Angewandte Chemie,
Journal Year:
2024,
Volume and Issue:
unknown
Published: Nov. 13, 2024
Abstract
Amino
alcohols,
particularly
remote
amino
alcohols
and
peptide
are
valuable
due
to
their
functional
diversity
in
biologically
active
compounds.
However,
traditional
synthesis
methods
face
significant
challenges,
making
electrochemistry
an
attractive
alternative.
We
have
developed
a
mild
biocompatible
sequential
paired
electrolysis
strategy,
leveraging
copper‐electrocatalysis
synthesize
diverse
including
unnatural
alcohols.
Both
experimental
results
density
theory
(DFT)
calculations
demonstrated
that
water
serves
as
both
the
hydroxyl
source
solvent,
facilitating
generation
of
CuH
with
Cu(I)
at
cathode,
which
turn
reduces
aldehyde
intermediates
formed
during
reaction.
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.
Chemical Society Reviews,
Journal Year:
2025,
Volume and Issue:
unknown
Published: Jan. 1, 2025
This
review
highlights
organo-mediators
that
enable
electrochemical
reactions
via
outer-sphere
electron
transfer
(ET),
offering
advantages
such
as
availability,
tunability,
and
simplified
post-processing
compared
to
direct
electrolysis.
Angewandte Chemie International Edition,
Journal Year:
2024,
Volume and Issue:
unknown
Published: Nov. 13, 2024
Abstract
Amino
alcohols,
particularly
remote
amino
alcohols
and
peptide
are
valuable
due
to
their
functional
diversity
in
biologically
active
compounds.
However,
traditional
synthesis
methods
face
significant
challenges,
making
electrochemistry
an
attractive
alternative.
We
have
developed
a
mild
biocompatible
sequential
paired
electrolysis
strategy,
leveraging
copper‐electrocatalysis
synthesize
diverse
including
unnatural
alcohols.
Both
experimental
results
density
theory
(DFT)
calculations
demonstrated
that
water
serves
as
both
the
hydroxyl
source
solvent,
facilitating
generation
of
CuH
with
Cu(I)
at
cathode,
which
turn
reduces
aldehyde
intermediates
formed
during
reaction.
The
formation
of
carbon-carbon
(C–C)
bonds
is
a
cornerstone
organic
synthesis.
Among
various
methods
to
construct
Csp2–Csp3
bonds,
the
reductive
Heck
reaction
between
(hetero)aryl
halides
and
alkenes
stands
out
due
its
potential
efficiency
broad
substrate
availability.
However,
traditional
reactions
are
limited
by
use
pre-cious
metal
catalysts
and/or
aryl
halide
alkene
compatibility.
Here,
we
present
an
electrochemically
mediat-ed,
metal-
catalyst-free
that
tolerates
both
unactivated
diverse
al-kenes
such
as
vinyl
boronates.
Detailed
electrochemical
deuterium-labeling
studies
support
this
transformation
likely
proceeds
through
paired
electrolysis
pathway,
in
which
acid
generated
oxidation
N,N-diisopropylethylamine
(DIPEA)
at
anode
intercepts
alkyl
carbanion
formed
after
radical-polar
crossover
cathode.
As
such,
approach
offers
sustainable
method
for
construction
from
alkenes,
paving
way
development
other
mediated
olefin
difunctionalization
reactions.
Angewandte Chemie,
Journal Year:
2024,
Volume and Issue:
136(38)
Published: June 20, 2024
Abstract
The
formation
of
carbon‐carbon
(C−C)
bonds
is
a
cornerstone
organic
synthesis.
Among
various
methods
to
construct
Csp
2
−Csp
3
bonds,
the
reductive
Heck
reaction
between
(hetero)aryl
halides
and
alkenes
stands
out
due
its
potential
efficiency
broad
substrate
availability.
However,
traditional
reactions
are
limited
by
use
precious
metal
catalysts
and/or
aryl
halide
alkene
compatibility.
Here,
we
present
an
electrochemically
mediated,
metal‐
catalyst‐free
that
tolerates
both
unactivated
diverse
such
as
vinyl
boronates
silanes.
Detailed
electrochemical
deuterium‐labeling
studies
support
this
transformation
likely
proceeds
through
paired
electrolysis
pathway,
in
which
acid
generated
oxidation
N
,
‐diisopropylethylamine
(DIPEA)
at
anode
intercepts
alkyl
carbanion
formed
after
radical‐polar
crossover
cathode.
As
such,
approach
offers
sustainable
method
for
construction
from
alkenes,
paving
way
development
other
mediated
olefin
difunctionalization
reactions.
ChemElectroChem,
Journal Year:
2024,
Volume and Issue:
11(17)
Published: Aug. 1, 2024
Abstract
The
aim
of
this
investigation
was
to
explore
the
possibility
perform
an
asymmetric
reduction,
utilising
a
CBS
‐type
catalyst,
prochiral
aryl
methyl
ketones
under
electrochemical
conditions
generate
needed
BH
3
upon
oxidation
NaBH
4
with
in
situ
generated
I
2
anode
compartment.
Therefore,
various
parameters
were
optimised
conduct
desired
formation
chiral
secondary
alcohols
high
quantitative
yields
stereochemical
induction,
although
catalyst
loading
had
be
chosen
relatively
concur
racemic
reduction
by
electrogenerated
.
The Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
89(17), P. 12769 - 12774
Published: Aug. 14, 2024
Herein,
the
work
demonstrates
an
electrochemically
paired
electrolysis
approach
facilitating
efficient
achievement
of
electrooxidative
1,3-oxo/carboamination
arylcyclopropanes
under
mild
conditions.
The
formation
1,3-arylamination
involves
commercially
available
amine
redox
mediators
through
a
radical–radical
process.
In
addition,
successful
execution
β-amino
ketones
also
occurs
atmospheric
control
experiments
supported
existence
key
benzylic
radical
intermediates
in
reaction
pathway.
