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.
Organic Letters,
Год журнала:
2024,
Номер
26(18), С. 3906 - 3910
Опубликована: Апрель 29, 2024
Sulfilimines
are
valuable
compounds
in
both
organic
synthesis
and
pharmaceuticals.
In
this
study,
we
present
a
copper-catalyzed
sulfur
alkylation
of
sulfenamides
with
A
copper-catalyzed
Ullmann-type
cross-coupling
reaction
of
sulfenamides
with
aryl
iodides
is
developed.
The
key
to
success
the
use
a
2-methylnaphthalen-1-amine-derived
amide
ligand,
which
enables
formation
an
S-C
bond
access
functionalized
sulfilimines
in
good
excellent
yields
at
room
temperature.
This
method
has
advantages
mild
conditions,
broad
substrate
scope,
functional
group
compatibility,
and
high
chemoselectivity.
utility
this
protocol
highlighted
through
late-stage
modification
drug-relevant
molecules
sulfilimine
product
derivatization.
Green Chemistry,
Год журнала:
2023,
Номер
25(22), С. 9092 - 9096
Опубликована: Янв. 1, 2023
An
efficient
iron-catalyzed
sulfur
alkylation
of
sulfenamides
with
diazo
compounds
for
the
synthesis
functionalized
sulfilimines
is
developed
under
air
conditions.
Angewandte Chemie International Edition,
Год журнала:
2023,
Номер
63(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.
Organic Letters,
Год журнала:
2024,
Номер
26(18), С. 3816 - 3821
Опубликована: Апрель 30, 2024
A
new
method
to
synthesize
o-bromobenzenethiol
equivalents
through
aryne
intermediates
is
disclosed.
Various
are
prepared
by
the
bromothiolation
of
with
potassium
xanthates.
Aryl
xanthates
serve
in
synthesis
diverse
organosulfurs
involving
phenothiazines
and
thianthrenes
further
transformations.
Abstract
Sulfur-containing
compounds
are
found
in
myriad
applications.
Sulfones
and
sulfonamides
the
most
common
functional
groups
used
medicinal
agrochemical
endeavours.
Isosteres
of
these
groups,
for
example,
sulfoximines
sulfonimidamides,
emerging
functionalities,
they
increasingly
relevant
patent
literature.
However,
general,
associated
synthetic
routes
still
have
limitations,
including
use
harsh
reaction
conditions
highly
reactive
reagents.
A
variety
catalytic
reactions
that
employ
a
diverse
range
substrate
classes
been
developed
to
address
issues.
This
short
review
highlights
recent
syntheses
aza-sulfur
compounds,
which
we
hope
will
open
new
directions
discovery
chemistry.
1
Introduction
2
Reactions
N-Sulfinylamines
3
with
Sulfenamides
4
Sulfinates
5
Sulfinamides
6
Other
Aza-Sulfur
Compounds
7
Conclusion
Organic Chemistry Frontiers,
Год журнала:
2024,
Номер
11(21), С. 6177 - 6183
Опубликована: Янв. 1, 2024
o
-Hydroxyaryl
azomethine
ylides
react
with
ethenesulfonyl
fluorides
via
a
tandem
[3
+
2]
cycloaddition–SuFEx
click
process
to
produce
sulfochromeno[4,3-
b
]pyrrolidines
in
high
yields.
The Journal of Organic Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Май 9, 2025
In
this
work,
we
report
an
electrochemical
method
for
the
straightforward
preparation
of
scarcely
accessible
sulfinimidate
esters
from
readily
available
sulfonamides,
thiophenols,
and
alcohols.
Mechanistic
experiments
show
that
sulfur
oxidation
at
anodic
surface
generates
electrophilic
intermediate,
which
subsequently
undergoes
nucleophilic
substitution.
Moreover,
sulfilimines
can
be
obtained
in
moderate-to-excellent
yields
when
thioethers
are
used
as
S-donor
instead
thiophenols
via
a
dehydrogenateive
imination
process.
This
is
also
characterized
by
mild
reaction
condition,
operational
simplicity,
high
atomic
economic
efficiency,
easy
later
drug
synthesis,
modification,
well
scaling
up
to
gram
scale.
An
aryne-promoted
dehydrosulfurization
reaction
of
thioamides
to
give
nitriles
and
diaryl
sulfides
in
a
one-pot
manner
is
presented.
Aromatic,
heteroaromatic,
aliphatic
natural
products
drug-derived
were
obtained
good
excellent
yields.
Especially,
selenoamide
was
also
suitable
substrate
produced
selenide
nitrile
high
The
D-labeled
experiments
indicated
that
the
protons
transfer
sulfides.
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.
