Angewandte Chemie,
Год журнала:
2023,
Номер
135(26)
Опубликована: Апрель 22, 2023
Abstract
The
selective
electrochemical
synthesis
of
1
H
‐indazoles
and
their
N
‐oxides
the
subsequent
C−H
functionalization
‐indazole
are
described.
outcomes
were
determined
by
nature
cathode
material.
When
a
reticulated
vitreous
carbon
was
used,
wide
range
selectively
synthesized,
electrosynthesis
products
deoxygenated
to
N‐heteroaromatics,
owing
cathodic
cleavage
N−O
bond
via
paired
electrolysis,
when
Zn
used.
scope
this
protocol
is
broad,
as
both
electron‐rich
electron‐poor
substrates
tolerated.
potency
strategy
demonstrated
through
late‐stage
various
bioactive
molecules,
making
reaction
attractive
for
derivatives
pharmaceutical
research
development.
Detailed
mechanistic
investigations
involving
electron
paramagnetic
resonance
spectroscopy
cyclic
voltammetry
suggested
radical
pathway
featuring
iminoxyl
radicals.
Owing
rich
reactivity
‐oxides,
diverse
reactions
performed.
We
synthetic
utility
synthesizing
molecules
lificiguat
YD
(3);
key
intermediates
bendazac,
benzydamine,
norepinephrine/serotonin
reuptake
inhibitors,
SAM‐531,
gamendazole
analogues;
precursor
organic
light‐emitting
diodes.
ACS Catalysis,
Год журнала:
2024,
Номер
14(8), С. 5735 - 5778
Опубликована: Апрель 1, 2024
The
lack
of
effective
strategies
for
direct
construction
nitrogen–nitrogen
bonds
has
hampered
developments
in
the
synthesis
and
application
molecules
containing
hydrazine
or
azo
motifs.
Attracted
by
their
properties
both
material
science
medicinal
chemistry,
more
attention
been
drawn
to
this
area,
resulting
fast
growth
design
azaheterocycles
substituted
hydrazines.
This
review
focuses
on
efficient
catalytic
approaches
toward
formation
N–N
N═N
through
different
strategies,
including
oxidative
dehydrogenation,
nitrene-transfer
reaction,
reductive
coupling,
some
other
recently
developed
methods.
Abstract
Electrochemistry
became
a
unique
and
powerful
tool
for
the
preparation
of
plethora
valuable
chemical
species
including
functional
materials,
drug
candidates
clinically
approved
pharmaceuticals.
Organic
electrosynthesis
well
satisfies
main
goals
green
chemistry
development
is
considered
as
one
useful
approaches
toward
creation
sustainable
future.
Since
nitrogen
heterocyclic
scaffolds
still
retain
their
importance
construction
novel
materials
medications,
emerging
trends
in
organic
electrochemistry
discovery
synthetic
methods
assembly
subunits.
In
this
regard,
provides
an
efficient
platform
environmentally
benign
generation
various
nitrogen‐centered
radicals
which
are
prominent
intermediates
synthesis
heterocycles.
Review,
recent
developments
heterocycles
via
electrochemical
summarized.
The
special
emphasis
devoted
to
influence
solvent,
electrodes
electrolytes
on
step,
since
these
crucial
parameters
regulate
process
efficiency.
Angewandte Chemie International Edition,
Год журнала:
2023,
Номер
62(26)
Опубликована: Апрель 22, 2023
Abstract
The
selective
electrochemical
synthesis
of
1
H
‐indazoles
and
their
N
‐oxides
the
subsequent
C−H
functionalization
‐indazole
are
described.
outcomes
were
determined
by
nature
cathode
material.
When
a
reticulated
vitreous
carbon
was
used,
wide
range
selectively
synthesized,
electrosynthesis
products
deoxygenated
to
N‐heteroaromatics,
owing
cathodic
cleavage
N−O
bond
via
paired
electrolysis,
when
Zn
used.
scope
this
protocol
is
broad,
as
both
electron‐rich
electron‐poor
substrates
tolerated.
potency
strategy
demonstrated
through
late‐stage
various
bioactive
molecules,
making
reaction
attractive
for
derivatives
pharmaceutical
research
development.
Detailed
mechanistic
investigations
involving
electron
paramagnetic
resonance
spectroscopy
cyclic
voltammetry
suggested
radical
pathway
featuring
iminoxyl
radicals.
