Beilstein Journal of Organic Chemistry,
Год журнала:
2024,
Номер
20, С. 2891 - 2920
Опубликована: Ноя. 13, 2024
Diaryliodonium
salts
have
become
widely
recognized
as
arylating
agents
in
the
last
two
decades.
Both,
symmetrical
and
unsymmetrical
forms
of
these
serve
effective
electrophilic
reagents
various
organic
syntheses.
The
use
diaryliodoniums
C–C
carbon–heteroatom
bond
formations,
particularly
under
metal-free
conditions,
has
further
enhanced
popularity
reagents.
In
this
review,
we
concentrate
on
arylation
reactions
involving
carbon
other
heteroatoms,
encompassing
rearrangement
absence
any
metal
catalyst,
summarize
advancements
made
five
years.
Organic Letters,
Год журнала:
2023,
Номер
25(27), С. 5157 - 5161
Опубликована: Июль 5, 2023
An
efficient
and
metal-free
approach
for
the
synthesis
of
sulfilimines
from
sulfenamides
with
aryne
cyclohexyne
precursors
has
been
developed.
The
reaction
proceeds
through
unusual
S–C
bond
formation,
which
offers
a
novel
practical
entry
to
access
wide
range
in
moderate
good
yields
excellent
chemoselectivity.
Moreover,
this
protocol
is
amenable
gram-scale
applicable
transformation
products
into
useful
sulfoximines.
Organic Letters,
Год журнала:
2023,
Номер
25(25), С. 4759 - 4764
Опубликована: Июнь 20, 2023
Sulfur-(hetero)arylation
of
sulfenamides
with
commercially
abundant
(hetero)aryl
iodides
by
Ullmann-type
coupling
inexpensive
copper(I)
iodide
as
the
catalyst
is
reported.
A
broad
scope
reaction
inputs
was
demonstrated,
including
both
aryl
and
alkyl
highly
sterically
hindered
5-
6-membered
ring
heteroaryl
iodides.
Relevant
to
many
bioactive
high
oxidation
state
sulfur
compounds,
(hetero)arylation
Organic Letters,
Год журнала:
2023,
Номер
25(23), С. 4335 - 4339
Опубликована: Июнь 2, 2023
Sulfilimines
are
key
intermediates
to
common
motifs
in
medicines
and
agrochemicals.
Typically,
this
class
of
compounds
prepared
by
imidation
thioethers,
transition-metal-catalyzed
or
base-promoted
sulfur
alkylation
arylation.
Here,
we
report
a
practical
efficient
base-mediated
arylation
reaction
for
the
preparation
sulfilimines.
A
wide
range
N-acyl
N-aryl
sulfenamides
react
with
various
diaryliodonium
salts
smoothly
afford
sulfilimines
high
yields
excellent
chemoselectivities.
The Journal of Organic Chemistry,
Год журнала:
2023,
Номер
88(13), С. 9352 - 9359
Опубликована: Июнь 16, 2023
A
novel
and
efficient
S-arylation
of
sulfenamides
with
diaryliodonium
salts
for
the
synthesis
sulfilimines
is
developed.
The
reaction
proceeds
smoothly
under
transition-metal-free
air
conditions,
giving
rapid
access
to
in
good
excellent
yields
via
selective
S-C
bond
formation.
This
protocol
scalable
exhibits
a
broad
substrate
scope,
functional
group
tolerance,
chemoselectivity.
Angewandte Chemie International Edition,
Год журнала:
2024,
Номер
63(37)
Опубликована: Июнь 27, 2024
Abstract
Sulfur‐containing
functional
groups
have
garnered
considerable
attention
due
to
their
common
occurrence
in
ligands,
pharmaceuticals,
and
insecticides.
Nevertheless,
enantioselective
synthesis
of
sulfilimines,
particularly
diaryl
sulfilimines
remains
a
challenging
persistent
goal.
Herein
we
report
highly
enantio‐
chemoselective
cross–coupling
sulfenamides
with
aryl
diazonium
salt
construct
diverse
S(IV)
stereocenters
by
Pd
catalysis.
