Merging Photoexcited Nitroarenes with Lewis Acid Catalysis for the Anti-Markovnikov Oxidation of Alkenes
Organic Letters,
Год журнала:
2025,
Номер
unknown
Опубликована: Фев. 20, 2025
Herein
we
describe
the
oxidation
of
alkenes
to
carbonyls
and
acetonides
via
interplay
photoexcited
nitroarenes
Lewis
acid
catalysis.
A
wide
range
were
oxidized
aldehyde
ketone
products
with
anti-Markovnikov
selectivity
when
acetone
was
employed
as
a
co-solvent.
Mechanistic
studies
support
that
coordination
1,3,2-dioxazolidine
intermediate
results
in
1,2-shift
generate
carbonyl
derivatives
nucleophilic
substitution
pathway
for
formation
acetonides.
Язык: Английский
Transformative Reactions in Nitroarene Chemistry: Advances in C–N Bond Cleavage, Skeletal Editing, and N–O Bond Utilization
Organic & Biomolecular Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Янв. 1, 2025
This
review
aims
to
provide
a
comprehensive
overview
of
the
expanding
utility
nitroarenes
and
their
potential
for
future
applications
in
synthetic
organic
chemistry.
Язык: Английский
Photoinduced Reductive [4 + 2] Cycloaddition of Nitroarenes
Organic Letters,
Год журнала:
2025,
Номер
unknown
Опубликована: Фев. 26, 2025
Direct
C-N
bond
formation
from
nitroarenes
is
a
valuable
synthetic
tool
for
quick
access
to
aniline
derivatives.
Transformation
via
nitroso
intermediates
could
be
useful
due
their
unique
properties,
but
the
generation
of
nitrosoarenes
in
situ
challenging
tendency
various
side
reactions.
Herein
we
report
photoinduced
reductive
[4
+
2]
cycloaddition
nitroarenes.
The
method
begins
with
reduction
give
by
hydrogen
atom
abstraction
(HAA).
generated
undergo
Diels-Alder
(NDA)
reaction.
key
success
use
N-heterocyclic
carbene
(NHC)
borane,
which
promotes
efficient
HAA,
enabling
NDA
reaction
proceed
without
need
transition
metals,
strong
bases,
or
elevated
temperatures.
developed
conditions
allow
high
functional
group
tolerance,
late-stage
functionalization
and
further
derivatization
biologically
active
compounds.
Язык: Английский
Visible Light-Photoinduced and Cu-Catalyzed Reduction of Nitrobenzenes into Anilines
ACS Catalysis,
Год журнала:
2025,
Номер
unknown, С. 4726 - 4738
Опубликована: Март 6, 2025
Язык: Английский
Nitroarenes as the Visible-Light-Responsive Photocatalysts for the Multimode Aerobic Oxidation
ACS Catalysis,
Год журнала:
2025,
Номер
unknown, С. 8865 - 8875
Опубликована: Май 11, 2025
Язык: Английский
Photoexcited nitroarene-enabled carbon chain-elongated oxidation of alkenes via tandem oxidative cleavage and dipolar cycloaddition
Nature Communications,
Год журнала:
2025,
Номер
16(1)
Опубликована: Май 15, 2025
Oxidation
of
alkenes
with
O3
and
photoexcited
nitroarenes
represents
one
the
most
attractive
organic
chemical
transformations
for
synthesis
oxygen-enriched
molecules.
However,
known
achievements
are
mainly
limited
to
carbon
chain-shortened
oxidation
chain-retained
alkenes.
Given
that
constructing
higher
molecular
complexity
is
core
goal
modern
synthesis,
development
chain-elongated
would
be
in
high
demand
but
still
remains
an
elusive
challenge
so
far.
Herein,
we
report
a
nitroarene-enabled
highly
regioselective
via
tandem
oxidative
cleavage
dipolar
cycloaddition,
providing
broad
range
synthetically-useful
isoxazolidines
up
92%
yield
from
readily
available
enol
ethers
or
styrene
derivatives
under
simple
mild
conditions.
Язык: Английский