The Journal of Organic Chemistry,
Journal Year:
2019,
Volume and Issue:
84(3), P. 1630 - 1639
Published: Jan. 4, 2019
A
catalyst
and
additive-free
annulation
of
2-pyridylacetates
ynals
under
molecular
oxygen
was
the
first
developed,
affording
3-acylated
indolizines
in
good
to
excellent
yields.
Molecular
used
as
source
carbonyl
atom
indolizines.
This
approach
compatible
with
a
wide
range
functional
groups,
especially
it
has
been
successfully
extended
unsaturated
double
bonds
triple
bonds,
which
were
difficult
prepare
by
previous
methods
single
step.
Angewandte Chemie International Edition,
Journal Year:
2017,
Volume and Issue:
56(16), P. 4540 - 4544
Published: March 22, 2017
Rhodium-catalyzed
C(sp2
)-H
functionalization
reactions
of
4-aryl-5-pyrazolones
followed
by
[3+2]
annulation
with
alkynes
provide
rapid
access
to
highly
enantioenriched
five-membered-ring
4-spiro-5-pyrazolones.
The
use
a
chiral
SCpRh
catalyst
enabled
the
synthesis
large
range
spiropyrazolones
all-carbon
quaternary
stereogenic
centers
in
up
99
%
yield
and
98
ee
from
readily
available
substrates.
Organic Letters,
Journal Year:
2017,
Volume and Issue:
19(13), P. 3410 - 3413
Published: June 12, 2017
Rh-catalyzed
C–H
activation
of
phenacyl
phosphoniums
in
coupling
with
α-diazocarbonyl
compounds
has
been
realized
the
assistance
a
mutifunctional
phosphonium
ylidic
directing
group,
providing
expedient
accesses
to
1-naphthols
and
isocoumarins.
Switchable
synthesis
isocoumarins
was
by
substrate
control,
where
these
transformations
were
enabled
initial
subsequent
intramolecular
Wittig
reaction
or
nucleophilic
C–O
formation.
Organic Letters,
Journal Year:
2018,
Volume and Issue:
20(8), P. 2477 - 2480
Published: April 3, 2018
A
novel
approach
for
the
synthesis
of
indolizines
from
2-(pyridin-2-yl)acetates,
ynals,
and
alcohols
or
thiols
has
been
developed.
This
MCR
(multicomponent
reaction)
that
proceeds
under
solvent-
metal-free
conditions
provided
a
straightforward
path
to
construct
indolizines.
Furthermore,
this
reaction
demonstrates
other
attractive
features
such
as
widely
available
starting
materials,
mild
conditions,
good
functional
group
tolerance,
high
efficiency.
Angewandte Chemie,
Journal Year:
2017,
Volume and Issue:
129(16), P. 4611 - 4615
Published: March 22, 2017
Abstract
Rhodium‐catalyzed
C(sp
2
)−H
functionalization
reactions
of
4‐aryl‐5‐pyrazolones
followed
by
[3+2]
annulation
with
alkynes
provide
rapid
access
to
highly
enantioenriched
five‐membered‐ring
4‐spiro‐5‐pyrazolones.
The
use
a
chiral
SCpRh
catalyst
enabled
the
synthesis
large
range
spiropyrazolones
all‐carbon
quaternary
stereogenic
centers
in
up
99
%
yield
and
98
ee
from
readily
available
substrates.
The Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
89(4), P. 2794 - 2799
Published: Jan. 31, 2024
A
Brønsted
acid
catalyzed
aza-Friedel–Crafts
reaction
of
indolizines
with
3-hydroxyisoindolinones
has
been
established,
which
constructs
isoindolinone
derivatives
bearing
a
tetrasubstituted
stereocenter
in
good
to
high
yields
and
enantioselectivities.
Notably,
this
strategy
provides
new
access
C1-functionalization
excellent
regioselectivities.
Moreover,
intriguing
C1-regioselective
transformation
was
induced
under
thermodynamic
control.
The Journal of Organic Chemistry,
Journal Year:
2017,
Volume and Issue:
82(18), P. 9291 - 9304
Published: Aug. 1, 2017
The
Cu-catalyzed
three-component
reaction
between
quinolines,
diazo
compounds,
and
alkenes
has
been
established
for
direct
construction
of
indolizine
derivatives
via
quinolinium
ylides.
This
methodology
is
distinguished
by
the
use
a
commercially
inexpensive
catalyst
readily
available
starting
materials,
wide
substrate
scope,
operational
simplicity.
Organic & Biomolecular Chemistry,
Journal Year:
2019,
Volume and Issue:
17(6), P. 1442 - 1454
Published: Jan. 1, 2019
A
general
method
for
the
synthesis
of
substituted
indolizines
by
copper(ii)
acetate-promoted
oxidative
[3
+
2]-annulation
α-fluoronitroalkenes
with
in
situ
generated
pyridinium
ylides
was
developed.
Application
acetate-2,6-lutidine
system
provides
efficient
access
to
various
1-fluoroindolizines
up
81%
yield.
Both
electron-rich
and
electron-deficient
nitroalkenes
as
well
different
isoquinolinium
salts
can
be
involved
reaction.
Moreover,
it
found
that
copper-mediated
annulation
is
applicable
other
α-substituted
(alkyl,
chloro,
ester)
giving
rise
corresponding
indolizines.
First
monofluorinated
[3,2,2]cyclazines
demonstrated
via
3-unsubstituted
fluoroindolizines
diethyl
acetylene
dicarboxylate.
Asian Journal of Organic Chemistry,
Journal Year:
2020,
Volume and Issue:
9(8), P. 1133 - 1143
Published: June 16, 2020
Abstract
Pyridinium
ylide
is
a
versatile
building
block
in
synthetic
organic
chemistry,
especially
the
synthesis
of
N
‐heterocycles.
In
this
minireview,
we
have
summarized
advances
[3+2]‐cycloaddition
catalytically
generated
pyridinium
for
indolizines
(since
1970s).
Accordingly,
discussed
article
situ
from
carbene
precursors
and
‐heteroarenes
under
catalytic
conditions,
including
photocatalysis/thermocatalysis,
metal‐catalysis.
The
metal‐catalyzed
version
main
focus,
which
classified
based
on
type
dipolarophiles,
alkyne
alkene,
each
class
further
subdivided
according
to
metal
catalysts
used
these
reactions.
analogous
vinyl
with
pyridines,
formation
other
or
different
‐heteroarenes,
been
also
included
herein
separately.
Organic Letters,
Journal Year:
2016,
Volume and Issue:
18(15), P. 3898 - 3901
Published: July 21, 2016
A
rhodium(III)-catalyzed
C–H/N–H
bond
functionalization
for
the
synthesis
of
1-aminoisoquinolines
from
aryl
amidines
and
α-MsO/TsO/Cl
ketones
was
achieved
under
mild
reaction
conditions.
Thus,
this
approach
provides
a
practical
method
site-selective
various
synthetically
valuable
isoquinolines
with
wide
functional
group
tolerance.
