Organic Letters,
Journal Year:
2021,
Volume and Issue:
23(23), P. 9292 - 9296
Published: Nov. 19, 2021
Two
new
visible-light-mediated
strategies
are
described
starting
from
aryldiazoacetates.
The
first
approach
describes
their
reaction
with
azides
to
afford
the
corresponding
imines,
and
then
aryldiazoketones
produces
alkyl
2-carboxylate-2,3,3-trisubstituted
β-lactams.
second
sulfoxides
sulfoxonium
ylides,
followed
by
produce
5-alkoxy-2,2,4-trisubstituted
furan-3(2H)-ones.
These
protocols
take
advantage
of
photolysis
aryldiazoacetates
photochemically
promoted
Wolff
rearrangement
aryldiazoketones.
Chemical Communications,
Journal Year:
2023,
Volume and Issue:
59(83), P. 12411 - 12422
Published: Jan. 1, 2023
Sulfoxonium
ylides
are
important
synthetic
precursors
in
various
organic
transformations.
Their
potential
was
well
explored
the
synthesis
of
bioactive
natural
products
and
pharmaceuticals.
Vinyl
sulfoxonium
ylide
is
a
stabilized
containing
an
electron-deficient
alkene
at
ylidic
carbon.
Similar
to
α-keto
ylides,
these
reagents
can
generate
vinyl
carbenes
presence
metals
under
suitable
conditions.
These
be
used
for
transformations
such
as
X-H
(X
=
C,
N,
O,
S)
insertions,
annulations,
rearrangement
reactions.
Due
dipole
structure
ylide,
it
undergo
electrophilic
addition
with
electrophiles
α-position.
synthons
aromatic
heteroaromatic
compound
syntheses.
Moreover,
their
stability
convenient
handling
make
them
replacements
thermally
less
stable
diazo
compounds.
Herein,
we
provide
overview
early
efforts
this
area,
particular
emphasis
on
our
own
recent
development
ylide-mediated
absence
metal
catalysis,
also
give
personal
perspectives
challenges
future
scope
improving
application
ylides.
Angewandte Chemie International Edition,
Journal Year:
2024,
Volume and Issue:
63(24)
Published: April 8, 2024
We
here
reported
a
highly
stereoselective
method
for
the
synthesis
of
polysubstituted
conjugated
dienes
from
α-aryl
α-diazo
alkynyl
ketones
and
pyrazole-substituted
unsymmetric
aminals
under
mild
conditions,
which
was
promoted
by
photo-irridation
involved
with
1,6-dipolar
intermediate
quadruple
sigmatropic
rearrangements,
successfully
developed.
In
this
transformation,
cleavage
four
bonds
recombination
five
were
implemented
in
one
operational
step.
This
protocol
provided
modular
tool
constructing
amines,
pyrazoles
α-alkynyl-α-diazoketones
one-pot
manner.
The
results
mechanistic
investigation
indicated
that
plausible
reaction
path
underwent
1,6-sigmatropic
rearrangement
instead
1,5-sigmatropic
rearrangement.
The Journal of Organic Chemistry,
Journal Year:
2020,
Volume and Issue:
86(1), P. 1012 - 1022
Published: Dec. 10, 2020
A
blue-light-emitting
diode
(LED)
promoted
coupling
of
aryl
diazoacetates
with
sulfur
ylides
is
described.
This
protocol
features
mild
conditions,
good
functional
group
tolerance,
and
broad
substrate
scope
for
both
ylides.
Under
optimal
reaction
a
wide
range
trisubstituted
olefins
obtained
in
moderate
to
yield,
which
can
be
further
transferred
other
biologically
important
heterocycles
after
two-step
simple
operation.
Nature Communications,
Journal Year:
2021,
Volume and Issue:
12(1)
Published: Dec. 15, 2021
Abstract
Tetraarylethylenes
exhibit
intriguing
photophysical
properties
and
sulfur
atom
frequently
play
a
vital
role
in
organic
photoelectric
materials
biologically
active
compounds.
Tetrasubstituted
vinyl
sulfides,
which
include
both
tetrasubstituted
alkenes
motifs,
might
be
suitable
skeleton
for
the
discovery
of
new
material
molecules
drug
with
unique
functions
properties.
However,
how
to
modular
synthesis
these
kinds
compounds
is
still
challenging.
Herein,
chemo-
stereo-selective
Rh(II)-catalyzed
[1,4]-acyl
rearrangements
α-diazo
carbonyl
thioesters
has
been
developed,
providing
strategy
library
63
sulfides.
In
this
transformation,
yield
up
95%
turnover
number
3650.
The
mechanism
reaction
investigated
by
combining
experiments
density
functional
theory
calculation.
Moreover,
“aggregation-induced
emission”
effect
sulfides
were
also
investigated,
useful
material,
biological
imaging
chemicalnsing
via
structural
modification.
Organic Letters,
Journal Year:
2021,
Volume and Issue:
23(23), P. 9292 - 9296
Published: Nov. 19, 2021
Two
new
visible-light-mediated
strategies
are
described
starting
from
aryldiazoacetates.
The
first
approach
describes
their
reaction
with
azides
to
afford
the
corresponding
imines,
and
then
aryldiazoketones
produces
alkyl
2-carboxylate-2,3,3-trisubstituted
β-lactams.
second
sulfoxides
sulfoxonium
ylides,
followed
by
produce
5-alkoxy-2,2,4-trisubstituted
furan-3(2H)-ones.
These
protocols
take
advantage
of
photolysis
aryldiazoacetates
photochemically
promoted
Wolff
rearrangement
aryldiazoketones.
