Applications of Organosilanes in Visible Light‐induced Catalytic Asymmetric Reactions
ChemCatChem,
Год журнала:
2024,
Номер
unknown
Опубликована: Март 27, 2024
Abstract
Over
the
past
decades,
visible
light‐mediated
photocatalysis
has
found
a
mainstream
of
applications
in
synthetic
chemistry.
Organosilanes
have
been
proven
to
be
useful
class
electron
donors
generate
highly
active
radical
species
via
photoinduced
single
transfer
oxidation/fragmentation
sequence,
which
may
undergo
follow‐up
coupling
or
addition
process.
This
minireview
highlights
comprehensive
advances
organosilanes
photoredox
catalyzed
asymmetric
organic
synthesis,
with
particular
emphasis
placed
on
reaction
mechanisms.
We
hope
that
this
review
will
inspire
further
design
and
development
new
reactions
such
readily
accessible
reagents.
Язык: Английский
Enantioselective Desymmetrization of Biaryls via Cooperative Photoredox/Brønsted Acid Catalysis and Its Application to the Total Synthesis of Ancistrobrevolines
Journal of the American Chemical Society,
Год журнала:
2025,
Номер
unknown
Опубликована: Апрель 5, 2025
Photoredox
catalysis
has
emerged
as
a
powerful
tool
for
forming
and
breaking
chemical
bonds,
further
taking
hold
with
its
integration
asymmetric
catalysis.
While
the
dual-catalytic
approach
led
to
successful
examples
of
control
stereogenic
centers,
axes
remained
underexplored.
In
this
study,
an
acylimine
intermediate
was
generated
through
photoredox
catalysis,
symmetric
substrate,
2-arylresorcinol,
desymmetrized
aid
chiral
phosphoric
acid
Using
approach,
center
axis
were
successfully
controlled
provide
natural-product-driven
compound.
The
origins
enantioselectivity
diastereoselectivity
investigated
density
functional
theory
study
four
possible
enantiodetermining
transition
states.
Consequently,
first
total
syntheses
ring-contracted
naphthylisoquinoline
alkaloid
ancistrobrevolines
A
B
accomplished
concisely.
This
provides
not
only
novel
methodology
strategy
synthesize
alkaloids
but
also
direction
advance
catalytic
research
synthesis
studies.
Язык: Английский
Photoinduced Enantioselective Transformations via o-Quinodimethane Intermediates
Tetrahedron Chem,
Год журнала:
2025,
Номер
unknown, С. 100131 - 100131
Опубликована: Апрель 1, 2025
Язык: Английский
Enantioselective and Band-Gap Modulation in Photocatalysis of Metal-Free Chiral Carbon Dots
ACS Applied Materials & Interfaces,
Год журнала:
2024,
Номер
16(15), С. 19379 - 19390
Опубликована: Апрель 3, 2024
Photodriven
chiral
catalysis
is
the
combination
of
photocatalysis
and
considered
one
cleanest
most
efficient
methods
for
synthesis
compounds
or
drugs.
Furthermore,
due
to
potential
metal
contamination
associated
with
metal-based
catalysts,
metal-free
photocatalysts
are
ideal
candidates.
In
this
work,
we
demonstrate
that
carbon
dots
(CDs)
exhibit
size-dependent
enantioselective
photocatalytic
activity.
Using
serine
as
raw
material,
CDs
well-defined
structures
average
sizes
2.22,
3.01,
3.70,
4.77,
7.21
nm
were
synthesized
using
electrochemical
method.
These
possess
band
gaps
photoresponsive
catalytic
activity
toward
oxidation
dihydroxyphenylalanine
(DOPA).
Under
light-assisted
conditions,
(L72,
500
μg/mL)
high
selectivity
(selectivity
factor:
2.07)
maintain
a
certain
level
(1.34
μM/min)
even
at
low
temperature
5
°C.
The
arises
from
their
photoelectrons
reducing
O2
generate
O2-,
active
oxygen
species
DOPA
oxidation.
enantioselectivity
attributed
differential
adsorption
capabilities
enantiomers.
This
study
provides
new
approach
designing
enantioselectivity.
Язык: Английский
Modular Assembly of Acridines by Integrating Photo‐Excitation of o‐Alkyl Nitroarenes with Copper‐Promoted Cascade Annulation
Haichao Huang,
Yi‐Fan Jiang,
Wei Yuan
и другие.
Angewandte Chemie International Edition,
Год журнала:
2024,
Номер
unknown
Опубликована: Июль 23, 2024
Abstract
Acridine
frameworks
stand
as
pivotal
architectural
elements
in
pharmaceuticals
and
photocatalytic
applications,
owing
to
their
chemical
adaptability,
biological
activity,
unique
excited‐state
dynamics.
Conventional
synthetic
routes
often
entail
specialized
starting
materials,
anaerobic
or
moisture‐free
conditions,
elaborate
multi‐stage
manipulations
for
incorporating
diverse
functionalities.
Herein,
we
present
a
convergent
approach
integrating
photo‐excitation
of
readily
available
ortho
‐alkyl
nitroarenes
with
copper‐promoted
cascade
annulation.
