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
Iron-Catalyzed Cross-Dehydrogenative Coupling of para-Quinone Methides with Formamides: In Situ Activation of C(sp2)–H Bonds
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(22), С. 16663 - 16678
Опубликована: Ноя. 1, 2024
A
novel
and
straightforward
method
for
the
iron-catalyzed
regioselective
cross-dehydrogenative
coupling
of
para-quinone
methides
(p-QMs)
with
formamides
has
been
developed,
facilitated
by
in
situ
activation
C(sp2)–H
bonds
formyl
alkenyl
substituents
via
a
radical
strategy.
This
does
not
require
preactivation
substrates,
it
can
accommodate
wide
range
p-QMs
under
optimized
reaction
conditions,
resulting
formation
expected
C-7
acetamides-functionalized
moderate
to
good
yields.
The
control
experiments
revealed
that
follows
fundamental
equation
second-order
kinetics.
Additionally,
an
exploration
Hammett
effect
was
undertaken
elucidate
impact
reaction.
In
combination
DFT
calculation,
plausible
mechanism
proposed
through
meticulously
controlled
experiments.
Язык: Английский