Synthesis of Thioethers via Nickel-Catalyzed Cross-Coupling of Aryl Halides with Ketene Dithioacetal
Organic Letters,
Год журнала:
2025,
Номер
unknown
Опубликована: Фев. 9, 2025
Herein,
we
present
a
nickel-catalyzed
C–S
cross-coupling
between
aryl
halides
and
ketene
dithioacetals
under
"base-free"
conditions
without
an
exogenous
ligand.
By
employing
easily
available
as
sulfide
donors,
this
reaction
affords
broad
range
of
unsymmetrical
alkyl-aryl
sulfides
using
odorous
toxic
thiols.
The
newly
developed
catalytic
methodology
features
excellent
functional
group
tolerance,
wide
substrate
scope,
diverse
downstream
synthesis.
Preliminary
mechanism
investigations
reveal
that
Ni(I)/Ni(III)
cycle
might
be
involved.
Язык: Английский
Chromium‐Catalyzed Reductive Cross‐Coupling to Construct C−SS Bonds from Unactivated Alkyl Electrophiles
Chao‐Peng Zhang,
Tian‐Zhang Wang,
Kang Wu
и другие.
ChemCatChem,
Год журнала:
2024,
Номер
16(15)
Опубликована: Март 15, 2024
Abstract
Low‐valent
chromium
catalysts
are
cheap
and
less
toxic
compared
to
other
transition
metal
catalysts.
Here
in,
we
reported
a
ligand‐free
chromium(III)‐catalyzed
manganese
reductive
cross‐coupling
of
unactivated
alkyl
electrophiles,
such
as
sulfonates
chlorides,
with
trisulfide
dioxides
thiolation
agents
form
carbon−sulfur
bonds.
The
powerful
method
featured
ample
substrate
scope
wide
functional
group
tolerance,
constructing
large
number
unsymmetrical
disulfides
under
simple
conditions.
Язык: Английский
Photo-induced decarboxylative C-S bond formation to access sterically hindered unsymmetric S-alkyl thiosulfonates and SS-alkyl thiosulfonates
Nature Communications,
Год журнала:
2024,
Номер
15(1)
Опубликована: Авг. 25, 2024
Due
to
the
high
reactivity
and
versatility
of
benzenesulfonothioates,
significant
advancements
have
been
made
in
constructing
C-S
bonds.
However,
there
are
certain
limitations
synthesis
S-thiosulfonates
SS-thiosulfonates,
especially
when
dealing
with
substantial
steric
hindrance,
which
poses
a
challenge.
Herein,
we
present
an
innovative
approach
for
assembling
unsymmetric
SS-thiosulfonates
through
integration
dual
copper/photoredox
catalysis.
Moreover,
also
realized
one-pot
strategy
by
directly
using
carboxylic
acids
as
raw
materials
in-situ
activation
them
access
without
further
purification
presynthesis
NHPI
esters.
The
envisaged
utilization
these
reagents
poised
pioneer
pathway
fabricating
versatile
spectrum
mono-,
di-,
polysulfide
compounds.
Furthermore,
they
introduce
class
potent
sulfenylating
reagents,
empowering
intricate
unsymmetrical
disulfides
that
were
previously
challenging
access.
conventional
method
synthesizing
thioether
compounds
typically
relies
on
thiol,
disulfide,
sulfinyl
halide
initial
substances,
suffering
from
strong
odors,
limited
availability,
issues.
Here,
authors
catalysis
Язык: Английский
Cross-Electrophile Couplings of Benzyl Sulfonium Salts with Thiosulfonates via C–S Bond Activation
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(18), С. 13601 - 13607
Опубликована: Сен. 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.
Язык: Английский
Synthesis of 2-Organoselenyl Quinolines via Electro-Oxidative Selenocyclization of Isocyanides
The Journal of Organic Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Март 12, 2025
Organoselenium
compounds
and
quinolines
are
widely
used
in
drugs
materials.
Herein,
we
report
an
electro-oxidative
cyclization
between
isocyanides
diselenides
to
effectively
synthesize
2-organoselenyl
a
simple
undivided
cell
without
transition-metal
catalysts
or
toxic
oxidants.
Gram-scale
synthesis
postsynthetic
modifications
highlighted
the
practicality
of
this
electrochemical
strategy.
A
series
produced
with
up
82%
yield,
good
functional
group
tolerance
high
atom
efficiency
under
room
temperature.
Язык: Английский
One-Pot Stepwise Dechalcogenization of Trisulfides to Unsymmetrical Dialkyl Thioethers
Organic Letters,
Год журнала:
2025,
Номер
unknown
Опубликована: Апрель 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
Язык: Английский
Selenosulfones, a Meetup of Chalcogens: A Journey Into Their Recent Chemistry
European Journal of Organic Chemistry,
Год журнала:
2024,
Номер
27(23)
Опубликована: Апрель 25, 2024
Abstract
A
mini
review
focused
on
the
chemistry
of
selenosulfones
reported
since
2019
is
here
presented.
Initially,
methods
aimed
to
preparation
such
moiety
are
discussed.
Successively
1,2‐,
1,3‐,
1,4‐
and
1,7‐addition
reactions
C−C
single
multiple
bonds
illustrated.
The
forth
chapter
focuses
electrophilic
aromatic
substitutions.
fifth
deals
with
C−H
functionalizations
while
sixth
one
shows
aryl
diazonium
salts
or
its
precursors.
radical
coupling
redox
active
reagents,
subject
section
seventh.
Selenosulfones
challenged
in
nucleophilic
substitutions
phosphorus‐containing
compounds
shown
eight
nine
followed
by
conclusions
perspectives
section.
Язык: Английский
Copper(0)-Catalyzed Reductive Coupling of Disulfurating Reagents and (Hetero)aryl/Alkyl Halides
Organic Letters,
Год журнала:
2024,
Номер
unknown
Опубликована: Сен. 18, 2024
Herein,
we
reported
a
copper(0)-catalyzed
reductive
coupling
of
disulfurating
reagents
and
(hetero)aryl/alkyl
halides.
Copper(0)
can
be
directly
inserted
into
tetrasulfide
then
undergoes
with
(hetero)aryl
Iodides
to
construct
disulfide.
The
method
features
the
unprecedented
use
(tetrasulfides)
in
cross-coupling
chemistry
is
convenient
broad
substrate
scopes,
even
applicable
different
halogenated
hydrocarbons.
It
worth
noting
that
methodology
practical
late-stage
modification
bioactive
scaffolds
pharmaceuticals.
In
meantime,
synthesis
disulfides
successfully
achieved
on
gram
scale,
indicating
approach
highly
valuable.
Язык: Английский
Iodine/TBHP‐Promoted Cross Coupling of N‐Hydroxy Aryl Sulfonamides and Disulfides to Synthesize Unsymmetrical Thiosulfonates
ChemistrySelect,
Год журнала:
2024,
Номер
9(46)
Опубликована: Дек. 1, 2024
Abstract
An
efficient
and
novel
method
has
been
developed
for
the
synthesis
of
structurally
diverse
unsymmetrical
thiosulfonates
via
oxidative
coupling
reactions
N
‐hydroxy
aryl
sulfonamides
disulfides.
The
iodine
TBHP
system
enables
transformations
to
afford
a
variety
with
good
high
yields.
Furthermore,
large‐scale
practical
application
access
sulfonamide
have
investigated.
Notably,
present
protocol
offers
easily
accessible
materials,
wide
range
substrates,
radical
pathways,
metal‐free
conditions.
Язык: Английский