Advanced Synthesis & Catalysis,
Journal Year:
2023,
Volume and Issue:
365(24), P. 4672 - 4676
Published: Nov. 10, 2023
Abstract
2‐Iminothiazolidin‐4‐one,
5‐ethylidenethiazolidin‐4‐one,
and
thiazolidine‐4‐thione
are
all
medicinally
relevant
structures.
In
this
work,
a
NaSO
2
CF
3
‐promoted
[2+2+1]
cascade
annulation
reaction
of
‐imidoyl
sulfoxonium
ylides
isothiocyanates
was
reported
to
synthesize
variety
decorated
thiazolidine‐4‐thiones
in
35–91%
yields
with
exclusive
stereoselectivity.
The
gram‐scale
further
chemoselective
S
‐alkylations
demonstrated
the
synthetic
utilities
transformation.
Chemical Reviews,
Journal Year:
2022,
Volume and Issue:
122(15), P. 12544 - 12747
Published: July 17, 2022
1,1,1,3,3,3-Hexafluoroisopropanol
(HFIP)
is
a
polar,
strongly
hydrogen
bond-donating
solvent
that
has
found
numerous
uses
in
organic
synthesis
due
to
its
ability
stabilize
ionic
species,
transfer
protons,
and
engage
range
of
other
intermolecular
interactions.
The
use
this
exponentially
increased
the
past
decade
become
choice
some
areas,
such
as
C–H
functionalization
chemistry.
In
review,
following
brief
history
HFIP
an
overview
physical
properties,
literature
examples
reactions
using
or
additive
are
presented,
emphasizing
effect
each
reaction.
Organic Chemistry Frontiers,
Journal Year:
2022,
Volume and Issue:
9(16), P. 4388 - 4393
Published: Jan. 1, 2022
The
synthesis
of
3-trifluoromethylisoquinolinones
by
a
ruthenium(
ii
)-catalyzed
C–H
activation/annulation
reaction
benzoic
acids
and
CF
3
-imidoyl
sulfoxonium
ylides
has
been
achieved.
Asian Journal of Organic Chemistry,
Journal Year:
2022,
Volume and Issue:
11(4)
Published: March 23, 2022
Abstract
In
recent
years,
the
transition‐metal‐catalyzed
functionalization
reactions
of
sulfoxonium
ylides
have
been
explored
extensively
because
their
usefulness
as
carbene‐transfer
agents,
since
they
can
produce
metal
carbenes
through
catalysis.
Moreover,
are
safer
and
advantages
simple
handling
good
stability
over
other
counterparts
like
diazo‐compounds.
This
review
article
attempts
to
highlight
advances
in
metal‐catalyzed
C−H
ylides.
The Journal of Organic Chemistry,
Journal Year:
2021,
Volume and Issue:
87(2), P. 1124 - 1132
Published: Dec. 29, 2021
An
efficient
and
practical
strategy
was
developed
to
synthesize
1,3,4-triaryl-6-trifluoromethylpyridones
from
CF3-imidoyl
sulfoxonium
ylides
cyclopropenones
in
good
excellent
yields.
This
stepwise
[3
+
3]
annulation
reaction
carried
out
under
transition-metal-,
additive-,
solvent-free
conditions,
generating
1
equiv
of
dimethyl
sulfoxide
as
byproduct
tolerating
a
series
functional
groups.
Organic Letters,
Journal Year:
2022,
Volume and Issue:
24(43), P. 8062 - 8066
Published: Oct. 24, 2022
An
efficient
base,
additive
and
metal-free
synthetic
methods
for
α-ketothioamide
α-ketoamide
derivatives
from
readily
available
sulfoxonium
ylides
have
been
described.
Sulfoxonium
with
primary
or
secondary
amines
afforded
α-ketothioamides
in
the
presence
of
elemental
sulfur,
whereas
α-ketoamides
were
produced
when
I2
TBHP
present.
The
reaction
proceeded
well
at
room
temperature
generated
corresponding
molecules
good
to
excellent
yields.
can
be
scaled-up
tolerated
by
a
range
functional
groups
simple
operational
procedures.
Organic Letters,
Journal Year:
2021,
Volume and Issue:
23(19), P. 7407 - 7411
Published: Sept. 20, 2021
A
lithium-bromide-promoted
nucleophilic
substitution/annulation
cascade
reaction
between
CF3-imidoyl
sulfoxonium
ylides
and
1,3-dicarbonyl
compounds
has
been
established,
the
corresponding
1,2,3-trisubstituted
5-trifluoromethylpyrroles
have
obtained
in
27–78%
yield.
This
features
a
broad
substrate
scope
generates
dimethyl
sulfoxide
H2O
as
byproducts.
Chemical Communications,
Journal Year:
2020,
Volume and Issue:
56(49), P. 6688 - 6691
Published: Jan. 1, 2020
A
rhodium(iii)-catalyzed
ortho-C-H
functionalization
of
sulfoxonium
ylides
followed
by
intramolecular
annulation
reactions
with
quinones
was
described,
where
the
carbonyl
in
served
as
a
chelation
group.
This
protocol
leads
to
efficient
formation
2-hydroxy-6H-benzo[c]chromen-6-one
derivatives,
proceeding
cleavage
C(O)-S
bond
ylides.
featured
high
chemo-selectivity
and
functional
group
tolerance,
acted
aroyl
sources.
Chinese Journal of Chemistry,
Journal Year:
2021,
Volume and Issue:
39(9), P. 2489 - 2494
Published: May 9, 2021
Main
observation
and
conclusion
Divergent
synthesis
of
useful
skeletons
has
been
realized
via
rhodium(III)‐catalyzed
C—H
activation
iminopyridinium
ylides
coupling
with
various
unsaturated
reagents.
Isocoumarins
isoquinolones
were
obtained
cleavage
the
C—N
or
N—N
bond
in
ylidic
directing
group,
while
fluorinated
alkenes
delivered
group
intact.
The
reactions
occurred
wide
substrate
scopes
good
efficiency
under
redox‐neutral
air‐tolerant
conditions.
Representative
products
exhibit
solid‐state
fluorescent
property
bioactivity
inhibition
toward
human
cancer
cells.
