Nature Communications,
Год журнала:
2022,
Номер
13(1)
Опубликована: Ноя. 3, 2022
The
development
of
novel
methodologies
for
the
introduction
sulfoxonium
group
under
mild
conditions
is
appealing
but
remains
underexplored.
Herein
we
report
synthesis
a
class
hypervalent
iodine
reagents
with
transferrable
group.
These
compounds
enable
mixed
iodonium-sulfoxonium
ylide
reactivity.
well-defined
are
examined
in
visible-light-promoted
cyclization
reactions
wide
range
unsaturated
bonds
including
alkenes,
alkynes,
nitriles,
and
allenes.
Two
distinct
pathways
identified,
which
controlled
by
substituent
bond.
cycloaddition
protocol
features
simple
operation,
reaction
conditions,
excellent
functional
tolerance,
affording
broad
sulfoxonium-containing
cyclic
structures
moderate
to
yields.
Furthermore,
sufoxonium
product
can
be
transformed
into
diverse
groups
structural
motifs
via
single
electron
transfer
transition-metal
catalysis.
Organic & Biomolecular Chemistry,
Год журнала:
2020,
Номер
18(43), С. 8793 - 8809
Опубликована: Янв. 1, 2020
Sulfur
ylides
first
disclosed
in
1930
started
to
gain
more
attention
the
1960s,
thanks
mainly
studies
by
Corey
and
Chaykovsky
on
their
use
for
preparation
of
strained
rings.
More
recently,
chemistry
these
compounds
has
experienced
important
growth,
part
due
similarity
reactivities
with
diazo
compounds.
This
short
review
provides
an
overview
great
assortment
reactions
sulfoxonium
ylides,
outlining
a
comparison
between
congeners:
sulfonium
Insertion
reactions,
cyclisation
ring-opening
are
highlighted,
giving
particular
catalytic
asymmetric
methodologies.
Chemical Science,
Год журнала:
2021,
Номер
13(5), С. 1192 - 1209
Опубликована: Дек. 8, 2021
Sulfoxonium
ylides
are
important
surrogates
for
diazo
compounds,
and
their
use
in
industry
as
safer
alternatives
has
been
evaluated
during
recent
years.
Beyond
the
known
classical
transformations,
these
have
also
used
a
surprising
plethora
of
novel
intrinsic
chemical
reactions,
especially
Bench
stability
handling
an
advantage
this
class
organosulfur
molecules.
Despite
this,
efficient
asymmetric
specifically
catalytic
enantioselective
versions,
only
recently
reported,
there
specific
reasons
this.
This
perspective
article
covers
topic
from
first
studies
up
to
latest
advances,
giving
personal
perspectives
showing
main
challenges
area
coming
Chemical Science,
Год журнала:
2021,
Номер
12(48), С. 15790 - 15801
Опубликована: Янв. 1, 2021
Transition-metal-catalysed
carbene
insertion
reaction
is
a
straightforward
and
efficient
protocol
for
the
construction
of
carbon–carbon
or
carbon–heteroatom
bonds.
Chemical Communications,
Год журнала:
2023,
Номер
59(26), С. 3812 - 3820
Опубликована: Янв. 1, 2023
Tetracoordinate
boron
compounds
are
a
highly
important
class
of
molecules,
which
the
key
intermediates
in
many
organoboron-related
chemical
transformations
and
have
unique
luminescence
properties.
Angewandte Chemie International Edition,
Год журнала:
2020,
Номер
59(36), С. 15554 - 15559
Опубликована: Апрель 30, 2020
Abstract
The
first
example
of
enantioselective
S−H
insertion
reactions
sulfoxonium
ylides
is
reported.
Under
the
influence
thiourea
catalysis,
excellent
levels
enantiocontrol
(up
to
95
%
ee
)
and
yields
97
%)
are
achieved
for
31
examples
in
aryl
thiols
α‐carbonyl
ylides.
Organic Letters,
Год журнала:
2021,
Номер
23(3), С. 1038 - 1043
Опубликована: Янв. 21, 2021
A
ruthenium-catalyzed
highly
chemoselective
N-alkylation
of
2-pyridones
has
been
developed,
affording
N-alkylated
2-pyridone
derivatives
in
good
yields
and
excellent
N-selectivity.
The
key
to
achieve
this
unprecedented
N–H
rather
than
O–H
insertion
reaction
is
the
use
CpRu(PPh3)2Cl
as
catalyst
sulfoxonium
ylides
alkylation
reagents.
Moreover,
protocol
also
amenable
7-azaindoles
by
slightly
varying
conditions.
Furthermore,
sulfonium
are
suitable
reagents,
providing
selectivity.
Organic Letters,
Год журнала:
2023,
Номер
25(23), С. 4286 - 4291
Опубликована: Июнь 2, 2023
Two
categories
of
tetrasubstituted
phenols
were
prepared
via
the
cycloaddition
reaction
vinyl
sulfoxonnium
ylides
with
cyclopropenones
in
a
switchable
manner.
Copper
carbenoid
was
proposed
as
active
intermediate
process
2,3,4,5-tetrasubstituted
formation,
while
2,3,5,6-tetrasubstituted
generated
direct
[3
+
3]
annulation
under
metal-free
conditions.
Further
synthetic
applications
also
demonstrated.
The Journal of Organic Chemistry,
Год журнала:
2023,
Номер
88(9), С. 5572 - 5585
Опубликована: Апрель 21, 2023
Organoselenium
compounds
are
important
scaffolds
in
pharmaceutical
molecules.
Herein,
we
report
metal-free,
electrochemical,
highly
chemo-
and
regioselective
synthesis
of
gem-diselenides
through
the
coupling
α-keto
sulfoxonium
ylides
with
diselenides.
The
versatility
electrochemical
manifold
enabled
selenylation
ample
scope
broad
functional
group
tolerance,
as
well
setting
stage
for
modification
complex
bioactive
Detailed
mechanistic
studies
revealed
that
key
C-Se
bond
was
constructed
using
n-Bu4NI
an
electrolyte
catalyst
electrosynthetic
protocol.
Finally,
desired
showed
excellent
antimicrobial
activity
against
Candida
albicans,
which
can
be
identified
lead
further
exploration.
Angewandte Chemie International Edition,
Год журнала:
2023,
Номер
62(48)
Опубликована: Окт. 10, 2023
A
novel
and
convenient
approach
that
combines
high-throughput
experimentation
(HTE)
with
machine
learning
(ML)
technologies
to
achieve
the
first
selective
cross-dimerization
of
sulfoxonium
ylides
via
iridium
catalysis
is
presented.
variety
valuable
amide-,
ketone-,
ester-,
N-heterocycle-substituted
unsymmetrical
E-alkenes
are
synthesized
in
good
yields
high
stereoselectivities.
This
mild
method
avoids
use
diazo
compounds
characterized
by
simple
operation,
step-economy,
excellent
chemoselectivity
functional
group
compatibility.
The
combined
experimental
computational
studies
identify
an
amide-sulfoxonium
ylide
as
a
carbene
precursor.
Furthermore,
comprehensive
exploration
reaction
space
also
performed
(600
reactions)
model
for
yield
prediction
has
been
constructed.
