The Journal of Organic Chemistry,
Journal Year:
2021,
Volume and Issue:
87(2), P. 1240 - 1248
Published: Dec. 29, 2021
We
present
here
a
rhodium-catalyzed
oxidative
three-point
double
annulation
of
enaminones
with
propargylic
alcohols
via
C–H
and
C–N
bond
activation
to
access
arylnaphthalene-based
lignan
derivatives.
The
key
step
in
the
reaction
is
regioselective
insertion
alcohol
into
rhoda-cycle,
result
hydroxyl
rhodium
coordination.
Necessary
control
experiments
KIE
studies
were
conducted
determine
mechanism.
Advanced Synthesis & Catalysis,
Journal Year:
2023,
Volume and Issue:
365(11), P. 1770 - 1776
Published: March 21, 2023
Abstract
Rh‐catalyzed
C−H
activation
of
arenes
for
oxidative
annulations
with
alkynes
stands
out
as
a
protocol
polycyclic
scaffolds.
This
perspective
drives
us
to
disclose
herein
rhodium
catalyzed
regioselective
triple
annulation
enaminones
hydroxyl‐alkynoates
via
double
functionalization
naphtho‐pyran
Secondary
coordination
OH
in
alkynoate
dictated
the
regioselectivity.
Initial
lactonization
occurred
chemoselectively
on
enamine
part
carbo
rhodation
followed
by
reductive
elimination.
was
scalable
and
has
shown
high
functionality
tolerance.
KIE
studies
were
done
get
insight
mechanism,
some
downstream
transformations
achieved
show
synthetic
potential
method.
Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(29), P. 6209 - 6213
Published: July 12, 2024
Palladium-catalyzed
intermolecular
[3
+
2]
annulation
reactions
via
C-H
activation
represent
a
powerful
and
charming
tool
for
assembling
cyclopentanes.
Herein,
we
have
developed
strategy
the
palladium-catalyzed
alkene-relayed
reaction
of
aryl
iodides
maleimides
C(sp
Angewandte Chemie International Edition,
Journal Year:
2021,
Volume and Issue:
60(52), P. 27005 - 27012
Published: Oct. 20, 2021
Abstract
Herein,
we
disclose
osmaelectrocatalyzed
C−H
activations
that
set
the
stage
for
electrooxidative
alkyne
annulations
by
benzoic
acids.
The
osmium
electrocatalysis
enables
site‐
and
chemoselective
with
unique
levels
of
selectivity.
isolation
unprecedented
osmium(0)
osmium(II)
intermediates,
along
crystallographic
characterization
analyses
spectrometric
spectroscopic
in
operando
techniques
delineate
a
synergistic
redox
catalyst
regime.
Detailed
mechanistic
studies
revealed
facile
cleavage,
which
allows
an
ample
substrate
scope,
providing
provide
robust
user‐friendly
access
to
annulated
heterocycles.
The Journal of Organic Chemistry,
Journal Year:
2021,
Volume and Issue:
87(2), P. 1240 - 1248
Published: Dec. 29, 2021
We
present
here
a
rhodium-catalyzed
oxidative
three-point
double
annulation
of
enaminones
with
propargylic
alcohols
via
C–H
and
C–N
bond
activation
to
access
arylnaphthalene-based
lignan
derivatives.
The
key
step
in
the
reaction
is
regioselective
insertion
alcohol
into
rhoda-cycle,
result
hydroxyl
rhodium
coordination.
Necessary
control
experiments
KIE
studies
were
conducted
determine
mechanism.
