Angewandte Chemie,
Год журнала:
2023,
Номер
136(3)
Опубликована: Ноя. 28, 2023
Abstract
A
general
one‐pot
approach
to
diverse
N
‐acylsulfenamides
from
a
common
S
‐phenethylsulfenamide
starting
material
is
reported.
This
was
demonstrated
by
C−S
bond
formation
utilizing
commercially
abundant
(hetero)aryl
iodides
and
boronic
acids
provide
sulfilimine
intermediates
that
undergo
thermal
elimination
of
styrene.
In
contrast,
all
prior
approaches
rely
on
thiol
inputs
introduce
sulfenamide
‐substituents.
broad
scope
reaction
including
for
approved
drugs
drug
precursors
with
dense
display
functionality.
Several
different
types
sulfur
functionalization
were
performed
derived
complex
precursor
the
blockbuster
anticoagulant
apixaban,
highlighting
utility
this
introduction
high
oxidation
state
groups
in
bioactive
compounds.
Mechanistic
studies
established
key
styrene
step
proceeds
concerted
does
not
require
reagents
or
catalysts,
therefore,
should
be
applicable
synthesis
electrophiles
conditions
formation.
The Journal of Organic Chemistry,
Год журнала:
2023,
Номер
89(1), С. 731 - 739
Опубликована: Дек. 14, 2023
A
selective
[4
+
2]
cycloaddition
reaction
of
thiazolo-2-pyridones
with
arynes
has
been
demonstrated.
The
developed
protocol
allows
rapid
access
to
highly
functionalized,
structurally
complex
thiazolo-fused
bridged
isoquinolones
in
high
yields,
which
are
susceptible
further
late-stage
functionalization.
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(16), С. 11766 - 11776
Опубликована: Авг. 3, 2024
A
direct
and
practical
three-component
tandem
reaction
of
arynes,
S-methyl-d3
sulfonothioate
with
sulfonamides
or
amides
is
developed.
The
highly
efficient
chemoselective,
which
allows
mild
synthesis
trideuteromethylated
sulfilimines
broad
substrate
scope
good
functional
group
compatibility,
giving
the
products
in
to
excellent
yields
92%–99%
deuterium
incorporation.
Mechanism
studies
disclosed
sulfenamide
that
generated
situ
key
intermediate
for
reaction.
This
protocol
provides
potential
method
introduction
-SCD3
moiety
deuteration
marked
drugs
drug
candidates
containing
sulfilimine
skeleton.
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
unknown
Опубликована: Сен. 12, 2024
A
simple
and
high-yielding
strategy
to
produce
a
variety
of
β-keto
sulfides
using
asymmetrical
symmetrical
thiosulfonates
with
ketones
under
mild
conditions
is
reported.
It
was
found
that
the
various
substituted
compounds,
both
electron-withdrawing
electron-donating
substituents,
afforded
wide
range
thiosulfones
(α-thioaryl-β-keto
sulfones)
in
moderate
high
yields.
The
transformations
were
reliable
at
gram-scale,
thus
illustrating
their
efficiency
practicality.
plausible
mechanism
for
protocol
also
proposed.
Angewandte Chemie,
Год журнала:
2023,
Номер
136(3)
Опубликована: Ноя. 28, 2023
Abstract
A
general
one‐pot
approach
to
diverse
N
‐acylsulfenamides
from
a
common
S
‐phenethylsulfenamide
starting
material
is
reported.
This
was
demonstrated
by
C−S
bond
formation
utilizing
commercially
abundant
(hetero)aryl
iodides
and
boronic
acids
provide
sulfilimine
intermediates
that
undergo
thermal
elimination
of
styrene.
In
contrast,
all
prior
approaches
rely
on
thiol
inputs
introduce
sulfenamide
‐substituents.
broad
scope
reaction
including
for
approved
drugs
drug
precursors
with
dense
display
functionality.
Several
different
types
sulfur
functionalization
were
performed
derived
complex
precursor
the
blockbuster
anticoagulant
apixaban,
highlighting
utility
this
introduction
high
oxidation
state
groups
in
bioactive
compounds.
Mechanistic
studies
established
key
styrene
step
proceeds
concerted
does
not
require
reagents
or
catalysts,
therefore,
should
be
applicable
synthesis
electrophiles
conditions
formation.
