1,3-diene-based AIEgens: Stereoselective synthesis and applications
Xiao‐Mei Nong,
Ao Gu,
Shuyang Zhai
и другие.
iScience,
Год журнала:
2024,
Номер
27(3), С. 109223 - 109223
Опубликована: Фев. 15, 2024
SummaryIn
recent
years,
significant
advancements
have
been
made
in
the
synthesis
and
application
of
1,3-dienes.
This
specific
structural
motif
has
garnered
attention
from
researchers
materials
science
biology
due
to
its
unique
aggregation-induced
emission
(AIE)
properties
extensive
conjugation
systems.
The
luminescent
characteristics
these
compounds
are
notably
influenced
by
geometry
two
double
bonds.
Therefore,
it
is
essential
consolidate
stereoselective
synthetic
strategies
for
comprehensive
review
seeks
elucidate
diverse
techniques
employed
attain
stereo-control
1,3-diene-based
AIE
luminogens
(AIEgens).
Particular
emphasis
placed
on
comprehending
determinants
stereoselectivity
exploring
array
substrates
amenable
methods.
Furthermore,
underscores
exhibited
their
utility
organic
light-emitting
diodes
(OLEDs),
stimuli-responsive
materials,
sensors,
bioimaging,
photodynamic
therapy
(PDT).Graphical
abstract
Язык: Английский
Regio‐ and Stereo‐Selective Isomerization of Borylated 1,3‐Dienes Enabled by Selective Energy Transfer Catalysis
Byeongseok Kweon,
Lukas Blank,
Julia Soika
и другие.
Angewandte Chemie International Edition,
Год журнала:
2024,
Номер
63(22)
Опубликована: Март 28, 2024
Abstract
Configurationally‐defined
dienes
are
pervasive
across
the
bioactive
natural
product
spectrum,
where
they
typically
manifest
themselves
as
sorbic
acid‐based
fragments.
These
C
5
motifs
reflect
biosynthesis
algorithms
that
facilitate
their
construction.
To
complement
established
biosynthetic
paradigms,
a
chemical
platform
to
construction
of
stereochemically
defined,
functionalizable
by
light‐enabled
isomerization
has
been
devised.
Enabled
selective
energy
transfer
catalysis,
variety
substituted
β‐boryl
acid
derivatives
can
be
isomerized
in
regio‐
and
stereo‐selective
manner
(up
97
:
3).
Directionality
is
guided
stabilizing
n
O
→p
B
interaction
product:
this
constitutes
formal
anti
‐hydroboration
starting
alkyne.
This
operationally
simple
reaction
employs
low
catalyst
loadings
(1
mol
%)
complete
1
h.
X‐ray
analysis
supports
hypothesis
leads
chromophore
bifurcation:
provides
structural
foundation
for
transfer.
Язык: Английский
Photoinduced Copper-Catalyzed 1,2-Difunctionalization of 1,3-Dienes with Aryl Diselenides
The Journal of Organic Chemistry,
Год журнала:
2023,
Номер
88(22), С. 15969 - 15974
Опубликована: Окт. 30, 2023
Described
herein
is
a
photoinduced
copper-catalyzed
1,2-difunctionalization
of
1,3-dienes.
The
selenium
atom
radical
was
generated
by
the
visible
light
irradiation
diselenides,
triggering
addition
with
1,3-dienes
to
form
allyl
intermediate.
Subsequent
rapid
Z/E
isomerization
allowed
for
thermodynamically
favorable
intermediate
formation
and
enabled
copper
catalyzed
stereoselective
functionalization
various
nucleophiles.
Язык: Английский
A palladium catalyzed stereo-convergent aminocarbonylation of 1,3-dienes with nitroarenes: synthesis of (E,E)-dienamides
Jin‐Liang Lu,
Yun Chan Kang,
Zhi Zhang
и другие.
Organic Chemistry Frontiers,
Год журнала:
2022,
Номер
9(23), С. 6505 - 6512
Опубликована: Янв. 1, 2022
A
palladium
catalyzed
stereo-convergent
aminocarbonylation
of
1,3-dienes
with
nitroarenes
has
been
developed.
