Beilstein Journal of Organic Chemistry,
Год журнала:
2024,
Номер
20, С. 1497 - 1503
Опубликована: Июль 3, 2024
We
report
a
practical
and
sustainable
electrophotochemical
metal-catalyzed
protocol
for
decarboxylative
cyanation
of
simple
aliphatic
carboxylic
acids.
This
environmentally
friendly
method
features
easy
availability
substrates,
broad
functional
group
compatibility,
directly
converts
diverse
range
acids
including
primary
tertiary
alkyl
into
synthetically
versatile
alkylnitriles
without
using
chemical
oxidants
or
costly
cyanating
reagents
under
mild
reaction
conditions.
European Journal of Organic Chemistry,
Год журнала:
2023,
Номер
26(21)
Опубликована: Апрель 7, 2023
Abstract
The
exceptional
versatility
of
carboxylic
acids
has
been
extensively
exploited
in
organic
synthesis
across
several
decades.
There
a
recent
upsurge
radical
decarboxylative
transformations.
process
can
be
initiated
under
mild
conditions,
and
the
resultant
radicals
have
orthogonal
reactivities
to
closed‐shell
species,
thus
providing
immense
opportunities
for
streamlining
novel
reactions.
use
free
is
most
desirable
owing
its
high
atom
step
economy.
Aiming
demonstrate
attractiveness
strategy
inspire
chemists
tackle
existing
challenges,
this
review
outlines
advances
on
functionalization
acids.
Chemistry - A European Journal,
Год журнала:
2023,
Номер
29(24)
Опубликована: Янв. 13, 2023
Abstract
In
contrast
to
the
rapid
growth
of
electrophotocatalysis
in
recent
years,
enantioselective
catalytic
reactions
powered
by
this
unique
methodology
remain
rare.
work,
we
report
an
electrophotochemical
metal‐catalyzed
protocol
for
direct
asymmetric
decarboxylative
cyanation
aliphatic
carboxylic
acids.
The
synergistic
merging
cerium
catalysis
and
electrochemical
copper
permits
mild
reaction
conditions
formation
utilization
key
carbon
centered
radicals
combining
power
light
electrical
energy.
Electrophotochemical
enables
radical
decarboxylation
produce
alkyl
radicals,
which
could
be
effectively
intercepted
construction
C−CN
bonds
a
highly
stereoselective
fashion.
This
environmentally
benign
method
smoothly
converts
diverse
array
arylacetic
acids
into
corresponding
nitriles
good
yields
enantioselectivities
without
using
chemical
oxidants
or
pre‐functionalization
acid
substrates
can
readily
scaled
up.
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.
Israel Journal of Chemistry,
Год журнала:
2023,
Номер
64(1-2)
Опубликована: Сен. 27, 2023
Abstract
Recent
years
have
witnessed
a
renaissance
of
organic
electrochemistry
since
the
cheap,
safe,
sustainable
electron
could
be
employed
as
traceless
redox
agent
to
facilitate
conversions.
Additionally,
divergent
selectivity
achieved
by
tuning
potential
or
current
electrochemical
reaction.
Compared
electrooxidation
electroreduction
reactions,
paired
electrolysis
represents
more
practical
and
energy‐efficient
strategy
that
delivers
products
making
use
both
anodic
cathodic
reactions
simultaneously.
This
mini‐review
summarized
breakthroughs
recent
advances
in
this
fascinating
field
mainly
is
divided
into
three
parts:
parallel,
sequential,
convergent
electrolysis.
ACS Catalysis,
Год журнала:
2023,
Номер
13(24), С. 16279 - 16285
Опубликована: Дек. 6, 2023
Photoinduced
nickel-catalyzed
demethylative
cyanation
and
decarboxylative
cyanomethylation
of
aryl
halides
are
described
here.
Commercially
available
bromoacetonitrile
was
found
to
act
as
an
efficient
cyanating
reagent
for
the
photoinduced
reaction
in
absence
a
photocatalyst.
Moreover,
photoredox
nickel
dual-catalyzed
has
also
been
realized
using
cesium
cyanoacetate
under
mild
conditions.
A
series
benzyl
nitriles
bearing
diverse
functional
groups
were
prepared
with
good
high
efficiency.
Organic Letters,
Год журнала:
2023,
Номер
25(17), С. 3023 - 3028
Опубликована: Апрель 27, 2023
Copper-catalyzed
asymmetric
radical
cyanation
reactions
have
emerged
as
a
powerful
strategy
for
rapid
construction
of
α-chiral
nitriles.
However,
the
directly
decarboxylative
common
alkyl
carboxylic
acids
remain
largely
elusive.
Herein,
we
report
protocol
copper-catalyzed
direct
and
enantioselective
benzylic
acids.
The
in
situ
activation
acid
substrates
by
commercially
inexpensive
hypervalent
iodine(III)
reagent
promoted
yield
radicals
under
mild
reaction
conditions
without
prefunctionalization.
structurally
diverse
chiral
nitriles
were
produced
good
yields
with
high
enantioselectivities.
In
addition,
products
can
be
readily
converted
to
other
useful
compounds
via
further
transformations.
Organic Chemistry Frontiers,
Год журнала:
2023,
Номер
11(3), С. 796 - 801
Опубликована: Дек. 5, 2023
A
straightforward
and
practical
strategy
for
decarboxylphosphatization
of
N
-aryl
glycines
to
access
α-amino
phosphine
oxides,
enabled
by
visible-light
photoredox
catalysis
in
the
absence
metal,
base,
has
been
described.
Chemical Communications,
Год журнала:
2023,
Номер
59(36), С. 5447 - 5450
Опубликована: Янв. 1, 2023
A
paired
electrochemical
method
is
presented
for
the
one-pot
synthesis
of
γ,δ-unsaturated
α-amino
esters.
The
involves
in
situ
generation
organozinc
reagents
through
zinc
chloride
reduction
on
nickel
cathode
and
TEMPO-mediated
oxidation
amino
esters
carbon
anode.
presence
an
ester
moiety
amine
substrate
was
found
to
be
crucial
achieving
high
diastereoselectivity.
