The Journal of Organic Chemistry,
Год журнала:
2023,
Номер
88(19), С. 13418 - 13426
Опубликована: Сен. 26, 2023
A
nickel-catalyzed
cross-coupling
reaction
of
aryl
methyl
sulfides
with
bromides
has
been
developed
to
access
biaryls
in
yields
up
86%.
The
reactions
proceeded
well
using
Ni(COD)2
as
catalyst
the
ligand
BINAP
(2,2′-bis(diphenylphosphanyl)-1,1′-binaphthalene)
presence
magnesium.
method
a
broad
scope
substrates
and
is
scalable.
wide
availability
commercially
available
absence
preparation
organometallic
reagents
make
high
application
value.
Organic Chemistry Frontiers,
Год журнала:
2023,
Номер
10(20), С. 5171 - 5179
Опубликована: Янв. 1, 2023
We
report
a
cross-electrophile
coupling
of
aryl
thiols
with
bromides
via
C–S
bond
activation
instead
S–H
cleavage.
The
reaction
proceeded
effectively
in
the
presence
nickel
catalyst,
magnesium,
and
lithium
chloride
to
afford
various
biaryls
moderate
good
yields.
Molecules,
Год журнала:
2024,
Номер
29(4), С. 831 - 831
Опубликована: Фев. 13, 2024
Hydroxylation
of
aryl
sulfonium
salts
could
be
realized
by
utilizing
acetohydroxamic
acid
and
oxime
as
hydroxylative
agents
in
the
presence
cesium
carbonate
a
base,
leading
to
variety
structurally
diverse
hydroxylated
arenes
47–95%
yields.
In
addition,
reaction
exhibited
broad
functionality
tolerance,
range
important
functional
groups
(e.g.,
cyano,
nitro,
sulfonyl,
formyl,
keto,
ester)
well
amenable
mild
conditions.
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.
Organic Letters,
Год журнала:
2023,
Номер
25(13), С. 2318 - 2322
Опубликована: Март 24, 2023
A
one-pot,
direct
cross-coupling
of
aryl
fluorosulfate
with
bromide,
which
is
step-economical
and
avoids
the
use
a
preprepared/commercial
organometallic
reagent,
could
be
accomplished
by
performing
reaction
in
THF
at
room
temperature
presence
nickel
catalyst,
magnesium
turnings,
lithium
chloride,
giving
rise
to
corresponding
biaryls
moderate
good
yields
reasonable
functional
group
compatibility.
Organic Letters,
Год журнала:
2023,
Номер
25(29), С. 5525 - 5529
Опубликована: Июль 17, 2023
A
nickel-catalyzed
direct
cross-coupling
of
unactivated
aryl
fluorides
with
bromides
is
realized.
The
one-pot
reaction,
which
avoids
the
use
preformed
and
sensitive
organometallic
reagents,
proceeds
effectively
via
C-F
bond
cleavage
at
room
temperature
in
THF
presence
phosphine
ligand
magnesium
powder
(with
or
without
TMSCl)
to
produce
desired
biaryls
modest
good
yields.
Chinese Journal of Chemistry,
Год журнала:
2023,
Номер
41(24), С. 3539 - 3546
Опубликована: Авг. 19, 2023
Comprehensive
Summary
Cross‐electrophile
coupling
of
triazine
esters
with
aryl
bromides
could
be
facilely
accomplished
by
employing
nickel
as
catalyst,
magnesium
metal
mediator,
and
lithium
chloride
additive.
The
reactions
proceeded
efficiently
in
THF
at
room
temperature
through
C—O
bond
activation
to
afford
an
array
structurally
different
diaryl
ketones
moderate
good
yields
wide
functional
group
tolerance.
Control
experiments
showed
that
nickel,
magnesium,
chloride,
are
all
indispensable
for
the
performance
reaction.
Preliminary
mechanistic
exploration
indicated
situ
formed
arylmagnesium
reagent
insertion
into
bromide
might
serve
key
intermediate
cross‐coupling.
method
which
avoids
utilization
moisture‐labile
relatively
difficult‐to‐obtain
organometallics
is
step‐economical,
cost‐efficient,
operationally
simple,
potentially
serving
attractive
alternative
documented
methods.
Advanced Synthesis & Catalysis,
Год журнала:
2023,
Номер
365(15), С. 2511 - 2515
Опубликована: Июль 4, 2023
Abstract
A
step‐economical
and
operationally
simple
nickel‐catalyzed
cross‐electrophile
coupling
of
aryl
phosphates
with
bromides
through
C−O
bond
cleavage,
which
precluded
the
employment
relatively
moisture‐labile
unreadily
available
organometallics,
was
developed.
The
reaction
proceeded
smoothly
in
presence
magnesium
turnings
lithium
chloride
THF
to
afford
corresponding
biaryls
moderate
good
yields
reasonable
functionality
tolerance.
Organic Letters,
Год журнала:
2023,
Номер
26(1), С. 416 - 420
Опубликована: Дек. 31, 2023
A
reductive
amidation
of
triazine
esters
with
nitroarenes
by
using
cheap
iron
as
a
reducing
metal
in
the
presence
TMSCl
DMF
was
developed.
The
reactions
proceeded
efficiently
under
transition
metal-free
conditions
to
give
corresponding
amides
moderate
good
yields
functional
group
compatibility.
Preliminary
mechanistic
investigations
indicated
that
nitrosobenzene,
N-phenyl
hydroxylamine,
azoxybenzene,
azobenzene,
aniline,
and
N-arylformamide
possibly
served
intermediates
reaction.