Owing
rich
reactivity
‐oxides,
diverse
reactions
performed.
We
synthetic
utility
synthesizing
molecules
lificiguat
YD
(3);
key
intermediates
bendazac,
benzydamine,
norepinephrine/serotonin
reuptake
inhibitors,
SAM‐531,
gamendazole
analogues;
precursor
organic
light‐emitting
diodes.
European Journal of Organic Chemistry,
Год журнала:
2023,
Номер
26(17)
Опубликована: Март 14, 2023
Abstract
Peroxodicarbonate
represents
a
green
and
largely
underexplored
oxidizer
generated
electrochemically
from
aqueous
carbonate
solutions.
Through
state‐of‐the‐art
electrolyzer
technology,
highly
concentrated
solutions
have
now
become
accessible.
These
were
successfully
employed
as
in
deborolative
hydroxylations.
A
plethora
of
phenols
alcohols
thus
been
synthesized
up
to
99
%
organoboron
compounds
using
only
non‐toxic
solvents.
This
transformation
was
scaled‐up
multi‐gram
batch
sizes.
The Journal of Organic Chemistry,
Год журнала:
2023,
Номер
88(6), С. 3499 - 3508
Опубликована: Март 9, 2023
Rh(III)-catalyzed
C-H/N-H
annulation
and
C-H
allylation
of
phenylindazolones
have
been
realized
by
employing
5-methylene-1,3-dioxan-2-one
4-vinyl-1,3-dioxolan-2-one
as
scalable
cross-coupling
partners,
delivering
functionalized
indazolone
fused
heterocycles
branched
linear
allyl
indazolones
respectively
in
moderate
to
high
yield.
These
divergent
synthesis
protocols
showcase
mild
conditions,
broad
substrate
scope,
functional-group
compatibility.
In
addition,
scale-up
preliminary
mechanistic
exploratory
were
also
accomplished.
Organic & Biomolecular Chemistry,
Год журнала:
2023,
Номер
21(13), С. 2632 - 2652
Опубликована: Янв. 1, 2023
The
recent
advances
in
the
construction
of
N–N
bond
from
primary
and
secondary
amines
via
direct
oxidation
method,
is
an
interest
both
academia
industry
for
preparing
organic
frameworks
such
as
azos,
hydrazines,
indazoles
triazoles.
Angewandte Chemie International Edition,
Год журнала:
2024,
Номер
63(14)
Опубликована: Фев. 17, 2024
Nucleophilic
substitutions
are
fundamentally
important
transformations
in
synthetic
organic
chemistry.
Despite
the
substantial
advances
bimolecular
nucleophilic
(S
JACS Au,
Год журнала:
2024,
Номер
4(6), С. 2188 - 2196
Опубликована: Апрель 18, 2024
Iminophosphoranes
are
commonly
used
reagents
in
organic
synthesis
and
are,
therefore,
of
great
interest.
An
efficient
sustainable
iodide-mediated
electrochemical
N-sulfonyl
iminophosphoranes
from
readily
available
phosphines
sulfonamides
is
reported.
This
method
features
low
amounts
supporting
electrolytes,
inexpensive
electrode
materials,
a
simple
galvanostatic
setup,
high
conversion
rates.
The
broad
applicability
could
be
demonstrated
by
synthesizing
20
examples
yields
up
to
90%,
having
diverse
functional
groups
including
chiral
moieties
biologically
relevant
species.
Furthermore,
electrolysis
was
performed
on
g
scale
run
repetitive
mode
recycling
the
electrolyte,
which
illustrates
suitability
for
large-scale
production.
A
reaction
mechanism
involving
mediation
iodide-based
electrolyte
proposed,
completely
agreeing
with
all
results.
The Journal of Organic Chemistry,
Год журнала:
2023,
Номер
88(7), С. 4334 - 4344
Опубликована: Март 16, 2023
An
inexpensive
electrochemical
induction
system
was
used
for
the
efficient
reductive
defunctionalization
of
sulfoximines
through
a
radical
pathway.
This
practical
and
robust
strategy
could
be
removal
S═N
bond-directing
group
from
various
sulfoximines.
The
practicability
this
method
demonstrated
by
its
mild
conditions,
simple
operation,
one-pot
procedure,
gram-scale
synthesis,
undivided
cell.
Furthermore,
preliminary
mechanistic
studies
suggested
that
reaction
might
proceed
via
homocoupling
denitrification
procedure.
