The Journal of Organic Chemistry,
Год журнала:
2022,
Номер
87(15), С. 9551 - 9564
Опубликована: Июль 11, 2022
An
atom
economic
method
demonstrates
the
involvement
of
noncovalent
interaction
via
hydrogen
or
halogen
bonding
in
triggering
paired
electrolysis
for
group
transfer
reactions.
Specifically,
this
demonstrated
bromination
several
aromatic
and
heteroaromatic
compounds
through
activation
C(sp3)-Br
bond
organic-bromo
derivatives
on
demand.
This
electrochemical
protocol
is
mild,
mostly
no
additional
electrolyte
needed,
which
makes
workup
process
straightforward.
Unlike
existing
regioselective
monobromination
methods,
work
utilizes
a
relatively
small
amount
(1.2
equiv)
bromine
surrogates
that
releases
demand
under
condition
after
completion
reaction
generates
acetophenone
as
useful
byproduct.
Green
metrics
indicate
has
very
good
efficiency
with
an
E-factor
26.86
kg
waste/1
product.
In
addition
to
scale-up
process,
strategy
could
be
extended
chlorine
thioaryl
units.
extensive
mechanistic
study
accomplished
validate
hypothesis
using
computational,
spectroscopic,
cyclic
voltammetry
studies.
Finally,
applicability
newly
developed
nonbonding
trigger
was
chemoselective
debromination
dihalo
organic
compounds.
Chemical Communications,
Год журнала:
2023,
Номер
59(56), С. 8719 - 8722
Опубликована: Янв. 1, 2023
Substituted
organoselenium
compounds
are
crucial
structural
motifs
in
pharmaceutical
molecules.
Herein,
we
report
a
metal,
oxidant,
and
base-free
electrochemical
approach
to
access
3-selenylindoles
through
an
oxidative
cyclization
of
2-alkynylanilines
with
diselenides.
This
environmentally
friendly
demonstrates
wide
range
substrate
scope
under
mild
reaction
conditions
undivided
cell
setup.
Organic Chemistry Frontiers,
Год журнала:
2025,
Номер
unknown
Опубликована: Янв. 1, 2025
Herein,
an
environmentally
friendly
methodology
has
been
established
for
the
photoelectrochemical
chlorination
of
C(sp
2
)–H
bonds
in
quinolinone
derivatives
using
PVC
plastic
waste
as
chlorine
source.
The Journal of Organic Chemistry,
Год журнала:
2021,
Номер
86(17), С. 12378 - 12385
Опубликована: Авг. 16, 2021
Without
employing
an
external
oxidant,
the
simple
synthesis
of
3-halochromones
and
various
halogenated
electron-rich
arenes
has
been
realized
with
electrode
oxidation
by
simplest
sodium
halide
(NaX,
X
=
Cl,
Br,
I)
as
halogen
source.
This
electrochemical
method
is
advantageous
for
mild
room
temperature
operation,
environmental
friendliness
well
broad
substrate
scope
in
both
C–H
bond
donor
source
components.
The Chemical Record,
Год журнала:
2021,
Номер
21(9), С. 2502 - 2525
Опубликована: Июнь 21, 2021
Abstract
Electrosynthesis
can
be
considered
a
powerful
and
sustainable
methodology
for
the
synthesis
of
small
organic
molecules.
Due
to
its
intrinsic
ability
generate
highly
reactive
species
under
mild
conditions
by
anodic
oxidation
or
cathodic
reduction,
electrosynthesis
is
particularly
interesting
otherwise
challenging
transformations.
One
such
challenge
installation
fluorinated
alkyl
groups,
which
has
gained
significant
attention
in
medicinal
chemistry
material
science
due
their
unique
physicochemical
features.
Unsurprisingly,
several
electrochemical
fluoroalkylation
methods
have
been
established.
In
this
review,
we
survey
recent
developments
established
field
mono‐,
di‐,
trifluoromethylation,
perfluoroalkylation
Chinese Journal of Chemistry,
Год журнала:
2023,
Номер
41(13), С. 1583 - 1588
Опубликована: Фев. 14, 2023
Comprehensive
Summary
A
new
electrochemical
strategy
for
the
atom
transfer
radical
addition
(ATRA)
of
polychloroalkanes
across
olefins
has
been
realized
by
synergism
paired
electrolysis
and
halogen
bonding
activation.
Notably,
readily
accessible
4,4‐di‐
tert
‐butyl
bipyridine
(dtbpy),
acting
as
a
acceptor,
shifted
reduction
potential
C—Cl
bonds
positively
110
mV.
The
decreased
operating
leads
to
wide
substrate
scope
excellent
functional
group
compatibility.
diverse
array
terminal
internal
alkenes
such
(hetero)aryl
olefins,
unactive
aliphatic
natural
products
drugs‐derived
were
well
compatible.
European Journal of Organic Chemistry,
Год журнала:
2022,
Номер
2022(35)
Опубликована: Май 12, 2022
Abstract
Bromination
of
organic
substances
is
still
an
important
reaction
in
modern
synthetic
chemistry.
In
view
the
increasing
demand
for
sustainable
chemistry,
oxidative
bromination
can
play
role
to
avoid
use
hazardous
molecular
bromine
(Br
2
).
this
review,
a
complete
overview
chemical
oxidants
will
be
provided
which
have
been
used
electrophilic
as
well
radical
brominations,
starting
from
less
bromide
Br(−I);
e.
g.,
HBr
or
salt,
with
focus
on
differences
caused
by
choice
oxidant.
Frontiers in Chemistry,
Год журнала:
2022,
Номер
10
Опубликована: Май 17, 2022
We
report
an
electrochemical
oxidative
intramolecular
cyclization
reaction
between
2-alkynylphenol
derivatives
and
different
diselenides
species
to
generate
a
wide
variety
of
substituted-benzo[b]furans.
Driven
by
the
galvanostatic
electrolysis
assembled
in
undivided
cell,
it
provided
efficient
transformation
into
oxidant-,
base-,
metal-free
conditions
open
system
at
room
temperature.
With
satisfactory
functional
group
compatibility,
products
were
obtained
good
excellent
yields.
