Energy Transfer (EnT)-Mediated Stereoselective Aryl-Heterofunctionalization of Unactivated Alkynes via Radical Rearrangement
The Journal of Organic Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Янв. 5, 2025
In
this
study,
we
present
a
novel
catalyst-free
energy
transfer
mediated
radical
rearrangement
strategy
for
the
aryl-heterofunctionalization
of
unactivated
alkynes,
leading
to
synthesis
polyfunctional
olefins
with
exceptional
stereoselectivity.
This
innovative
approach,
driven
by
visible
light,
exemplifies
green
chemistry
principles
eliminating
reliance
on
transition
metals,
external
oxidants,
and
photocatalysts.
The
broad
applicability
our
method
is
demonstrated
through
successful
diverse
array
compounds,
including
vinyl
sulfones,
selenides,
sulfides.
Preliminary
mechanistic
insights
suggest
an
mechanism,
highlighting
efficiency
selectivity
strategy.
Язык: Английский
Metal-Free Visible-Light Excitation of TMSN3 Enables [3 + 2] Cycloaddition of Arylidenecyclopropanes with Olefins
Organic Letters,
Год журнала:
2025,
Номер
unknown
Опубликована: Апрель 14, 2025
A
visible-light
photoredox
[3
+
2]
cycloaddition
reaction
of
arylidenecyclopropanes
with
olefins
was
developed,
employing
the
readily
available
and
commercially
accessible
TMSN3
as
an
efficient
radical
mediator.
This
method
provides
a
convenient
route
to
arylidenecyclopentanes
from
starting
materials,
is
metal-free,
features
enhanced
atom
step
economy,
excellent
selectivity,
extensive
substrate
versatility,
favorable
functional
group
compatibility,
structural
diversity,
mild
conditions,
which
further
enable
late-stage
diversification.
DFT
calculations
elucidated
that
this
transformation
entails
sequential
generation,
addition,
ring-opening,
cyclization,
elimination
steps.
Язык: Английский
Electrochemically Induced Synthesis of Substituted 5-Thiotetrazoles
The Journal of Organic Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Май 6, 2025
A
novel
electrochemical
procedure
for
the
one-pot
synthesis
of
variously
substituted
5-thiotetrazole
has
been
established
by
a
three-component
reaction
(thiol(thiophenol)s,
isocyanides,
and
azidotrimethylsilane).
This
approach
is
achieved
sulfidation
isocyanide
subsequent
cycloaddition
with
azidotrimethylsilane
under
mild
conditions
without
metal
catalyst
or
external
oxidant.
Importantly,
presented
methodology
not
only
features
wide
substrate
scope
but
also
exhibits
practicality
showcased
gram-scale
various
conversions.
Язык: Английский