Metal-catalyzed Thiomethylation of Chloroarenes and Diverse Aryl Electrophiles
Chemical Science,
Год журнала:
2025,
Номер
unknown
Опубликована: Янв. 1, 2025
In
this
study,
we
report
the
first
development
of
metal
catalyzed
methylthiolation
chloroarenes
and
diverse
aromatic
electrophiles,
addressing
persistent
challenges
catalyst
intermediate
deactivation
in
functionalization
less
reactive
substrates.
To
overcome
these
issues,
designed
a
novel
anion-shuttle-type
agent,
4-((methylthio)methyl)morpholine,
which
enables
controlled
situ
release
methylthiolate
anions,
thereby
preventing
poisoning
enhancing
reactivity.
This
strategy
allows
efficient
not
only
but
also
broad
range
aryl
including
bromoarenes,
triflates,
tosylates,
pivalates,
nitriles,
carboxylic
acids.
The
developed
system
exhibits
excellent
functional
group
compatibility,
making
it
applicable
to
derivatization
pharmaceuticals
natural
products.
Furthermore,
detailed
mechanistic
investigations
revealed
key
factors
underlying
exceptional
efficiency
providing
new
insights
into
C-S
bond
formation
under
practical
conditions.
Язык: Английский
Polyoxometalate-based ionic liquids: efficient reversible phase transformation-type catalysts for thiolation of alcohols to construct C–S bonds
Dalton Transactions,
Год журнала:
2024,
Номер
53(10), С. 4492 - 4500
Опубликована: Янв. 1, 2024
[PIMPS]
3
PW
12
O
40
was
used
as
a
reversible
phase
transformation-type
catalyst
for
the
thiolation
of
alcohols
to
synthesize
series
benzyl
thioethers
and
exhibited
high
activity
good
recyclability.
Язык: Английский
Nickel-Catalyzed Cross-Electrophile Vinylation of α-Chloro Phosphonates
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(21), С. 15822 - 15833
Опубликована: Окт. 18, 2024
Herein,
we
report
a
general
and
efficient
Ni-catalyzed
reductive
cross-coupling
reaction
of
substituted
vinyl
bromides
α-chloro
phosphonates
to
access
set
α-vinyl
using
zinc
as
the
terminal
reductant.
This
exhibits
broad
substrate
adaptability
good
functional
group
tolerance,
which
allows
afford
diverse
compounds
including
structurally
complex
motifs
from
natural
products
drugs.
Furthermore,
practicality
was
certificated
through
gram-scale
transformation
experiments.
The
preliminary
mechanistic
investigations
support
radical
chain
process.
potential
realize
enantiomeric
control
makes
it
more
valuable
for
further
exploration.
Язык: Английский
CuI-catalyzed regioselective hydrothiolation of alkynes: a thiol-free route to (Z)-β-alkenyl sulfides
Organic & Biomolecular Chemistry,
Год журнала:
2023,
Номер
22(3), С. 561 - 567
Опубликована: Дек. 16, 2023
A
thiol-free
procedure
for
regioselective
preparation
of
(
Язык: Английский
Synthesis of Benzyl Thioethers by C−S Coupling of Benzylic Trimethylammonium Salts and Sulfonyl Chlorides
Xiujuan Ma,
Haoyu Jin,
Min Zeng
и другие.
European Journal of Organic Chemistry,
Год журнала:
2023,
Номер
26(43)
Опубликована: Авг. 24, 2023
Abstract
A
facile
and
efficient
method
to
synthesize
thioethers
from
sulfonyl
chlorides
benzylic
trimethylammonium
salts
is
presented.
This
protocol
provides
a
simple
direct
approach
realize
the
reductive
coupling
reaction
of
readily
available
with
benzyl
ammonium
in
presence
triphenylphosphine
along
base
via
C−N
cleavage
salts.
features
mild
conditions
good
substrate
compatibility
afford
moderate
yields.
Язык: Английский
Modular Synthesis of Tetrasubstituted Vinyl Sulfides via One-Pot Sequential Carbene Transfer Reaction from Thiols with α-Diazo Carbonyl Compounds
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(15), С. 11003 - 11008
Опубликована: Июль 17, 2024
We
present
a
one-pot
reaction
that
offers
an
efficient
approach
to
synthesizing
tetrasubstituted
vinyl
sulfides
with
high
stereoselectivity.
This
method
involves
the
sequential
Wolff
rearrangement,
ylide
formation,
and
[1,4]-aryl
transfer
by
utilizing
aryl
alkyl
thiols
α-diazo
carbonyl
compounds
as
substrates.
Notably,
this
features
commercially
available
materials,
straightforward
operation,
atom
economy,
broad
substrate
scope.
Moreover,
primary
photophysical
properties
(aggregation-induced
emission
effect)
of
products
were
also
investigated,
which
might
be
useful
in
functional
materials
via
structural
modification.
Язык: Английский