Bisphosphine
ligands
bearing
sulfinamide
play
crucial
role
achieving
high
reactivity
selectivity.
This
approach
provides
general,
modular
divergent
framework
for
quickly
synthesizing
chiral
sulfoximines
that
are
otherwise
access.
In
addition,
the
origins
chemoselectivity
enantioselectivity
were
extensively
investigated
using
density
theory
calculations.
Angewandte Chemie International Edition,
Год журнала:
2023,
Номер
63(6)
Опубликована: Дек. 21, 2023
Sulfilimines,
the
aza-variants
of
sulfoxides,
are
key
structural
motifs
in
natural
products,
pharmaceuticals,
and
agrochemicals;
sulfilimine
synthesis
is
therefore
important
organic
chemistry.
However,
methods
for
radical
sulfilimination
remain
elusive,
as
a
result,
diversity
currently
available
sulfilimines
limited.
Herein,
we
report
first
protocol
decarboxylative
reactions
between
sulfenamides
N-hydroxyphthalimide
esters
primary,
secondary,
tertiary
alkyl
carboxylic
acids,
which
were
achieved
via
combination
photoredox,
copper,
Brønsted
base
catalysis.
This
novel
provided
wide
variety
sulfilimines,
addition
to
serving
an
efficient
route
S-alkyl/S-aryl
homocysteine
S-(4-methylphenyl)
sulfoximine.
Moreover,
it
could
be
used
late-stage
introduction
group
into
structurally
complex
molecules,
thereby
avoiding
need
preserve
labile
organosulfur
moieties
through
multistep
synthetic
sequences.
A
mechanism
involving
photocatalytic
substrate
transformation
copper-mediated
C(sp
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
Sulfilimines
are
versatile
synthetic
intermediates
and
important
moieties
in
bioactive
molecules.
However,
their
applications
drug
discovery
underexplored,
efficient
asymmetric
methods
highly
desirable.
Here,
we
report
a
transition
metal–free
pentanidium-catalyzed
sulfur
alkylation
of
sulfenamides
with
exclusive
chemoselectivity
over
nitrogen
high
enantioselectivity.
The
reaction
conditions
were
mild,
wide
range
enantioenriched
aryl
alkyl
sulfilimines
obtained.
utility
practicability
this
robust
protocol
further
demonstrated
through
gram-scale
reactions
late-stage
functionalization
drugs.
Organic Letters,
Год журнала:
2023,
Номер
25(39), С. 7192 - 7197
Опубликована: Сен. 21, 2023
Sulfilimines,
the
aza
analogues
of
sulfoxides,
are
increasing
interest
in
medicinal
and
agrochemical
research
programs.
However,
development
efficient
routes
for
their
synthesis
has
remained
relatively
unexplored.
In
this
study,
we
report
a
transition
metal-free,
selective
S-arylation
reaction
between
sulfenamides
arynes,
enabling
facile
preparation
structurally
diverse
sulfilimines
under
mild
redox-neutral
conditions
good
yields.
The
application
value
our
method
was
further
demonstrated
by
scale-up
synthesis,
downstream
derivatization,
robustness
screen.
The Journal of Organic Chemistry,
Год журнала:
2023,
Номер
88(16), С. 11728 - 11734
Опубликована: Июль 28, 2023
In
this
study,
we
present
a
novel,
efficient
method
for
the
oxidative
amination
of
sulfenamides
using
diacetoxyiodobenzene
(PhI(OAc)2)
and
amines
under
basic
conditions.
This
innovative
technique
streamlines
synthesis
sulfinamidines
mild,
metal-free
conditions,
achieving
outstanding
yields
up
to
99%.
Furthermore,
propose
possible
pathways
that
elucidate
observed
molecular
sequence
events
in
reaction.
cutting-edge
approach
not
only
advances
valuable
sulfinamidine
compounds
but
also
expands
synthetic
toolbox
available
chemists,
paving
way
future
discoveries
organic
potential
applications
medicinal
chemistry.
