Direct Cross-Couplings of Aryl Nonaflates with Aryl Bromides under Nickel Catalysis
The Journal of Organic Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Янв. 30, 2025
The
direct
cross-couplings
of
aryl
nonaflates
with
bromides
could
be
successfully
accomplished
by
utilizing
nickel
as
the
catalyst,
magnesium
metal
mediator,
and
lithium
chloride
additive.
reactions
proceeded
efficiently
in
THF
at
room
temperature
to
produce
desired
biaryls
moderate
good
yields,
showing
both
a
reasonable
substrate
scope
functional
group
tolerance.
Additionally,
an
equally
performance
realized
when
reaction
was
subjected
scale-up
synthesis.
Preliminary
study
suggested
that
presumably
proceeds
through
situ
formation
arylmagnesium
reagent
key
intermediate.
Язык: Английский
Synthesis of Polyfluorinated Biaryls via Palladium-Catalyzed Decarboxylative Cross-Coupling of Zinc Polyfluorobenzoates with Aryl Fluorosulfates
The Journal of Organic Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Апрель 11, 2025
A
palladium-catalyzed
decarboxylative
cross-coupling
of
zinc
polyfluorobenzoates
with
aryl
fluorosulfates,
which
proceeded
efficiently
via
C-O
bond
cleavage
to
afford
the
corresponding
polyfluorinated
biaryls
in
moderate-to-good
yields,
was
developed.
The
reactions
exhibited
both
good
substrate
scope
and
broad
functional
group
compatibility,
it
could
be
scaled-up
easily.
synthetic
simplicity
practicability
reaction
further
demonstrated
by
one-pot
manipulation
directly
mixing
polyfluorobenzoic
acid
Zn(OH)2
coexistence
fluorosulfate
a
palladium
catalyst
one
flask.
Further
studies
showed
that
is
more
robust
than
other
halides
pseudohalides
as
arylating
reagent,
polyfluorobenzoate
effective
polyfluoroarylating
agent
their
magnesium
potassium
counterparts.
Язык: Английский
Magnesium-Mediated Three-Component Reductive Cross-Couplings of Aryl Aldehydes, Aryl Bromides, and Aryl 2-Pyridyl Esters: An Efficient Synthesis of Diarylmethanol Esters
Tetrahedron,
Год журнала:
2025,
Номер
unknown, С. 134558 - 134558
Опубликована: Фев. 1, 2025
Язык: Английский
Zn-promoted Sandmeyer-type reductive chalcogenation of (hetero)aryl diazonium salts
Organic Chemistry Frontiers,
Год журнала:
2025,
Номер
unknown
Опубликована: Янв. 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.
Язык: Английский
Iron-Mediated One-Pot Dehydroxylative Cross-Electrophile Coupling of Alcohol with Disulfide for Thioether Synthesis by Using TCT as a Hydroxyl-Activating Agent
Organic Letters,
Год журнала:
2025,
Номер
unknown
Опубликована: Май 8, 2025
An
efficient
dehydroxythiolation
between
alcohols
and
disulfides
using
the
widely
abundant
cheapest
iron
as
a
reaction
mediator
was
developed.
The
one-pot
thiolation
proceeded
effectively
via
C-O
bond
activation
with
aid
of
cyanuric
chloride
(TCT)
hydroxyl-activating
agent
to
give
corresponding
thioethers
in
modest
excellent
yields,
displaying
both
wide
substrate
scope
(applicable
benzyl
alcohol,
allyl
primary
alkyl
alcohol)
good
functional
group
tolerance.
In
addition,
diselenide
also
proven
be
an
appropriate
for
protocol,
could
subjected
scale-up
synthesis.
Preliminary
mechanistic
examination
revealed
that
transiently
formed
TCT-derived
ether
A,
which
is
generated
situ
TCT
possibly
serves
pivotal
intermediate
cross-electrophile
thioetherification.
Язык: Английский
Iron‐Mediated Desulfonylative Cross‐Electrophile Couplings of Heteroaryl Sulfones with Thiosulfonates for Efficient Synthesis of Heteroaryl Sulfides
Chinese Journal of Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Май 28, 2025
Comprehensive
Summary
A
desulfonylative
thiolation
between
heteroaryl
sulfones
and
thiosulfonates
for
the
efficient
synthesis
of
sulfides
was
developed.
The
cross‐electrophile
couplings
proceeded
effectively
via
old
C–SO
2
bond
cleavage
new
C–S
formation
in
presence
cheapest
widely
available
iron
powder
as
mediator
under
transition
metal
catalyst‐free
conditions,
leading
to
a
wide
array
derived
from
benzo[
d
]thiazole,
]oxazole,
thiazole,
1,3,4‐thiadiazole,
1
H
‐tetrazole
modest
excellent
yields.
In
addition,
reaction
exhibited
good
functional
group
compatibility,
protocol
could
also
be
applicable
use
selenosulfonate
substrate
subjected
scale‐up
with
equal
ease.
Notably,
unreacted
readily
recovered
after
by
resorting
attracting
property
magnetic
stir
bar
iron.
Язык: Английский
Collaborative Reduction-Induced Nickel-Catalytic Selective C–S Coupling of Aryl Di/Trithiosulfonates with Aryl Halides
Organic Letters,
Год журнала:
2024,
Номер
unknown
Опубликована: Дек. 25, 2024
Metal-catalytic
conversion
of
polysulfide
reagents
is
a
major
challenge
in
organic
synthesis
due
to
its
challenging
activation
modes
multiple
S–S
bonds.
The
utilization
aryl
di-
and
trithiosulfonates
nickel-catalyzed
reductive
coupling
with
halides
has
been
unexplored.
Herein,
we
unprecedentedly
describe
PPh3
Zn-collaborative
reduction-induced
nickel-catalytic
selective
C–S
di/trithiosulfonates
access
sulfides
over
common
disulfides
or
trisulfides.
Diverse
mechanistic
studies
indicate
that
the
key
design
such
reaction
could
be
attributed
employment
MgCl2,
which
collaborate
Zn
for
improved
reduction
potential
enables
cleavage
PhSO2(S)naryl
(n
=
2,
3)
electrophilic
sulfur
species
sulfuration
controllable
fashion.
Язык: Английский