Asian Journal of Organic Chemistry,
Год журнала:
2024,
Номер
unknown
Опубликована: Окт. 24, 2024
Abstract
In
the
present
study,
mechanism,
origin
of
stereoselectivity,
and
role
catalyst
organocatalytic
homologation
reaction
between
phenyl
boronate
trifluoromethyl
diazomethane
have
been
theoretically
investigated
using
density
functional
theory
(DFT)
method.
Based
on
calculations,
in
situ
generated
ethanol
plays
significant
triggering
reaction.
Moreover,
[1,2]‐boron
migration
process
is
stereoselectivity‐determining
step,
with
S
‐configured
isomer
being
predominantly.
addition,
NCI
analysis
performed
to
disclose
stereoselectivity.
Nature Communications,
Год журнала:
2025,
Номер
16(1)
Опубликована: Янв. 7, 2025
3-Amino
boron
dipyrromethenes
(BODIPYs)
are
a
versatile
class
of
fluorophores
widely
utilized
in
live
cell
imaging,
photodynamic
therapy,
and
fluorescent
materials
science.
Despite
the
growing
demand
for
optically
active
BODIPYs,
synthesis
chiral
3-amino-BODIPYs,
particularly
catalytic
asymmetric
version,
remains
challenge.
Herein,
we
report
boron-stereogenic
3-amino-BODIPYs
via
palladium-catalyzed
desymmetric
C–N
cross-coupling
prochiral
3,5-dihalogen-BODIPYs.
This
approach
features
broad
substrate
scope,
excellent
functional
group
tolerance,
high
efficiency,
remarkable
enantioselectivities,
under
mild
reaction
conditions.
Further
stereospecific
formation
3,5-diamino-BODIPYs,
along
with
an
investigation
into
photophysical
properties
resulting
optical
BODIPYs
also
explored.
protocol
not
only
enriches
chemical
space
chiroptical
BODIPY
dyes
but
contributes
to
realm
chemistry.
(BODIPYs),
which
useful
science,
authors
first
cross-couplings.
Nature Communications,
Год журнала:
2025,
Номер
16(1)
Опубликована: Март 19, 2025
Tetracoordinate
boron-based
fluorescent
materials
have
shown
extensively
applications
in
chemistry,
biology
and
science
owing
to
their
unique
optoelectronic
properties.
However,
constructing
chiral
boron-stereogenic
fluorophores
through
practical
universal
strategies
remains
rare
challenging.
Herein,
as
a
proof
of
concept,
we
report
an
enantioselective
postfunctionalization
boron
dipyrromethene
dyes
(BODIPYs),
acess
BODIPYs
moderate
good
yields
with
commendable
enantioselectivity.
Chiral
attracted
increasing
attention
not
only
distinctively
photophysical
properties
circularly
polarized
luminescence
(CPL)
materials,
but
also
diversely
structural
modification.
In
this·work,
present
phase-transfer-catalyst
enabled
C–N
coupling
reaction
diverse
nucleophiles.
This
method
serves
SNAr
(nucleophilic
aromatic
substitution
reaction)
route
achieve
series
amido/amino
well
demonstrates
promising
CD
and·CPL·activities,
excellent
biocompatibility,
high
specificities,
showing
potential
imaging
agents.
Constructing
Here,
the
authors
European Journal of Organic Chemistry,
Год журнала:
2024,
Номер
27(14)
Опубликована: Март 7, 2024
Abstract
Boron‐based
enantiomerism
is
fragile
due
to
the
inherent
tendency
of
a
dissociation
ligand
from
tetra‐coordinate
chiral
boron
complexes
under
formation
achiral
tri‐coordinate
species.
This
review
will
present
different
approaches
in
overcoming
racemization
boron‐stereogenic
compounds.
When
embedded
an
environment
ligands
or
substituents,
configurationally
stable
stereogenic
centers
can
form
diastereoselective
manner.
Compounds
incorporating
as
exclusive
center
are
obtained
by
resolution
racemic
mixtures.
The
recently
developed
–
much
more
efficient
methods
catalytic,
enantioselective
creation
compounds
highlighted
this
review.
Finally
chiroptical
properties
enantiomerically
pure
that
makes
them
promising
materials
devices
addressed.
Analytical Chemistry,
Год журнала:
2024,
Номер
96(5), С. 2152 - 2157
Опубликована: Янв. 27, 2024
Sensing
materials
innovation
plays
a
crucial
role
in
the
development
of
high-performance
film-based
fluorescent
sensors
(FFSs).
In
our
current
study,
we
present
innovative
fabrication
four
nanofilms
via
interfacially
confined
dynamic
reaction
specially
designed
building
block,
new
boron-coordinated
compound
(NI-CHO),
with
chosen
one,
benzene-1,3,5-tricarbohydrazide
(BTH).
The
as
prepared
are
robust,
uniform,
flexible,
and
thickness
tunable,
at
least
from
40
to
1500
nm.
fabricated
FFSs
based
on
Film
3,
one
nanofilms,
shows
highly
selective
fully
reversible
response
NH
Chinese Journal of Chemistry,
Год журнала:
2024,
Номер
42(19), С. 2401 - 2411
Опубликована: Май 27, 2024
Comprehensive
Summary
The
21
st
century
has
witnessed
a
continuous
evolution
in
the
development
of
boron‐stereogenic
chemistry.
Since
1990s,
various
innovations
for
synthesis
tetracoordinate
compounds,
which
exhibited
great
potential
applications,
have
been
demonstrated
by
synthetic
chemists.
This
paper
reviews
significant
progress
and
recent
advances
towards
assembly
enantioenriched
hopes
to
shed
light
on
new
perspectives
inspire
further
research
this
emerging
field.
JACS Au,
Год журнала:
2025,
Номер
5(4), С. 1965 - 1973
Опубликована: Апрель 2, 2025
The
precise
construction
of
boron
stereogenic
centers
represents
a
significant,
yet
challenging
frontier
in
asymmetric
catalysis,
garnering
growing
attention
recent
years.
However,
feasible
catalysis
has
primarily
been
limited
to
transition-metal-catalyzed
desymmetrization
pro-chiral
BODIPY
molecules,
while
enantioselective
synthesis
via
organocatalysis
remains
unexplored.
Herein,
we
achieve
an
organocatalyzed
C-N
bond-forming
SNAr
reaction
3,5-dihalogen
BODIPYs
phase-transfer
enabling
the
efficient
broad
range
boron-stereogenic
with
excellent
enantioselectivities
(>40
examples,
up
99%
ee).
significance
and
potential
this
catalytic
approach
are
further
underscored
by
versatile
applications
enantioenriched
3-amide
synthesis,
optical
activity
regulation,
bioimaging,
sensing,
promoting
development
fluorophores.
The
development
of
chiral
BODIPYs
attracts
remarkable
interest
due
to
their
unique
properties,
structural
diversity,
and
good
photochemical
stability,
whereas
achieving
the
construction
maintains
scarce.
Herein,
we
present
an
enantioselective
synthesis
axially
through
Suzuki-Miyaura
coupling.
newly
synthesized
coassembly
showed
desirable
photophysical
including
high
fluorescence
quantum
yields
intense
CPL,
both
in
solution
solid
state.
