ACS Omega,
Journal Year:
2024,
Volume and Issue:
9(50), P. 49825 - 49831
Published: Dec. 2, 2024
The
electrochemically
induced
reaction
between
alkenes,
bearing
an
allylic
hydrogen
atom,
and
N-hydroxyphthalimide
was
investigated.
Cross-dehydrogenative
C–O
coupling
with
phthalimide-N-oxyl
radical,
derived
from
N-hydroxyphthalimide,
occurs
instead
of
oxidation
the
site,
formation
a
carbonyl
group
or
functionalization
double
C═C
bond.
discovered
transformation
proceeds
in
undivided
electrochemical
cell
equipped
carbon
felt
anode
platinum
cathode.
Coupling
products
were
obtained
yields
up
to
79%.
developed
process
is
based
on
abstraction
atom
position
for
while
bond
remains
unreacted.
method
exploits
ability
radical
abstract
atoms
following
interception
intermediate
C-centered
radical.
The Journal of Organic Chemistry,
Journal Year:
2025,
Volume and Issue:
90(4), P. 1683 - 1696
Published: Jan. 17, 2025
In
the
vanguard
of
sustainable
chemistry,
pursuit
efficient
pathways
for
synthesis
alkyl
bicyclo[1.1.1]pentane-heteroaryls
has
captured
attention
scientific
vanguard.
We
herein
report
a
groundbreaking
and
eco-conscious
multicomponent
coupling
reaction
that
paves
way
alkylation
heteroarylation
[1.1.1]propellane,
process
uniquely
enabled
by
photochemical
prowess
an
electron
donor–acceptor
(EDA)
complex.
This
method
is
distinguished
its
minimalist
yet
powerful
approach:
devoid
transition
metals,
additives,
photosensitizers.
Its
universality
further
exemplified
seamless
compatibility
broad
spectrum
halides
heteroarenes
under
standardized
conditions,
heralding
new
era
synthetic
versatility.
The
method's
practicality
underscored
capacity
late-stage
modification
pharmaceuticals,
offering
transformative
tool
enhancement
existing
drug
molecules.
Moreover,
facile
derivatization
synthesized
products
underscores
adaptability
potential
diverse
applications.
Our
mechanistic
studies
have
elucidated
underlying
radical-relay
pathway,
pinpointing
pivotal
role
EDA
complex
in
initiating
transformation.
discovery
not
only
enriches
our
fundamental
understanding
but
also
opens
avenues
strategic
optimization.
Organic Chemistry Frontiers,
Journal Year:
2024,
Volume and Issue:
unknown
Published: Jan. 1, 2024
This
study
describes
a
pioneering
visible-light-induced
phosphine-catalyzed
halogen-atom
transfer
(XAT)
strategy
that
heralds
new
era
in
the
difunctionalization
of
[1.1.1]propellane.
Organic Chemistry Frontiers,
Journal Year:
2025,
Volume and Issue:
unknown
Published: Jan. 1, 2025
Herein,
an
environmentally
friendly
methodology
has
been
established
for
the
photoelectrochemical
chlorination
of
C(sp
2
)–H
bonds
in
quinolinone
derivatives
using
PVC
plastic
waste
as
chlorine
source.
Green Chemistry,
Journal Year:
2024,
Volume and Issue:
26(12), P. 7419 - 7423
Published: Jan. 1, 2024
We
have
developed
a
straightforward
electrochemical
protocol
for
direct
α-amidation
and
α-pyrazolation
of
N
-alkoxy-
-aryloxycarbonyl
pyrrolidines
with
amides
or
pyrazoles.
The Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
unknown
Published: Nov. 25, 2024
Herein,
the
first
example
of
self-catalyzed
sono-photoinduced
carbon-carbon
bond
formation
was
described.
Combining
advantages
phototriggered
self-catalysis
and
ultrasonic
catalysis,
a
wide
range
3-arylquinoxalin-2(1