This
innovative
system
enables
an
aerobic,
one‐pot
reaction
o‐
alkyl
arylboronic
acids,
thereby
streamlining
the
modular
construction
wide
array
acridine
derivatives
various
functional
groups.
encompasses
symmetrical,
unsymmetrical
polysubstituted
varieties,
some
which
are
otherwise
exceptionally
difficult
synthesize.
Furthermore,
it
significantly
improves
production
structurally
varied
acridinium
salts,
featuring
enhanced
photophysical
properties,
high
excited
state
potentials
(
E
*
red
=2.08–3.15
V),
exhibiting
superior
performance
intricate
photoredox
transformations.
Язык: Английский
Modular Assembly of Acridines by Integrating Photo‐Excitation of o‐Alkyl Nitroarenes with Copper‐Promoted Cascade Annulation
Haichao Huang,
Yi‐Fan Jiang,
Wei Yuan
и другие.
Angewandte Chemie,
Год журнала:
2024,
Номер
136(42)
Опубликована: Июль 23, 2024
Abstract
Acridine
frameworks
stand
as
pivotal
architectural
elements
in
pharmaceuticals
and
photocatalytic
applications,
owing
to
their
chemical
adaptability,
biological
activity,
unique
excited‐state
dynamics.
Conventional
synthetic
routes
often
entail
specialized
starting
materials,
anaerobic
or
moisture‐free
conditions,
elaborate
multi‐stage
manipulations
for
incorporating
diverse
functionalities.
Herein,
we
present
a
convergent
approach
integrating
photo‐excitation
of
readily
available
ortho
‐alkyl
nitroarenes
with
copper‐promoted
cascade
annulation.
This
innovative
system
enables
an
aerobic,
one‐pot
reaction
o‐
alkyl
arylboronic
acids,
thereby
streamlining
the
modular
construction
wide
array
acridine
derivatives
various
functional
groups.
encompasses
symmetrical,
unsymmetrical
polysubstituted
varieties,
some
which
are
otherwise
exceptionally
difficult
synthesize.
Furthermore,
it
significantly
improves
production
structurally
varied
acridinium
salts,
featuring
enhanced
photophysical
properties,
high
excited
state
potentials
(
E
*
red
=2.08–3.15
V),
exhibiting
superior
performance
intricate
photoredox
transformations.
Язык: Английский
Proline-based Organocatalyst for the Synthesis of Arylidene Benzofuranone Intermediates Enabling the Construction of Aurone-derived Azadienes
Current Organic Chemistry,
Год журнала:
2024,
Номер
29(2), С. 127 - 134
Опубликована: Авг. 26, 2024
:
Organocatalysis
has
been
recognized
as
a
part
of
chemical
research
for
long
time,
and
it
gained
significant
attention
in
catalysis
recent
decades.
Amine
catalyst
is
substantial
type
organocatalysis,
successively
employed
the
activation
carbonyl
compounds.
This
manuscript
delves
into
exploration
proline-based
organocatalyst
synthesis
arylidene
benzofuranone
intermediates,
critical
step
that
facilitates
subsequent
construction
aurone-derived
azadienes.
In
this
work,
we
successfully
reported
intermediates
through
Aldol
condensation
with
different
aldehydes
enabled
by
proline-derived
organic
catalysts.
To
achieve
strategy,
six
examples
amine
organocatalysts
(A1-A6)
were
evaluated
to
showcase
optimal
transformation.
Moreover,
further
interesting
azadiene
substrates
its
reaction
TsNH2.
Notably,
using
A6
resulted
delivery
product
best
yield
(94%
isolated
yield).
Under
optimized
conditions,
aromatic
heterocyclic
containing
effectively
tolerated
generate
corresponding
which
converted
products
high
excellent
yield.
The
claimed
structures
confirmed
spectral
analysis.
Язык: Английский
Photo‐induced three‐component reaction for the construction of α‐tertiary amino acid derivatives
Chemistry - A European Journal,
Год журнала:
2024,
Номер
30(70)
Опубликована: Сен. 21, 2024
Abstract
The
synthesis
of
α‐tertiary
amino
acids
(ATAAs),
which
are
pivotal
components
in
natural
metabolism
and
pharmaceutical
innovation,
continues
to
attract
significant
research
interest.
Despite
substantial
advancements,
the
pursuit
a
facile,
versatile,
resource‐efficient
methodology
remains
an
area
active
development.
In
this
work,
we
introduce
visible
light‐triggered
three‐component
reaction
involving
readily
available
nitrosoarenes,
N
‐acyl
pyrazoles,
allyl
or
(bromomethyl)benzenes
under
mild
conditions.
This
approach
enables
straightforward
assembly
wide
array
ATAA
derivatives
(42
examples)
commendably
high
yields
(up
89
%).
Mechanistic
investigations
elucidate
that
proceeds
through
dehydration
condensation
between
nitrosoarenes
pyrazoles
generate
ketimine
intermediates.
is
followed
by
light‐driven
halogen
atom
transfer
(XAT)
process
radical
addition,
culminating
formation
desired
products.
showcases
excellent
functional
group
compatibility
late‐stage
derivatization
potential,
offering
new
insights
avenues
for
analogs.
Язык: Английский