The Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
88(23), P. 16340 - 16351
Published: Nov. 10, 2023
An
efficient
route
for
the
copper(II)-catalyzed
synthesis
of
substituted
pyrazolines
from
readily
accessible
N-propargyl
hydrazones
has
been
reported
under
open
flask
conditions
via
intramolecular
C-N
bond
formation.
N-acyl
and
N-tosyl-substituted
have
prepared
in
moderate
to
excellent
yields.
Mechanistic
investigations
using
NMR,
high-resolution
mass
spectrometry
(HRMS),
Hammett
analyses
suggest
that
Cu(II)
catalyst
generally
acts
as
a
Lewis
acid
form
an
iminium-ion
intermediate
cyclization,
which
afforded
desired
upon
hydrolysis.
One
progesterone
receptor
antagonist
also
synthesized
utilizing
this
reaction
methodology.
Organic Chemistry Frontiers,
Journal Year:
2025,
Volume and Issue:
unknown
Published: Jan. 1, 2025
Enantioselective
synthesis
of
isoxazolines
bearing
allenes
by
palladium
catalyzed
carboetherification
alkenyl
oximes
with
propargylic
acetates.
DFT
calculations
carried
out
to
disclose
the
detailed
mechanism
and
origins
enantioselectivity.
Angewandte Chemie International Edition,
Journal Year:
2023,
Volume and Issue:
62(20)
Published: March 10, 2023
The
palladium-catalyzed
asymmetric
carboamination
reaction
is
one
of
the
most
significant
transformations
in
organic
chemistry.
Herein,
we
report
first
alleneamination
β,γ-unsaturated
hydrazones
with
propargylic
acetates.
This
protocol
enables
efficient
installation
various
multisubstituted
allene
groups
onto
dihydropyrazoles
good
yields
excellent
enantioselectivities.
chiral
sulfinamide
phosphine
ligand
Xu-5
exhibits
highly
stereoselective
control
this
protocol.
salient
features
include
readily
available
starting
materials,
a
broad
substrate
scope,
an
easy
scale-up,
mild
conditions
and
versatile
transformations.
Advanced Synthesis & Catalysis,
Journal Year:
2023,
Volume and Issue:
365(12), P. 1934 - 1969
Published: May 22, 2023
Abstract
2‐Pyrazolines
are
important
five‐membered
heterocycles,
containing
two
adjacent
nitrogen
atoms.
They
can
incorporate
various
functional
groups
and
possess
unique
biological
properties.
Moreover,
they
have
been
used
as
useful
building
blocks.
In
recent
years,
the
field
of
2‐pyrazoline
synthesis
has
experienced
enormous
progress.
Novel
strategies
developed,
many
studies
reporting
improvements
or
adaptations
existing
protocols
published,
giving
access
to
new
functionalizations,
unexplored
structures,
and/or
enantioselective
synthesis.
This
review
summarizes
progress
made
in
synthetic
methodologies
during
period
from
2012
2022.
The
functionalization
challenges
capabilities,
scopes
limitations
reactions,
substitution
patterns,
mechanisms
where
appropriate,
will
be
discussed.
Chemical Communications,
Journal Year:
2025,
Volume and Issue:
unknown
Published: Jan. 1, 2025
Herein,
we
reported
a
palladium-catalysed
alleneamination
of
γ,δ-unsaturated
hydrazones
with
propargylic
acetates,
which
provides
an
efficient
approach
for
the
synthesis
tetrahydropyridazine
bearing
allenes
in
moderate
to
good
yields.
Organic Letters,
Journal Year:
2023,
Volume and Issue:
25(25), P. 4682 - 4687
Published: June 19, 2023
A
highly
efficient
Pd-catalyzed
carboetherification
reaction
of
β,γ-unsaturated
ketoximes
with
propargylic
acetates
is
demonstrated.
This
method
provides
a
practical
protocol
for
accessing
the
incorporation
an
allene
moiety
into
3,5-disubstituted
and
3,5,5-trisubstituted
isoxazolines.
The
salient
features
this
transformation
include
broad
substrate
scope,
good
functional
group
tolerance,
easy
scale-up,
versatile
transformations,
applications
in
late-stage
modification
drugs.
Organic Chemistry Frontiers,
Journal Year:
2024,
Volume and Issue:
11(10), P. 2768 - 2773
Published: Jan. 1, 2024
Synthesis
of
isoxazolines
and
dihydrooxazines
bearing
an
alkyne
group
by
Pd-catalyzed
oxyalkynylation
alkenyl
oximes
with
alkynyl
bromides.
This
new
approach
has
a
broad
substrate
scope
good
functional
tolerance.
The Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
89(3), P. 1941 - 1955
Published: Jan. 23, 2024
A
highly
robust,
general,
and
practically
simple
palladium-catalyzed
domino
bicyclization
strategy
is
presented
to
synthesize
nitrogen-containing
bis-heterocycles
bearing
methylene
indole
motifs
from
alkyne-tethered
carbamoyl
chlorides
β,γ-
or
γ,δ-unsaturated
hydrazones.
The
salient
features
of
this
transformation
include
broad
substrate
scope,
good
functional
group
tolerance,
ease
for
scale-up,
convenient
conversion.
Angewandte Chemie,
Journal Year:
2023,
Volume and Issue:
135(20)
Published: March 10, 2023
Abstract
The
palladium‐catalyzed
asymmetric
carboamination
reaction
is
one
of
the
most
significant
transformations
in
organic
chemistry.
Herein,
we
report
first
alleneamination
β,γ
‐
unsaturated
hydrazones
with
propargylic
acetates.
This
protocol
enables
efficient
installation
various
multisubstituted
allene
groups
onto
dihydropyrazoles
good
yields
excellent
enantioselectivities.
chiral
sulfinamide
phosphine
ligand
Xu
5
exhibits
highly
stereoselective
control
this
protocol.
salient
features
include
readily
available
starting
materials,
a
broad
substrate
scope,
an
easy
scale‐up,
mild
conditions
and
versatile
transformations.
Asian Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
12(7)
Published: June 2, 2023
Abstract
Herein,
we
presented
a
novel
and
highly
efficient
strategy
for
the
synthesis
of
dihydropyrazoles
via
Pd‐catalyzed
carboamination
reaction
alkenyl
hydrazones
with
aryl
triflates.
The
simultaneous
formation
C−C
C−N
bonds
in
one
step
is
particularly
appealing.
This
methodology
provides
practical
avenue
diversely
substituted
good
yields.
Organic & Biomolecular Chemistry,
Journal Year:
2023,
Volume and Issue:
21(28), P. 5742 - 5746
Published: Jan. 1, 2023
Pd/Cu-catalyzed
cascade
Heck-type
reactions
of
alkenyl
halides
with
terminal
alkynes
have
been
developed.
This
research
provides
an
efficient
atom-economical
approach
to
access
a
variety
highly
substituted
pyrrolidines
in
moderate
good
yields.
protocol
features
readily
available
substrates,
broad
substrate
scope,
easy
scale-up,
high
selectivities
and
versatile
transformations.
