European Journal of Organic Chemistry,
Год журнала:
2022,
Номер
2022(44)
Опубликована: Окт. 24, 2022
Abstract
We
report
a
direct
azidation
of
benzylic
C(sp
3
)−H
bonds
via
an
electrochemical
process,
which
use
cheap
and
durable
graphite
plates
as
electrodes,
without
any
external
oxidants
or
metal
catalysts.
This
protocol
is
novel,
green
environmentally
benign
synthetic
strategy
to
achieve
in
group.
More
importantly,
these
products
are
suitable
for
late‐stage
functionalization
afford
diversified
triazole
tetrazole
derivatives.
Organic Letters,
Год журнала:
2023,
Номер
25(9), С. 1353 - 1358
Опубликована: Март 1, 2023
A
practical
electrochemical
method
for
the
rapid,
safer,
and
mild
synthesis
of
tertiary
hindered
alkyl
fluorides
from
carboxylic
acids
has
been
developed
without
need
hydrofluoric
acid
salts
or
non-glass
reactors.
In
this
anodic
fluorination,
collidinium
tetrafluoroborate
acts
as
both
supporting
electrolyte
fluoride
donor.
wide
range
functional
groups
shown
to
be
compatible,
possibility
scale-up
using
flow
electrochemistry
also
demonstrated.
Angewandte Chemie International Edition,
Год журнала:
2023,
Номер
62(40)
Опубликована: Авг. 19, 2023
Abstract
The
selective
oxygenation
of
ubiquitous
C(sp
3
)−H
bonds
remains
a
highly
sought‐after
method
in
both
academia
and
the
chemical
industry
for
constructing
functionalized
organic
molecules.
However,
it
is
extremely
challenging
to
selectively
oxidize
certain
bond
afford
alcohols
due
presence
multiple
with
similar
strength
steric
environment
molecules,
alcohol
products
being
prone
further
oxidation.
Herein,
we
present
practical
cost‐efficient
electrochemical
monooxygenation
benzylic
using
continuous
flow
reactors.
reactions
produce
trifluoroacetate
esters
that
are
resistant
oxidation
but
undergo
facile
hydrolysis
during
aqueous
workup
form
alcohols.
exhibits
broad
scope
exceptional
site
selectivity
requires
no
catalysts
or
oxidants.
Furthermore,
demonstrates
excellent
scalability
by
producing
115
g
one
products.
high
originates
from
its
unique
mechanism
cleave
through
sequential
electron/proton
transfer,
rather
than
commonly
employed
hydrogen
atom
transfer
(HAT).
Organic Letters,
Год журнала:
2024,
Номер
26(3), С. 653 - 657
Опубликована: Янв. 16, 2024
Amide
bonds
are
ubiquitous
and
found
in
a
myriad
of
functional
molecules.
Although
formed
reliable
robust
fashion,
alternative
amide
bond
disconnections
provide
flexibility
synthetic
control.
Herein
we
describe
an
electrochemical
method
to
form
the
non-amide
C–N
from
direct
benzylic
C(sp3)–H
amidation.
Our
approach
is
applied
toward
synthesis
secondary
amides
by
coupling
substrates
with
substituted
primary
benzamides.
The
reaction
has
been
scaled
up
multigram
scale
flow.
Organic Letters,
Год журнала:
2023,
Номер
25(18), С. 3308 - 3313
Опубликована: Май 2, 2023
A
scalable
electrochemical
difunctionalization
of
gem-difluoroalkenes
to
structurally
versatile
difluoro
motifs
was
achieved.
This
methodology
features
reagent-free
conditions,
good
functional
group
tolerance,
and
a
relatively
broad
substrate
scope.
Meanwhile,
the
electrolysis
protocol
is
easy
handle,
products
show
regio-
chemoselectivity.
The
reaction
mechanism
also
preliminarily
studied.
Green Chemistry,
Год журнала:
2023,
Номер
25(13), С. 5128 - 5133
Опубликована: Янв. 1, 2023
A
unique
electrochemical
four-component
reaction
of
terminal
alkynes,
(thio)xanthenes,
nitriles,
and
water
has
been
established
in
the
absence
any
catalyst
or
external
oxidant.
Organic Letters,
Год журнала:
2023,
Номер
25(23), С. 4252 - 4257
Опубликована: Июнь 2, 2023
An
efficient
electrochemical
dehydrogenative
cross-coupling
of
benzylic
C–H
bonds
with
1-thiosugars
at
room
temperature
is
described.
The
direct
S-glycosylation
protocol
avoids
using
any
oxidant,
which
provides
facile
access
to
various
glycosylated
xanthene
derivatives
up
91%
yield.
This
current
electrooxidative
reaction
characterized
by
high
atom
economy,
efficiency,
mild
conditions,
being
environmentally
benign,
and
excellent
functional
group
tolerance.
Moreover,
preliminary
mechanistic
investigations
reveal
that
the
involves
a
free
radical
process.
Abstract
In
this
study,
we
developed
a
novel
electrochemical
protocol
that
enables
the
functionalization
of
inherently
inert
C(sp
3
)−H
bonds.
protocol,
one‐electron
oxidation
acetic
acid
was
used
to
successfully
generate
methyl
radical,
which
cleaves
benzylic
bonds
substrates
via
hydrogen
atom
transfer
(HAT)
process,
and
further
reaction
with
formed
species
yields
targeted
functionalized
products.
To
best
our
knowledge,
is
first
example
use
in
HAT
process.
Notably
has
environment‐friendly
fine
economy
nature:
driven
by
conditions
absence
expensive
or
hazardous
reagents,
producing
only
gaseous
small
molecules,
hydrogen,
carbon
dioxide,
methane,
as
side
