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.
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.
Nature Communications,
Год журнала:
2024,
Номер
15(1)
Опубликована: Май 27, 2024
Abstract
Herein,
we
disclose
a
highly
efficient
cobalt-catalyzed
cross-electrophile
alkynylation
of
broad
range
unactivated
chlorosilanes
with
alkynyl
sulfides
as
stable
and
practical
electrophiles.
Strategically,
employing
easily
synthesized
precursors
allows
access
to
various
alkynylsilanes
in
good
excellent
yields.
Notably,
this
method
avoids
the
utilization
strong
bases,
noble
metal
catalysts,
high
temperature
forcing
reaction
conditions,
thus
presenting
apparent
advantages,
such
substrate
scope
(72
examples,
up
97%
yield),
Csp-S
chemo-selectivity
functional
group
compatibility
(Ar-X,
X
=
Cl,
Br,
I,
OTf,
OTs).
Moreover,
utilities
are
also
illustrated
by
downstream
transformations
late-stage
modification
structurally
complex
natural
products
pharmaceuticals.
Mechanistic
studies
elucidated
that
cobalt
catalyst
initially
reacted
sulfides,
activation
occurred
via
an
S
N
2
process
instead
radical
pathway.
We
report
here
a
step-economic
and
cost-effective
cross-electrophile
coupling
of
aryl
thianthrenium
salts
with
widely
available
bromides,
which
proceeded
effectively
via
C-S
bond
activation
at
ambient
temperature
in
THF
the
presence
palladium
catalyst,
magnesium
turnings,
lithium
chloride
to
enable
facile
assembly
wide
array
structurally
diverse
biaryls
modest
good
yields
functional
group
compatibility.
In
addition,
gram-scale
reaction
could
also
be
realized.
The Journal of Organic Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Янв. 9, 2025
This
study
explores
the
deoxygenation
of
pyridine
N-oxides
and
presents
a
one-step
photoredox
method
for
direct
synthesis
2-hydroxymethylated
pyridines
from
N-oxides.
Mechanism
studies
elucidate
role
catalyst
provide
evidence
possible
electron
transfer
process
formation
key
radicals.
A
range
derivatives,
particularly
2-hydroxymethyl-substituted
pyridines,
which
may
be
difficult
to
obtain,
can
synthesized
in
single
step.
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.
Molecules,
Год журнала:
2024,
Номер
29(9), С. 1991 - 1991
Опубликована: Апрель 26, 2024
An
efficient
palladium-catalyzed
carbonylation
of
aryl
fluorosulfates
with
formates
for
the
facile
synthesis
esters
was
developed.
The
cross-coupling
reactions
proceeded
effectively
in
presence
a
palladium
catalyst,
phosphine
ligand,
and
triethylamine
DMF
to
produce
corresponding
moderate
good
yields.
Of
note,
functionalities
or
substituents,
such
as
nitro,
cyano,
methoxycarbonyl,
trifluoromethyl,
methylsulfonyl,
trifluoromethoxy,
fluoro,
chloro,
bromo,
methyl,
methoxy,
N,N-dimethyl,
[1,3]dioxolyl,
were
well-tolerated
reactions,
which
could
be
kept
late-stage
modification.
employing
readily
available
relatively
robust
coupling
electrophiles
potentially
serve
an
attractive
alternative
traditional
cross-couplings
use
halides
pseudohalides
substrates.
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(13), С. 9450 - 9461
Опубликована: Июнь 13, 2024
Visible-light-promoted
thiolation
of
benzyl
chlorides
with
thiosulfonates
is
disclosed
via
an
electron
donor-acceptor
complex
strategy.
In
addition
to
efficiently
delivering
a
series
arylbenzylsulfide
compounds,
versatile
thioglycosides
were
also
successfully
constructed
by
applying
the
metal-
and
photocatalyst-free
protocol.
Preliminary
mechanistic
studies
suggest
that
radical-radical
coupling
process
was
involved
in
this
transformation.
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
unknown
Опубликована: Авг. 30, 2024
With
the
assistance
of
nickel
as
catalyst,
2,2'-bipyridine
(bpy)
ligand,
and
manganese
reducing
metal,
reductive
amidation
isocyanates
with
readily
accessible
aryl
fluorosulfates
could
be
successfully
accomplished.
The
reactions
proceeded
effectively
via
C-O
bond
activation
in
DMF
at
room
temperature,
enabling
facile
synthesis
a
range
structurally
diverse
amides
moderate
to
high
yields
broad
functionality
compatibility.
In
addition,
synthetic
usefulness
method
was
further
demonstrated
by
applying
reaction
scale-up
late-stage
functionalization
complex
molecules
biological
activities.
