Electrochemical Three-Component C–H Functionalization of Indoles with Sodium Bisulfite and Alcohols to Access Indole-Containing Sulfonate Esters
The Journal of Organic Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Янв. 4, 2025
Herein,
an
efficient
electrochemical
three-component
C-H
functionalization
of
indoles
with
sodium
bisulfite
and
alcohols
is
described,
providing
a
sustainable
convenient
synthetic
route
for
the
construction
structurally
valuable
indole-containing
sulfonate
esters
in
moderate
to
good
yields.
This
protocol
proceeds
undivided
cell
without
any
metal
catalysts
or
oxidants,
features
broad
substrate
scope,
has
excellent
functional
group
tolerance.
Preliminary
mechanistic
studies
suggest
that
radical-radical
pathway
may
be
involved
this
reaction
system.
Язык: Английский
Visible-Light-Promoted Oxidative Decarboxylative Acylation of Acenaphthenone-2-ylidene ketones with α-Keto Carboxylic Acids under Metal , Additonal Oxidant and Base-free condition
Tetrahedron,
Год журнала:
2025,
Номер
unknown, С. 134674 - 134674
Опубликована: Апрель 1, 2025
Язык: Английский
Electrochemical synthesis of allenyl silanes and allenyl boronic esters
Nature Communications,
Год журнала:
2025,
Номер
16(1)
Опубликована: Май 17, 2025
Allenyl
silanes
and
boronates
are
pivotal
building
blocks
in
organic
synthesis.
Nevertheless,
their
synthesis
requires
the
manipulation
of
transition
metal
or
highly
reactive
species.
Hence,
development
more
sustainable
protocol
is
sought
after.
Here
we
show
electrochemical
allenyl
boronic
esters.
This
catalyst-free
method
proceeds
under
mild
reaction
conditions.
The
for
shows
an
excellent
efficiency
a
good
functional
group
tolerance.
isolated
yields
(28
examples,
45-95%
yields)
without
use
catalyst
A
similar
developed
boronates,
which
obtained
low
to
moderate
(13
5-55%
yields).
Finally,
mechanism
based
on
oxidative
generation
silyl
boryl
radicals
suggested
access
these
classes
allenes.
Язык: Английский
DABCO‐Mediated Photoelectrochemical Three‐Component Sulfonocyclization of 3‐Aza‐1,5‐dienes
Lu-Cai Ding,
Gui-Hong Yang,
Li Luo
и другие.
Chinese Journal of Chemistry,
Год журнала:
2024,
Номер
unknown
Опубликована: Дек. 2, 2024
Comprehensive
Summary
Herein,
we
report
a
rare
example
of
three‐component
net‐oxidative
sulfonylation
SO
2
surrogate
with
an
oxidatively
activated
radical
precursor
under
mild
and
metal‐
external‐oxidant‐free
conditions.
The
mildness
sustainability
the
reaction
are
enabled
by
photoelectrocatalysis,
3‐aza‐1,5‐dienes,
organotrifluoroborates
1,4‐diazabicyclo[2.2.2]octane
bis(sulfur
dioxide)
adduct
(DABSO)
undergo
sulfonylative
cyclization
to
afford
sulfono
4‐pyrrolin‐2‐ones
in
atom‐economical
manner
broad
substrate
scope
good
functional‐group
tolerance.
protocol
is
amenable
late‐stage
diversification
complex
molecular
architectures
as
well
gram‐scale
synthesis.
Sunlight
could
be
used
light
source,
conducted
all‐solar
mode
using
commercially
available
photovoltaic
panel
generate
electricity
situ
.
Mechanistic
studies
reveal
that
generated
(DABCO),
which
was
generally
innocent
previous
reactions,
functions
electron
shuttle
between
photocatalytic
cycle
reactants.
Язык: Английский
Electrophotocatalytic Thiocyanation and Sulfonylation Cyclization of Unactivated Alkenes
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
unknown
Опубликована: Дек. 18, 2024
We
report
an
electrophotocatalytic
process
that
enables
the
thiocyanation
and
sulfonylation/cyclization
of
alkenes.
It
is
applicable
to
a
wide
range
unactivated
alkenes,
using
inexpensive
photocatalyst
2,4,6-triphenylpyrylium
tetrafluoroborate
(TPPT)
produce
diverse
array
heterocycles
containing
sulfonyl
thiocyano
groups
with
good
functional
group
tolerance.
The
protocol
operates
under
mild,
chemical
oxidant-
transition-metal-free,
broad
scope
substrates.
Preliminary
mechanistic
studies
suggest
reaction
involves
combination
electrolysis
reductive
quenching
photocatalytic
cycle
TPPT.
Язык: Английский