The
reaction
mixtrues
E
/
Z
isomers
reacted
and
produced
(
,
)-dienamides
high
stereoselectivities.
Язык: Английский
Cobalt-Catalyzed Asymmetric Hydrosilylation of α-Oxygenated Ketones
Organic Letters,
Год журнала:
2023,
Номер
25(13), С. 2184 - 2189
Опубликована: Март 24, 2023
An
asymmetric
hydrosilylation
of
α-oxygenated
ketones
was
developed
under
the
catalysis
Co(OAc)2
in
combination
with
a
chiral
phosphine-amido-oxazoline
(PAO)
ligand,
providing
mild,
efficient,
and
enantioselective
access
to
variety
synthetically
useful
1,2-diol
derivatives.
This
protocol
can
be
carried
out
at
gram
scale
catalyst
loading
1
mol
%,
its
synthetic
utility
demonstrated
by
efficient
conversion
optically
enriched
products
into
α-hydroxy
acid,
1,3-dioxolan-2-one,
ethylene
oxide,
1,2,3-1H-triazole.
Язык: Английский
Regio‐ and Stereo‐Selective Isomerization of Borylated 1,3‐Dienes Enabled by Selective Energy Transfer Catalysis
Byeongseok Kweon,
Lukas Blank,
Julia Soika
и другие.
Angewandte Chemie,
Год журнала:
2024,
Номер
136(22)
Опубликована: Март 28, 2024
Abstract
Configurationally‐defined
dienes
are
pervasive
across
the
bioactive
natural
product
spectrum,
where
they
typically
manifest
themselves
as
sorbic
acid‐based
fragments.
These
C
5
motifs
reflect
biosynthesis
algorithms
that
facilitate
their
construction.
To
complement
established
biosynthetic
paradigms,
a
chemical
platform
to
construction
of
stereochemically
defined,
functionalizable
by
light‐enabled
isomerization
has
been
devised.
Enabled
selective
energy
transfer
catalysis,
variety
substituted
β‐boryl
acid
derivatives
can
be
isomerized
in
regio‐
and
stereo‐selective
manner
(up
97
:
3).
Directionality
is
guided
stabilizing
n
O
→p
B
interaction
product:
this
constitutes
formal
anti
‐hydroboration
starting
alkyne.
This
operationally
simple
reaction
employs
low
catalyst
loadings
(1
mol
%)
complete
1
h.
X‐ray
analysis
supports
hypothesis
leads
chromophore
bifurcation:
provides
structural
foundation
for
transfer.
Язык: Английский
Ligand-Controlled Cobalt-Catalyzed Regiodivergent and Stereoselective Ring-Opening Isomerization of Vinyl Cyclopropanes
Organic Letters,
Год журнала:
2024,
Номер
26(23), С. 5004 - 5009
Опубликована: Июнь 3, 2024
A
ligand-controlled
regiodivergent
and
stereoselective
ring-opening
isomerization
of
vinylcyclopropane
was
developed
with
cobalt
catalysis.
Employing
the
commercially
available
Xantphos
ligand,
reactions
afforded
exclusively
linear-type
1,3-dienes
as
products.
Interestingly,
when
switching
ligand
to
an
amido-diphosphine
(PNP),
branched-type
were
obtained
high
regioselectivity
stereoselectivity.
Preliminary
mechanistic
investigations
suggested
that
a
π-allyl
metal
metal-hydride
species
are
involved
key
intermediates
in
two
transformations,
respectively.
Язык: Английский
Nickel-Catalyzed Stereoconvergent C(sp2)–F Alkenylation of Monofluoroalkenes
Organic Letters,
Год журнала:
2024,
Номер
26(40), С. 8521 - 8526
Опубликована: Сен. 27, 2024
The
stereoconvergent
synthesis
of
a
single
stereoisomer
from
Язык: Английский
Ligand-controlled cobalt-catalyzed isomerization and reductive C–O bond cleavage of allylic ethers
Organic Chemistry Frontiers,
Год журнала:
2023,
Номер
10(18), С. 4643 - 4648
Опубликована: Янв. 1, 2023
Cobalt-catalyzed
isomerization
and
reductive
cleavage
of
allylic
ethers
are
described,
which
controlled
by
the
selection
ligand.
Язык: Английский