied
use
selenosulfonate
as
an
effective
selenylation
agent
subjected
scale-up
synthesis.
Language: Английский
Radical 1,3-Hydrosulfonylation of Vinyldiazo Compounds with Sulfinyl Sulfones
Tian Jing,
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Yuan‐Li Ding,
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Wanting Fu
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et al.
Organic Letters,
Journal Year:
2025,
Volume and Issue:
unknown
Published: Feb. 4, 2025
Sulfinyl
sulfones,
as
high-valence
sulfurization
reagents,
are
widely
used
to
assemble
sulfur
sources
on
carbon
skeletons,
such
one-,
two-,
and
four-carbon
synthons,
access
organosulfur
compounds.
However,
their
reaction
with
three-carbon
synthons
has
remained
a
mystery
until
now.
We
report
here
radical
1,3-hydrosulfonylation
of
vinyldiazo
compounds
sulfinyl
sulfones.
This
not
only
represents
the
first
example
sulfones
but
also
opens
up
application
in
monofunctionalization.
Language: Английский
Zn-promoted Sandmeyer-type reductive chalcogenation of (hetero)aryl diazonium salts
Qiujin Fan,
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Yanchuang Zhao,
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Junhong Wang
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et al.
Organic Chemistry Frontiers,
Journal Year:
2025,
Volume and Issue:
unknown
Published: Jan. 1, 2025
In
this
report,
we
describe
a
nickel-free,
zinc-induced
reductive
coupling
between
(hetero)aryl
diazonium
salts
and
electrophilic
chalcogen
species
under
mild
reaction
conditions.
Language: Английский
One-Pot Stepwise Dechalcogenization of Trisulfides to Unsymmetrical Dialkyl Thioethers
Jiuwen Xu,
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Ying Chen,
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Weidong Rao
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et al.
Organic Letters,
Journal Year:
2025,
Volume and Issue:
unknown
Published: April 17, 2025
The
construction
of
C-S
bonds
has
garnered
significant
interest
due
to
the
ubiquitous
presence
organosulfur
compounds
in
natural
products
and
bioactive
molecules.
Herein,
we
report
a
one-pot,
stepwise
desulfuration
strategy
employing
trisulfides
as
precursors
for
synthesis
unsymmetrical
dialkylthioethers.
Our
study
demonstrates
that
copper
powder
facilitates
conversion
into
disulfides,
which
subsequently
undergo
nickel-catalyzed
reductive
coupling
afford
desired
products.
This
approach
provides
practical,
odorless,
broadly
applicable
method
Language: Английский
Bifunctionalization of α-Bromophenone: An Access to Functionalized β-Keto Thiosulfones
Xiaoqing Wen,
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Mengxin Li,
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Xiaoyan Peng
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et al.
The Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
unknown
Published: Sept. 12, 2024
A
simple
and
high-yielding
strategy
to
produce
a
variety
of
β-keto
sulfides
using
asymmetrical
symmetrical
thiosulfonates
with
ketones
under
mild
conditions
is
reported.
It
was
found
that
the
various
substituted
compounds,
both
electron-withdrawing
electron-donating
substituents,
afforded
wide
range
thiosulfones
(α-thioaryl-β-keto
sulfones)
in
moderate
high
yields.
The
transformations
were
reliable
at
gram-scale,
thus
illustrating
their
efficiency
practicality.
plausible
mechanism
for
protocol
also
proposed.
Language: Английский