A
cascade
reaction
of
α-aryl
vinyl
and
propargyl
sulfonium
salts
with
C-nucleophiles
afforded
functionalized
thioethers
via
Michael
addition
followed
by
[2,3]-sigmatropic
rearrangement.
Organic Letters,
Journal Year:
2020,
Volume and Issue:
22(15), P. 5941 - 5946
Published: July 29, 2020
Solvent-controlled
divergent
domino
annulation
reactions
between
2-hydroxy-2-methylchromene
derivatives
and
prop-2-ynylsulfonium
salts
have
been
developed.
Specifically,
a
sequential
[4
+
2]
reaction
occurred
in
1,2-dichloroethane
affording
sulfur-containing
benzo-fused
dioxabicyclo[3.3.1]nonanes.
In
contrast,
by
changing
the
solvent
to
toluene,
course
switched
1]
afford
dihydrofuro[2,3-c]chromenes.
It
is
noteworthy
that
salt
participates
transformation
with
its
γ-carbon
atom
for
first
time.
Synthesis,
Journal Year:
2021,
Volume and Issue:
54(01), P. 67 - 78
Published: Aug. 4, 2021
Abstract
Allyl
and
propargyl
sulfonium
salts
are
readily
available
reagents
that
have
recently
emerged
as
versatile
building
blocks
for
the
assembly
of
cyclic
skeletons.
As
an
alternative
to
classical
salts,
allyl
can
be
converted
into
corresponding
vinyl
sulfur
ylide
or
allenic
salt
intermediates
contain
diverse
nucleophilic
electrophilic
reactive
positions,
thereby
enabling
a
great
variety
annulation
reactions.
In
this
short
review,
we
provide
comprehensive
overview
recent
developments
in
growing
field
by
summarizing
reactions
involving
salts.
1
Introduction
2
Annulations
with
Sulfonium
Salts
3
Propargyl
4
Conclusion
Organic & Biomolecular Chemistry,
Journal Year:
2023,
Volume and Issue:
21(36), P. 7311 - 7315
Published: Jan. 1, 2023
We
report
a
tBuOK-promoted
synthesis
of
1,3-dihydro-2H-pyrrol-2-one
and
4-methylenepyrrolidin-2-one
systems
via
Conia-ene
like
intramolecular
cyclization.
The
method
features
extremely
short
reaction
times
(5
min)
mild
conditions
(rt),
enabling
the
trapping
propargyl
unit
by
an
amide
enolate.
An
intriguing
anionic
chain
mechanism
is
at
work,
which
can
trigger
isomerization
exo-alkene
giving
access
to
otherwise
elusive
endo-product.
Chemistry - A European Journal,
Journal Year:
2020,
Volume and Issue:
27(2), P. 585 - 588
Published: Sept. 1, 2020
Abstract
A
formal
reductive
[3+2]
annulation
of
4,4,4‐trifluorocrotonate
and
α‐iminoketones
was
developed
under
Brønsted
base
catalysis.
single
phosphazene
efficiently
catalyzes
the
one‐pot
tandem
reaction
involving
two
mechanistically
different
elementary
processes,
namely
chemoselective
reduction
an
imine
moiety
with
thiols
as
reductant
subsequent
intermolecular
Michael
addition
enolate
α‐aminoketones
concomitant
lactam
formation.
This
operationally
simple
method
provides
β‐trifluoromethyl‐substituted
γ‐lactams
a
tetrasubstituted
carbon
diastereomer.
ACS Sustainable Chemistry & Engineering,
Journal Year:
2022,
Volume and Issue:
10(46), P. 15344 - 15349
Published: Nov. 4, 2022
The
first
propargyl
sulfur
ylides
involving
a
cyclopropanation
reaction
between
sulfonium
salts
and
acrylonitrile
derivatives
is
presented.
Propargyl
act
as
unusual
alkyne-group-delivering
reagents
in
this
transformation.
Various
alkynylcyclopropanes
bearing
three
contiguous
stereocenters
were
constructed
moderate
to
high
yields
with
excellent
diastereoselectivity
under
mild
conditions.
Organic & Biomolecular Chemistry,
Journal Year:
2020,
Volume and Issue:
18(43), P. 8867 - 8875
Published: Jan. 1, 2020
We
have
synthesized
a
series
of
pyrrolo[2,1-a]quinolines,
pyrrolo[2,1-a]phthalazines,
and
indolizines
via
sequential
[3
+
2]
annulation
prop-2-ynylsulfonium
salt
N-ylides.
Journal of Heterocyclic Chemistry,
Journal Year:
2023,
Volume and Issue:
60(11), P. 1938 - 1944
Published: Aug. 21, 2023
Abstract
We
have
developed
a
diversity‐oriented,
substrate‐controlled,
chemoselective
synthetic
method
for
variety
of
structurally
diverse
1‐sulfonylquinazoline‐2,4(1H,3H)‐diones
and
2‐sulfonamidobenzonitriles.
This
substrate‐controlled
synthesis
is
accomplished
through
the
condensation
reaction
2‐(sulfonamido)benzamides
with
or
without
an
N‐methyl
group
on
amides.
The
reactions
are
fulfilled
within
half
hour
at
room
temperature
solid
triphosgene
as
convenient
condensing
agent
pyridine
acid
acceptor.
protocol
features
easily
available
starting
materials,
mild
conditions,
easy
experimental
operation,
moderate
to
excellent
yields
products.
