Angewandte Chemie,
Journal Year:
2023,
Volume and Issue:
136(3)
Published: Nov. 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,
Journal Year:
2024,
Volume and Issue:
26(18), P. 3906 - 3910
Published: April 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
Organic Letters,
Journal Year:
2024,
Volume and Issue:
unknown
Published: Sept. 12, 2024
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.
Synthesis,
Journal Year:
2024,
Volume and Issue:
unknown
Published: Sept. 26, 2024
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
Green Chemistry,
Journal Year:
2023,
Volume and Issue:
25(22), P. 9092 - 9096
Published: Jan. 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,
Journal Year:
2023,
Volume and Issue:
63(3)
Published: Nov. 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,
Journal Year:
2024,
Volume and Issue:
26(18), P. 3816 - 3821
Published: April 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.
The Journal of Organic Chemistry,
Journal Year:
2025,
Volume and Issue:
unknown
Published: May 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.
Organic Chemistry Frontiers,
Journal Year:
2024,
Volume and Issue:
11(21), P. 6177 - 6183
Published: Jan. 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.
Organic Letters,
Journal Year:
2024,
Volume and Issue:
unknown
Published: Aug. 30, 2024
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.
