C–O Coupling of Hydrazones with Diacetyliminoxyl Radical Leading to Azo Oxime Ethers—Novel Antifungal Agents
Molecules,
Год журнала:
2023,
Номер
28(23), С. 7863 - 7863
Опубликована: Ноя. 30, 2023
Selective
oxidative
C-O
coupling
of
hydrazones
with
diacetyliminoxyl
is
demonstrated,
in
which
plays
a
dual
role.
It
an
oxidant
(hydrogen
atom
acceptor)
and
O-partner
for
the
coupling.
The
reaction
completed
within
15-30
min
at
room
temperature,
compatible
broad
scope
hydrazones,
provides
high
yields
most
cases,
requires
no
additives,
makes
it
robust
practical.
proposed
leads
to
novel
structural
family
azo
compounds,
oxime
ethers,
were
discovered
be
highly
potent
fungicides
against
spectrum
phytopathogenic
fungi
(Venturia
inaequalis,
Rhizoctonia
solani,
Fusarium
oxysporum,
moniliforme,
Bipolaris
sorokiniana,
Sclerotinia
sclerotiorum).
Язык: Английский
N‐Oxyl Radicals in Oxidative C–O Coupling: Free‐Radical Hydrogen Substitution and Addition to C=C Bonds
Asian Journal of Organic Chemistry,
Год журнала:
2024,
Номер
unknown
Опубликована: Окт. 18, 2024
Abstract
N
‐oxyl
radicals
occupy
an
important
place
in
free‐radical
oxidative
CH‐functionalization
being
one
of
the
most
efficient
redox‐organocatalysts
for
hydrogen
atom
abstraction
(HAT).
Their
applications
include
aerobic
radical
chain
autoxidation,
with
formation
carbon‐carbon
and
carbon‐heteroatom
bonds.
The
persistent
nature
N‐
oxyl
combined
their
high
reactivity
HAT
results
unique
dual
chemistry:
same
can
both
propagate
reaction
(at
low
concentrations)
effectively
“terminate”
carbon‐centered
higher
concentrations).
latter
case
opens
a
new
synthetic
application
area
radicals,
which
they
act
as
abstracting
species
O‐reagents
cross‐coupling
thus
produced.
Apart
from
C−H
bond
cleavage,
reactive
have
been
extensively
used
recently
C=C
double
functionalization
via
addition
reactions.
In
this
review,
reactions
introduction
fragments
alkene
difunctionalizations
by
oxyls
are
covered
emphasis
on
relationship
between
conditions
selectivity.
Язык: Английский
Manganese‐ Mediated Cascade Radical Oxidative Cyclization/1,6‐Conjugate Addition of Unsaturated Oximes with p‐Quinone methides: Facile Access to β,β‐Diarylmethine Isoxazolines
Chemistry - An Asian Journal,
Год журнала:
2024,
Номер
unknown
Опубликована: Ноя. 9, 2024
A
simple
and
efficient
strategy
for
the
synthesis
of
structurally
diverse
β,β-diarylmethine
substituted
isoxazoline
derivatives
have
been
developed.
This
approach
employs
a
manganese-promoted
oxidative
cyclization
coupled
with
1,6-conjugate
addition
unsaturated
oximes
to
p-quinone
methides.
The
key
features
this
study
include
formation
C-O
C-C
bonds
through
intramolecular
intermolecular
interactions,
facilitated
by
in
situ
generated
iminoxyl
radicals.
isoxazolines,
bearing
wide
range
functional
groups,
were
isolated
high
yields.
Язык: Английский
Electrochemically Induced Synthesis of N-Allyloxyphthalimides via Cross-Dehydrogenative C–O Coupling of N-Hydroxyphthalimide with Alkenes Bearing the Allylic Hydrogen Atom
ACS Omega,
Год журнала:
2024,
Номер
9(50), С. 49825 - 49831
Опубликована: Дек. 2, 2024
The
electrochemically
induced
reaction
between
alkenes,
bearing
an
allylic
hydrogen
atom,
and
N-hydroxyphthalimide
was
investigated.
Cross-dehydrogenative
C–O
coupling
with
phthalimide-N-oxyl
radical,
derived
from
N-hydroxyphthalimide,
occurs
instead
of
oxidation
the
site,
formation
a
carbonyl
group
or
functionalization
double
C═C
bond.
discovered
transformation
proceeds
in
undivided
electrochemical
cell
equipped
carbon
felt
anode
platinum
cathode.
Coupling
products
were
obtained
yields
up
to
79%.
developed
process
is
based
on
abstraction
atom
position
for
while
bond
remains
unreacted.
method
exploits
ability
radical
abstract
atoms
following
interception
intermediate
C-centered
radical.
Язык: Английский