Journal of the American Chemical Society,
Journal Year:
2024,
Volume and Issue:
unknown
Published: Dec. 20, 2024
Complexity-generating
reactions
that
access
three-dimensional
products
from
simple
starting
materials
offer
substantial
value
for
drug
discovery.
While
oxygen-containing
heterocycles
frequently
feature
unique,
nonaromatic
architectures
such
as
spirocyclic
rings,
exploration
of
these
chemical
spaces
is
limited
by
conventional
synthetic
approaches.
Herein,
we
report
a
copper-catalyzed
annulation
and
alkene
transposition
cascade
reaction
enables
modular
preparation
complex,
ethers
readily
available
alkenol
substrates
via
transannular
1,5-hydrogen
atom
transfer-mediated
C–H
functionalization.
Our
transformation
displays
broad
substrate
scope,
shows
excellent
heteroatom
compatibility,
constructs
spirocycles
varying
ring
sizes.
The
wider
utility
this
method
highlighted
numerous
product
diversifications
short
synthesis
the
all-carbon
framework
spirotenuipesine
A.
We
anticipate
can
significantly
streamline
to
privileged
class
will
find
application
in
natural
synthesis.
European Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
unknown
Published: Sept. 4, 2024
Abstract
Acridine
scaffolds
are
present
in
biological
and
pharmaceutical
molecules.
However,
achieving
asymmetric
functionalization
of
acridines
remains
challenging
without
an
efficient
highly
stereoselective
approach.
Here
we
demonstrate
a
facile
electrooxidative
dehydrogenative
coupling
reaction
9,10‐dihydroacridines
with
aldehydes.
This
method
offers
sustainable
effective
route
to
various
chiral
α‐alkylation
high
yields
excellent
enantioselectivities
facilitated
by
readily
available
aminocatalyst.
Detailed
mechanistic
studies
cyclic
voltammetric
analyses
reveal
that
this
electrochemical
proceeds
through
redox‐mediated
oxidation,
followed
nucleophilic
attack
concurrently
generated
enamine.
We
anticipate
our
research
will
open
avenues
for
promising
exploration
organocatalyzed
enantioselective
transformations.
Green Chemistry,
Journal Year:
2024,
Volume and Issue:
unknown
Published: Jan. 1, 2024
A
metal-
and
oxidizing
reagent-free
electrochemical
dehydrogenative
annulation
of
enamides
with
O
-nucleophiles
has
been
developed,
leading
to
a
series
4-oxo-oxazolines
under
environmentally
friendly
conditions.
Journal of the American Chemical Society,
Journal Year:
2024,
Volume and Issue:
unknown
Published: Dec. 19, 2024
Adiponitrile
(ADN)
has
wide
applications,
especially
in
the
polymer
industry.
With
substantial
and
increasing
global
demand
for
ADN,
effective
production
of
ADN
using
safe
abundant
starting
materials
is
highly
desirable
but
very
challenging.
Herein,
we
discovered
that
CuBr,
combined
with
1,10-phenanthroline
(phen),
could
effectively
promote
ammoxidation
reaction
cyclohexanone
to
a
yield
>99%
aqueous
ammonia
as
nitrogen
source
O
Journal of the American Chemical Society,
Journal Year:
2024,
Volume and Issue:
unknown
Published: Dec. 20, 2024
Complexity-generating
reactions
that
access
three-dimensional
products
from
simple
starting
materials
offer
substantial
value
for
drug
discovery.
While
oxygen-containing
heterocycles
frequently
feature
unique,
nonaromatic
architectures
such
as
spirocyclic
rings,
exploration
of
these
chemical
spaces
is
limited
by
conventional
synthetic
approaches.
Herein,
we
report
a
copper-catalyzed
annulation
and
alkene
transposition
cascade
reaction
enables
modular
preparation
complex,
ethers
readily
available
alkenol
substrates
via
transannular
1,5-hydrogen
atom
transfer-mediated
C–H
functionalization.
Our
transformation
displays
broad
substrate
scope,
shows
excellent
heteroatom
compatibility,
constructs
spirocycles
varying
ring
sizes.
The
wider
utility
this
method
highlighted
numerous
product
diversifications
short
synthesis
the
all-carbon
framework
spirotenuipesine
A.
We
anticipate
can
significantly
streamline
to
privileged
class
will
find
application
in
natural
synthesis.
