Abstract
Spirocyclobutyl
oxindoles,
characterized
by
their
unique
three‐dimensional
structures,
are
valuable
building
blocks
for
many
pharmacophores
and
drug
units.
However,
stereoselective
synthetic
strategies
these
scaffolds
remain
underdeveloped,
with
most
existing
methods
relying
on
transition
metal
catalysts
stoichiometric
redox
reagents.
In
this
work,
we
introduce
an
electrochemical
strain‐release
driven
cascade
spirocyclization
of
bicyclo[1.1.0]butane
(BCB)
derivatives
the
synthesis
functionalized
spirocyclobutyl
oxindoles.
Tetrabutylammonium
bromide
serves
a
dual
purpose
as
both
supporting
electrolyte
brominating
agent.
The
method
offers
broad
substrate
scope,
high
atom
economy,
excellent
diastereoselectivity.
stereoselectivity
product
is
controlled
minimizing
dipolar
repulsion
between
amide
C=O
C−Br
bonds.
We
also
explored
methodology′s
versatility
applying
it
to
various
functionalizations
demonstrated
its
scalability
practical
use.
efficient
derivatization
products
allowed
rapid
creation
diverse
library
Chemical Society Reviews,
Год журнала:
2023,
Номер
52(23), С. 8106 - 8125
Опубликована: Янв. 1, 2023
This
tutorial
review
delves
into
the
unique
advantages
of
electrochemistry
in
context
asymmetric
catalysis,
first
providing
a
brief
introduction
to
electrosynthesis,
then
exploring
representative
case
studies
with
mechanistic
focus.
Abstract
Synthetic
electro‐organic
chemistry
is
advancing
to
a
well‐established
methodology
in
academic
research
and
industry.
The
simple
process
control
minimizes
reagent
waste
avoids
using
toxic
environmentally
unfriendly
redox
agents,
providing
feasible
sustainable
alternative
conventional
techniques.
However,
fundamental
disadvantage,
the
necessity
of
ion‐conductive
components
within
electrolyte.
recovery
these
supporting
electrolytes,
as
well
product
isolation,
pose
challenges
for
work‐up
strategies.
This
review
presents
following
electrochemical
protocols
featuring
material‐
resource‐saving
strategy:
dual
role
electrolytes
conductivity
enabling
reagents
or
meditators.
first
conclude
categorize
strategies
electrolytes.
It
may
inspire
electrochemists
advance
development
optimization
synthesis
towards
more
resource‐efficient
reaction
control.
Chemical Communications,
Год журнала:
2025,
Номер
unknown
Опубликована: Янв. 1, 2025
An
electrochemical
method
for
oxidative
dearomatization
of
electron-deficient
phenols
is
reported,
using
tetrabutylammonium
bromide
as
a
catalytic
mediator
under
aqueous
biphasic
conditions.
Organic Process Research & Development,
Год журнала:
2023,
Номер
27(11), С. 2183 - 2191
Опубликована: Ноя. 6, 2023
A
multigram
electrochemical
method
for
the
Hofmann
rearrangement
of
a
primary
amide
into
methyl
carbamate
was
developed
using
spinning
cylinder
electrode
cell.
The
is
based
on
anodic
oxidation
NaBr,
an
inexpensive
and
readily
available
bromide
source,
circumventing
use
stoichiometric
amounts
oxidants.
process
relies
three-dimensional
anode
material,
graphite
felt,
which
has
been
implemented
assembly.
felt
material
can
efficiently
oxidize
salt
by
oxidation,
initiating
reaction.
Additionally,
motion
provides
excellent
mass
transfer
to
system.
reaction
first
optimized
in
small-scale
undivided
beaker
cell
then
translated
reactor.
Improved
productivity
technology
realized
larger
reactor
with
5-fold
increase
surface
area,
providing
analogous
results
those
obtained
small
Under
optimal
conditions,
high
yields
(95%)
27
g
per
hour
have
attained.
Abstract
In
2014,
the
World
Health
Organization
called
drug
resistance
to
antibiotics
a
“major
global
threat”.
Therefore,
ever‐increasing
human
need
for
new
with
greater
effectiveness
and
fewer
side
effects
is
necessity.
Meanwhile,
sulfonamides
are
among
most
widely
used
in
world.
this
review,
attention
has
been
paid
key
points
raised
various
papers
field
of
electrosynthesis
these
compounds,
considering
their
positive
negative
aspects,
including
interaction
as
much
possible
principles
green
chemistry
absence
environmental
risks,
low
cost
versatility
scalability
method
along
acceptable
efficiency.
following,
we
will
discuss
research
focused
on
synthesis
sulfonamide
derivatives
based
oxidation
or
reduction
compounds
which
take
place
working
electrode
surface.
Molecular Catalysis,
Год журнала:
2024,
Номер
554, С. 113823 - 113823
Опубликована: Янв. 16, 2024
A
reliable
electrochemical
version
for
the
Hofmann
rearrangement
has
been
established,
which
can
be
performed
at
high
current
density
in
simple,
commercial
flow
electrolysis
cells.
The
protocols
have
optimized
towards
both
aromatic
and
aliphatic
substrates,
yielding
good
to
excellent
yields
across
a
broad
substrate
scope.
method
also
easily
multi-gram
scale.
Advanced Synthesis & Catalysis,
Год журнала:
2023,
Номер
365(20), С. 3455 - 3460
Опубликована: Авг. 24, 2023
Abstract
An
electrochemically‐driven
organocatalytic
enantioselective
oxidative
coupling
of
tetrahydroisoquinolines
and
acrylaldehyde
was
developed.
Various
chiral
C1‐alkenyl
derivatives
were
obtained
with
69–86%
yields
93:7–96:4
er.
Notable
features
this
reaction
include
asymmetric
organocatalysis
(5.0
mol%
β‐ICD
as
catalyst),
electricity
the
oxidant,
air
atmosphere,
undivided
cell.
This
synthetic
route
offers
access
to
various
optically
active
C1‐substituted
derivatives.
Organic Chemistry Frontiers,
Год журнала:
2023,
Номер
10(13), С. 3353 - 3360
Опубликована: Янв. 1, 2023
We
herein
reported
an
electrochemical
four-component
aminochlorination,
in
which
benzimidazole
was
demonstrated
to
be
a
reactivity
modulator
for
chlorine
radicals
by
situ
forming
various
N
-chlorobenzimidazole
species.
