The Journal of Organic Chemistry,
Год журнала:
2023,
Номер
89(1), С. 778 - 783
Опубликована: Дек. 14, 2023
A
base
(Et3N)-promoted
synthesis
of
1,4-diarylisothiazolones
from
α-keto-N-acylsulfoximines
has
been
achieved.
The
reaction
proceeds
via
α-hydrogen
abstraction
sulfoximine,
followed
by
an
intramolecular
nucleophilic
attack
at
the
keto
carbonyl
to
form
a
tert-hydroxy
isothiazolone
intermediate.
1,4-substituted
is
obtained
after
dehydration
E1cB
path.
This
one-pot
isothiazolinones
broad
substrate
scope,
high
atom
economy,
and
provides
products
with
good
yields.
ΔELUMO–HOMO
calculated
using
Gaussian
16
B3LYP/6-31G(d,p)
level
theory.
Chemical Communications,
Год журнала:
2023,
Номер
59(19), С. 2779 - 2782
Опубликована: Янв. 1, 2023
N
-Iodosuccinimide
catalyzed,
visible-light-induced
oxidative
decarboxylative
cross-coupling
between
cinnamic
acids
and
NH-sulfoximines
leading
to
α-keto-
-acyl
sulfoximines
is
presented.
Organic Letters,
Год журнала:
2023,
Номер
25(6), С. 1025 - 1029
Опубликована: Фев. 3, 2023
Herein,
we
report
a
photoinduced
sulfoximine-to-copper
charge-transfer-enabled
generation
of
sulfoximinyl
radicals
directly
from
NH-sulfoximines
for
C-H
sulfoximination
arenes
via
radical
addition.
Through
copper-LMCT,
N-arylation
was
achieved
the
first
time
using
different
electronic
structures
as
aryl
donors.
Organic & Biomolecular Chemistry,
Год журнала:
2024,
Номер
22(10), С. 2012 - 2020
Опубликована: Янв. 1, 2024
N
-Trifluoromethylthio
sulfoximines
were
oxidized
using
NaOCl·5H
2
O
to
the
corresponding
novel
-trifluoromethylsulfaneylidene
in
high
yields
and
with
excellent
green
metrics.
Organic Letters,
Год журнала:
2022,
Номер
24(14), С. 2733 - 2737
Опубликована: Апрель 4, 2022
A
metal-,
base-,
and
additive-free
N-acylation
of
sulfoximines
was
developed
under
mild
conditions
using
organic
photoredox
catalyst.
This
green
strategy
featured
broad
substrate
scope,
good
compatibility
with
air,
high
yields
(up
to
96%).
It
could
be
further
applied
amino
acid
modifications
α-keto
N-acyl
sulfoximine
synthesis
without
any
complicated
transformations
or
operations.
The Journal of Organic Chemistry,
Год журнала:
2022,
Номер
87(16), С. 10684 - 10697
Опубликована: Авг. 8, 2022
A
tetrabutylammonium
tribromide-mediated
three-component
reaction
of
alkenes,
diselenides,
and
sulfoximines
has
been
established
herein,
providing
direct
metal-free
access
to
diverse
β-arylseleno
sulfoximine
derivatives.
This
regioselective
sulfoximido-selenization
protocol
proceeds
efficiently
under
mild
ambient
conditions
with
generally
good
yields.
strategy
is
featured
by
step
atom
economy,
practicability,
a
broad
substrate
scope,
gram-scale
synthesis.
Chemistry - A European Journal,
Год журнала:
2023,
Номер
30(9)
Опубликована: Ноя. 22, 2023
Abstract
Developed
here
is
a
robust
electrochemical
cross‐coupling
reaction
between
aroyl
hydrazine
and
NH
‐sulfoximine
via
concomitant
cleavage
formation
of
C(sp
2
)−N
bonds
with
the
evolution
H
N
as
innocuous
by‐products.
This
sustainable
protocol
avoids
use
toxic
reagents
occurs
at
room
temperature.
The
proceeds
generation
an
sulfoximidoyl
radical
anodic
oxidation
under
constant
current
electrolysis
(CCE),
affording
‐aroylated
sulfoximine.
strategy
applied
to
late‐stage
sulfoximidation
L‐menthol,
(−)‐borneol,
D‐glucose,
vitamin‐E
derivatives,
marketed
drugs
such
probenecid,
ibuprofen,
flurbiprofen,
ciprofibrate,
sulindac.
In
addition,
present
methodology
mild,
high
functional
group
tolerance
broad
substrate
scope
scalable.
Chemical Communications,
Год журнала:
2022,
Номер
58(80), С. 11312 - 11315
Опубликована: Янв. 1, 2022
A
catalytic
oxidative
addition
of
sulfoximines
to
naphthoquinones
via
C-H
functionalization
has
been
achieved
using
an
iron
system,
which
exhibits
good
reactivity
and
high
regioselectivity
in
the
presence
visible
light.
This
is
first
report
offering
efficient
protocol
for
obtaining
(naphtho)quinone-sulfoximine
hybrid
analogs
moderate
yields
with
wide
scope
both
substrates.
also
applied
on
natural
products
their
modification,
including
vitamin
K3,
Juglone
some
other
modified
scaffolds
as
well.
