Advanced Synthesis & Catalysis,
Journal Year:
2023,
Volume and Issue:
365(24), P. 4544 - 4549
Published: Nov. 22, 2023
Abstract
The
air
mediated
radical
alkylation
of
cyclic
aldimines
via
autoxidation
alkylboronic
acids
has
been
realized
under
mild
reaction
conditions.
By
simply
heating
with
acid
using
as
sole
oxidant,
this
protocol
provides
a
catalyst‐free
access
to
variety
alkylated
21–91%
yields.
Preliminary
mechanistic
studies
suggest
that
pathway
might
be
involved
in
the
reaction.
Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(7), P. 1472 - 1477
Published: Feb. 13, 2024
A
highly
efficient
enantioselective
[4
+
2]
cycloaddition
of
2-amino-β-nitrostyrenes
with
cyclic
N-sulfonyl
ketimines
has
been
developed.
This
reaction
utilizes
an
organocatalytic
approach,
employing
a
multiple-hydrogen-bonding
bifunctional
squaramide-based
catalyst.
The
process
allows
for
the
precise
synthesis
chiral
polycyclic
benzosultams,
showcasing
intricate
structures
that
incorporate
quaternary
centers.
Noteworthy
outcomes
this
method
include
high
yields
excellent
enantioselectivities
and
diastereoselectivities
(up
to
97%
yield,
96%
ee,
>20:1
dr).
Chinese Journal of Chemistry,
Journal Year:
2023,
Volume and Issue:
42(8), P. 829 - 834
Published: Dec. 8, 2023
Comprehensive
Summary
The
Pd‐catalyzed
dipolar
cycloaddition
represents
a
significant
synthetic
strategy
for
the
construction
of
useful
heterocyclic
compounds.
This
study
developed
[4+2]
and
[6+2]
reactions
benzo[
d
]isothiazole
1,1‐dioxides
(BDs)
leading
to
synthesis
BD‐fused
1,3‐oxazinane
1,3‐oxazocane
derivatives,
respectively.
In
particular,
1,3‐oxazinanes
demonstrated
regio‐
enantioselective
characteristics,
resulting
in
products
with
good
yields,
enantioselectivity
regioselectivity
(if
applicable).
Furthermore,
reaction
this
work
represented
first
medium‐sized
ring
compounds
based
on
BDs.
Organic Letters,
Journal Year:
2025,
Volume and Issue:
unknown
Published: March 25, 2025
A
highly
efficient
enantioselective
Michael
addition
of
cyclic
N-sulfonylimines
with
nitroalkenes
has
been
developed,
utilizing
a
bifunctional
squaramide
catalyst.
This
approach
achieves
remarkable
results,
delivering
products
high
yields
and
outstanding
stereoselectivities,
reaching
up
to
97%
yield,
>20:1
dr,
>99%
ee.
Furthermore,
an
asymmetric
tandem
reaction
2-nitroallylic
acetates
established.
innovative
methodology
involves
Michael/intramolecular
aza-Michael
cascade,
leading
the
formation
enantioenriched
benzosultam-fused
tricyclic
compounds
excellent
stereoselectivities
(up
dr
ee).
New Journal of Chemistry,
Journal Year:
2024,
Volume and Issue:
48(32), P. 14163 - 14169
Published: Jan. 1, 2024
Efficient
access
to
α-carbolines
was
achieved
via
a
domino
reaction
between
iminoindoles
and
arylidene
malononitriles
using
DABCO/NaHCO
3
as
cooperative
basic
system.
The
synthesized
scaffolds
display
blue
emissions
with
good
quantum
yields.
The Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
89(24), P. 18337 - 18343
Published: Dec. 9, 2024
A
cerium-catalyzed
C–H
alkylation
of
N-sulfonyl
ketimines
with
low-cost
and
readily
available
alkanes
as
alkyl
sources
was
developed.
This
transformation
proceeded
through
the
synergy
photoinitiated
ligand-to-metal
charge
transfer
(LMCT)
using
a
chlorine
radical
an
HAT
reagent
air
green
oxidant.
series
alkylated
were
synthesized
moderate
to
good
yields
in
highly
atom-economic
manner
under
chemical
oxidant-free
conditions.
Organic & Biomolecular Chemistry,
Journal Year:
2021,
Volume and Issue:
20(2), P. 352 - 357
Published: Dec. 11, 2021
An
efficient
DABCO/Cu(OAc)
2
promoted
one-pot
access
to
pharmacologically
exciting
highly
substituted
6-hydroxyaryl-2-aminonicotinonitriles
in
good
high
yields
is
reported.
Organic & Biomolecular Chemistry,
Journal Year:
2022,
Volume and Issue:
20(34), P. 6759 - 6765
Published: Jan. 1, 2022
A
remarkable
metal-oxidant-solvent-
and
base-free
domino
route
for
regioselective
access
to
a
wide
range
of
2,4-di-
2,3,4/6-trisubstituted
pyridines
including
carbo-
heterocyclic
fused
is
reported.
This
[3C
+
2C
1N]
cyclization
reaction
occurs
between
3-chloropropiophenones
(3C
units),
enolizable
acyclic/cyclic
ketones
(2C
sources)
NH4OAc
as
robust
N
source
under
neat
conditions
an
open
atmosphere,
producing
new
C=C
C=N-C
bonds
in
highly
chemo-
manners.
Interestingly,
this
eco-friendly
method
has
many
positive
features:
excellent
functional
group
tolerance,
broad
substrate
scope,
good
regioselectivities,
promising
yields,
no-unwanted
products,
neutral
appropriateness
large-scale
synthesis.
Mechanism
studies
reveal
that
the
situ
generated
β-amino
ketone
from
3-chloropropiophenone
ammonium
salt
undergoes
C=N
bond
formation
with
followed
by
intramolecular
process
(C=C
bond),
which
are
decisive
steps
pyridine
Asian Journal of Organic Chemistry,
Journal Year:
2022,
Volume and Issue:
11(12)
Published: Nov. 1, 2022
Abstract
The
β‐Csp
3
−H
functionalization
of
N‐sulfonyl
ketimines
with
2‐(2‐enynl)pyridines/quinolines
via
a
cooperative
Ag(I)‐/organobase‐catalyzed
5‐
endo‐dig
cyclization‐addition
reaction
is
reported.
This
successive
C−N/C−C
bond‐making
provides
simple
and
atom‐economical
technique
for
granting
diverse
set
1,3‐disubstituted
indolizines/pyrrolo[1,2‐
]quinolines
possessing
synthetically
resourceful
ketimine
moiety.
Moreover,
our
designed
strategy
applies
to
broad
substrates
allows
various
functionalities.
Furthermore,
this
has
many
imperative
synthetic
points
such
as
mild
conditions,
low
catalyst
loading,
acceptable
chemical
yields
highly
diastereoselective
(up
≤93
:
7
dr).
moiety
indolizine
was
easily
transmuted
into
the
reputed
classes
coumarin
benzofuran
derivatives.
Green Synthesis and Catalysis,
Journal Year:
2023,
Volume and Issue:
unknown
Published: Oct. 1, 2023
We
first
describe
a
photoinduced
decatungstate-catalyzed
direct
coupling
of
cycloalkanes
and
cyclic
aldimines.
The
desired
products
were
generated
in
moderate
to
good
yields
with
wide
substrate
scope
under
mild
reaction
conditions.
mechanistic
study
revealed
radical
process.
In
addition,
the
usefulness
organic
synthesis
was
proved
by
scale-up
as
well
late-stage
modification
drug-like
molecules.