The Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
89(17), P. 11959 - 11974
Published: Aug. 27, 2024
Divergent
synthesis
of
structurally
different
products
from
the
same
kinds
starting
materials
is
highly
synthetically
useful
but
very
challenging.
Herein,
we
reported
a
base-mediated
chemodivergent
[4
+
1]
and
[2
cycloaddition
N-alkylpyridinium
enone
under
mild
conditions,
leading
to
furan-fused
bicycles
with
high
diastereoselectivity
spirobicycles,
respectively,
moderate
yields.
N-Alkylpyridinium
salts
were
modular
nucleophilic
transfer
reagents
C1
synthons,
which
underwent
tandem
Michael
addition
α,β-unsaturated
ketones
cyclization
base
conditions.
Late-stage
derivatization
4-propyldicyclohexylanone
an
important
industrial
raw
liquid
crystal
display
(LCD)
screens
was
realized.
In
vitro,
compound
3f
exhibited
good
activities
against
human
colon
cancer
cells
(HCT116)
IC50
values
in
9.82
±
0.27
μM.
Further
biological
evaluations
investigated
mechanism
effective
inhibition
cell
growth,
including
apoptosis
ratio
detection,
cycle
analysis,
migration
capacity
HCT116
cells.
effect
studies,
complex
increased
percentage
apoptotic
26.8%
(15
μM).
The Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
89(9), P. 6117 - 6125
Published: April 24, 2024
The
first
paired
electrolysis-enabled
arylation
of
quinoxalin-2(1H)-ones
was
achieved
using
cyanoarenes
as
the
reagents.
A
variety
3-arylquinoxalin-2(1H)-ones
with
various
important
functional
groups
were
obtained
in
moderate
to
good
yields
under
metal-
and
chemical
oxidant-free
conditions.
With
a
pair
reductive
oxidative
processes
occurring
among
substrates
reaction
intermediates,
power
consumption
can
be
dramatically
reduced.
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.
The Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
89(6), P. 4113 - 4119
Published: March 6, 2024
The
first
example
of
an
electrochemical
multicomponent
synthesis
selenium-containing
compounds
with
inexpensive
and
abundant
elemental
selenium
as
the
selenating
reagent
was
developed.
A
variety
selenazol-2-amines
were
constructed
in
high
yields
good
functional
group
tolerance
under
metal-free
chemical
oxidant-free
conditions.
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.
The Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
89(12), P. 8632 - 8640
Published: June 6, 2024
Herein,
we
disclosed
a
highly
efficient
pathway
toward
3-selenylated
chromone
derivatives
via
electrocatalytic
cascade
selenylation/cyclization/deamination
of
2-hydroxyaryl
enaminones
with
diselenides.
This
method
showed
mild
conditions,
easy
operation,
wide
substrate
scope,
and
good
functional
group
tolerance.
Furthermore,
this
electrosynthesis
strategy
was
amendable
to
scale-up
the
reaction.
Additionally,
preliminary
experiments
revealed
that
reaction
probably
proceeded
cation
instead
radical
pathway.
