Ligand-Enabled Copper-Catalyzed Ullmann-Type S–C Bond Formation to Access Sulfilimines
Organic Letters,
Год журнала:
2024,
Номер
unknown
Опубликована: Сен. 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.
Язык: Английский
The Catalytic Synthesis of Aza-Sulfur Functional Groups
Synthesis,
Год журнала:
2024,
Номер
unknown
Опубликована: Сен. 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
Язык: Английский
Synthesis of Sulfinamidines via Iron-Catalyzed Nitrene Transfer Reaction with Sulfenamides
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
unknown
Опубликована: Ноя. 18, 2024
An
iron-catalyzed
nitrene
transfer
reaction
for
the
rapid
synthesis
of
sulfinamidines
from
readily
available
sulfenamides
is
reported.
This
method
features
mild
conditions,
short
times,
and
a
broad
substrate
scope,
allowing
preparation
variety
in
good
to
excellent
yields.
The
synthetic
utility
sulfinamidine
products
was
further
demonstrated
through
their
conversion
other
valuable
sulfur(VI)
compounds,
such
as
sulfondiimidoyl
fluorides,
sulfinamidiate
esters,
sulfonimidamides.
Preliminary
efforts
development
an
asymmetric
variant
showed
moderate
enantioselectivity.
Язык: Английский
Regioselective Synthesis of Thiazole‐5‐thione Based on [2 + 3] Annulation Trapping of α‐Keto Sulfine with Thioamide
European Journal of Organic Chemistry,
Год журнала:
2024,
Номер
unknown
Опубликована: Окт. 22, 2024
Abstract
Aiming
to
develop
novel
annulation
reactions
using
sulfine
intermediates,
we
have
established
a
regioselective
formal
[2+3]
cyclization
reaction
of
α
‐keto
sulfines
generated
from
the
elimination
arylacyl
sulfoxides
and
thioamides.
This
new
strategy
allows
for
synthesis
thiazole‐5‐thiones
directly
without
catalysts
or
additives.
The
approach
features
step‐economic,
one‐pot
characteristics
via
tandem
sequence
in
situ
generation,
regiospecifically
nucleophilic
attack
[3+2]
cyclizatoin,
dithioate
(S=C−S−)
skeletons
formation,
subsequent
intramolecular
cyclization.
also
represents
method
constructing
skeletons.
Язык: Английский
Copper-catalyzed S-vinylation of sulfenamides for the synthesis of α,β-unsaturated sulfilimines
Cell Reports Physical Science,
Год журнала:
2024,
Номер
unknown, С. 102304 - 102304
Опубликована: Ноя. 1, 2024
Язык: Английский
Base-Promoted Sulfur Arylation of Sulfenamides to Oxonium Aryne Precursors: Chemoselective Synthesis of Sulfilimines and o-Sulfanylanilines
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
unknown
Опубликована: Дек. 16, 2024
In
this
study,
a
metal-free
and
efficient
method
for
the
synthesis
of
sulfilimines
o-sulfanylanilines
in
high
yields
with
excellent
chemoselectivities
from
oxonium
aryne
precursors
sulfenamides
has
been
developed.
This
features
mild
reaction
conditions,
simple
operations,
general
substrate
scope,
good
tolerance
functional
groups.
addition,
scale-up
synthesis,
related
applications,
preliminary
mechanistic
explorations
were
also
investigated.
Язык: Английский