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.
Angewandte Chemie International Edition,
Journal Year:
2019,
Volume and Issue:
58(36), P. 12491 - 12496
Published: July 11, 2019
An
enantioselective
sulfenylation/semipinacol
rearrangement
of
1,1-disubstituted
and
trisubstituted
allylic
alcohols
was
accomplished
with
a
chiral
Lewis
base
Brønsted
acid
as
cocatalysts,
generating
various
β-arylthio
ketones
bearing
an
all-carbon
quaternary
center
in
moderate
to
excellent
yields
enantioselectivities.
These
arylthio
ketone
products
are
common
intermediates
many
applications,
for
example,
the
design
new
catalysts/ligands
total
synthesis
natural
products.
Computational
studies
(DFT
calculations)
were
carried
out
explain
enantioselectivity
role
acid.
Additionally,
synthetic
utility
this
method
exemplified
by
(-)-herbertene
one-pot
sulfoxide
sulfone.
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 Chemical Record,
Journal Year:
2020,
Volume and Issue:
20(11), P. 1269 - 1296
Published: Sept. 15, 2020
Abstract
Chiral
thioethers
is
an
important
class
of
organosulfur
molecules
with
extensive
applications,
especially
in
the
field
medicine
and
organic
synthesis.
This
review
discusses
recent
progress
synthesis
enantioenriched
chiral
hopes
to
be
helpful
for
related
research
future.
It
summarized
from
compounds‐participating
reaction
types,
including
nucleophilic
substitution,
cross
coupling,
sulfa‐Michael
addition,
sulfenylation,
asymmetric
allylic
reaction,
Doyle‐Kirmse
Pummerer‐type
rearrangement,
Smiles
[2,3]
Stevens
Sommelet‐Hauser
rearrangement.
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.
