Cu-Catalyzed Synthesis of Symmetric Diarylamines from Organoboronic Acids Using NaNO2 as the Amino Source
The Journal of Organic Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Март 7, 2025
A
copper-catalyzed
novel
synthesis
of
symmetric
diarylamines
was
achieved
from
aryl
boronic
acids
and
NaNO2.
This
protocol
employs
as
the
commercially
available
arylation
reagents
sodium
nitrite
(NaNO2)
cheap,
stable,
solid
amino
source.
Under
a
simple
ligand-
base-free
copper
catalytic
system
(CuCl
sole
catalyst),
wide
range
could
be
obtained
in
moderate
to
good
yields.
Notably,
use
Na15NO2
produce
15N-labeled
diarylamines,
which
would
otherwise
difficult
prepare
by
known
methods.
Язык: Английский
Easy Access to α,β-Diamino-Substituted Cyclopentenaminones through Copper-Catalyzed Double Amination of Unactivated Cyclic Ketones
The Journal of Organic Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Май 27, 2025
Here,
we
report
a
copper-catalyzed
double
amination
of
unactivated
cyclic
ketones
with
commercially
available
secondary
arylamines
for
the
synthesis
α,β-diamino-substituted
cyclopentenaminones.
The
direct
intermolecular
C-N
bond
formation
reaction
offers
advantages
using
an
inexpensive
copper
catalyst,
high
atom
and
step
economy,
mild
conditions,
convenient
operation.
Mechanistic
experiments
indicate
that
this
α,β-difunctionalization
proceeds
through
oxidative
α-enamination/desaturation
ketone
one
arylamine
molecule
to
form
α-enaminone
intermediate,
followed
by
another
molecule.
Язык: Английский
Tosylhydrazide-Induced 1,6-Enyne Radical Cyclization under Copper Catalysis: Access to 3,4-Dihydronaphthalen-1(2H)-one Derivatives
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
unknown
Опубликована: Авг. 30, 2024
We
describe
an
approach
to
access
4-aroyl-3-aryl-3,4-dihydronaphthalen-1(2H)-one
derivatives
in
41–79%
yields
through
the
Cu-catalyzed
radical
cyclization/desulfonylation
of
1,6-enynes
with
tosylhydrazide
under
air
conditions.
This
alternative
desulfonylation
strategy
combines
mild
conditions,
external
oxidant-free
processes,
and
sustainability,
contributing
more
environmentally
friendly
organic
synthesis.
The
mechanistic
studies
showed
that
CuCl/O2
combination
serves
as
source
oxygen
atom
needed
form
C═O
bond.
existence
is
crucial
for
this
conversion.
Язык: Английский
N-Hydroxyphthalimides as Nitrogen Radical Precursors in the Copper-Catalyzed Radical Cross-Coupling Amination of Arylboronic Acids: Synthesis of Arylamines
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
unknown
Опубликована: Ноя. 27, 2024
A
new
and
practical
approach
for
the
synthesis
of
arylamines
via
copper-catalyzed
radical
cross-coupling
amination
arylboronic
acids
has
been
developed.
The
key
enabling
advance
in
this
protocol
is
design
Язык: Английский
Overview of Phenylhydrazine‐Based Organic Transformations
ChemistrySelect,
Год журнала:
2024,
Номер
10(1)
Опубликована: Дек. 30, 2024
Abstract
Phenylhydrazines,
comprised
of
a
phenyl
group
attached
with
hydrazine
unit,
contribute
potentially
to
organic
synthetic
transformations.
Because
the
myriad
applications,
last
decade
has
witnessed
considerable
upsurge
interest
perform
various
reactions
catalyzed/mediated/promoted
by
phenylhydrazines.
Some
these
have
shown
high
regioselectivity
in
short
reaction
time
under
mild
conditions.
The
emergence
innumerable
transformations
utilizing
phenylhydrazine
unleashed
numerous
openings
for
development
diverse
heterocyclic
scaffolds.
Given
importance
this
valuable
chemical
entity,
review
highlights
methodologies
Moreover,
present
article
will
considerably
synthesis
as
well
pharmaceutical
chemistry.
Academically,
be
interesting
and
informative
researchers
attempting
develop
new
routes
structures.
Язык: Английский