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.
Chemistry - A European Journal,
Год журнала:
2024,
Номер
30(48)
Опубликована: Июнь 24, 2024
Abstract
Sulfilimines
and
their
derivatives
have
garnered
considerable
interest
in
both
synthetic
medicinal
chemistry.
Photochemical
nitrene
transfer
to
sulfides
is
known
as
a
conventional
approach
sulfilimines.
However,
the
existing
methods
limited
substrate
scope
stemming
from
incompatibility
of
singlet
intermediates
with
nucleophilic
functional
groups.
Herein,
we
report
synthesis
N
‐sulfonyl
sulfilimines
via
visible‐light‐mediated
energy
sulfonyl
azides,
uncovering
previously
overlooked
reactivity
triplet
nitrenes
sulfides.
This
reaction
features
broad
group
tolerance,
water
compatibility,
amenability
late‐stage
functionalization
drugs.
Thus,
this
work
represents
an
important
example
chemistry
that
overcomes
challenges
traditional
methods.
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(22), С. 16426 - 16432
Опубликована: Окт. 31, 2024
We
develop
a
rapid
and
mild
protocol
to
access
sulfonimidoyl
fluoride-[S(VI)]
from
sulfenamide-[S(II)]
directly.
The
transformation
occurs
via
the
reaction
of
sulfenamide
with
NCS
(N-chlorosuccinimide),
water,
TBAF
in
acetonitrile.
Water
act
as
source
for
S═O
bond
formation
fluoride,
respectively.
takes
very
short
time
(within
5
min).
drug
molecules,
such
Carbamazepine
Levetiracetam
attached
fluorides
are
also
achieved
following
this
protocol.
Furthermore,
fluoride
is
transformed
into
sulfonimidamide
presence
AlCl3.
To
best
our
knowledge,
it
first
report
detailing
synthesis
directly
S(II)-sulfenamide.
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.
