Advanced Synthesis & Catalysis,
Journal Year:
2019,
Volume and Issue:
361(18), P. 4255 - 4277
Published: July 6, 2019
Abstract
A
mild,
efficient,
and
stable
binaphthyl‐stabilized
palladium
nanoparticles
(Pd−BNP)
catalyzed
(
sp
3
)C−H
reaction
of
2‐alkylazaarenes
with
activated
carbonyl
compounds
was
developed.
Various
such
as
α‐keto
amide,
isatin,
1,2‐diketone,
ester,
trifluoromethyl
ketone,
phenylglyoxal
derivatives
were
examined
most
the
underwent
smoothly
to
provide
corresponding
products
in
moderate
excellent
yields.
Moreover,
chemoselective
reactions
amides
presence
simple
ketones
achieved.
Also,
model
extended
a
gram‐scale
synthesis
some
utilized
for
derivatization
form
N
‐oxides,
acryl
1,2‐diol,
respectively.
The
major
advantages
protocol
are
neutral
conditions,
no
additional
requirement
external
ligand,
successful
reusability
Pd−BNP
catalyst
up
five
cycles
without
losing
its
activity
yield.
Hg‐poisoning
hot
filtration
tests
confirmed
heterogeneity
catalyst.
magnified
image
Chemistry - A European Journal,
Journal Year:
2019,
Volume and Issue:
25(53), P. 12431 - 12438
Published: July 18, 2019
A
bifunctional
amine/squaramide
catalyst
promoted
direct
aldol
addition
of
an
hydantoin
surrogate
to
pyridine
2-carbaldehyde
N-oxides
afford
adducts
bearing
two
vicinal
tertiary/quaternary
carbons
in
high
diastereo-
and
enantioselectivity
(d.r.
up
>20:1;
ee
98
%)
is
reported.
Acid
hydrolysis
followed
by
reduction
the
N-oxide
group
yields
enantiopure
carbinol-tethered
quaternary
hydantoin-azaarene
conjugates
with
densely
functionalized
skeletons.
DFT
studies
potential
energy
surface
(B3LYP/6-31+G(d)+CPCM
(dichloromethane))
reaction
correlate
activity
different
catalysts
support
intramolecular
hydrogen-bond-assisted
activation
squaramide
moiety
transition
state
catalytic
reaction.
Advanced Synthesis & Catalysis,
Journal Year:
2020,
Volume and Issue:
362(15), P. 3142 - 3147
Published: March 25, 2020
Abstract
The
enantioselective
synthesis
of
chiral
azaarenes
by
rhodium‐catalyzed
asymmetric
conjugate
addition
organoboronic
acids
to
carbonyl‐activated
alkenyl
was
reported.
Diverse
were
produced
in
up
99%
yield
and
with
ee
(>60
examples).
Catalytic
syntheses
dexchlorpheniramine
dexbrompheniramine
realized
using
the
developed
method.
magnified
image
Organic & Biomolecular Chemistry,
Journal Year:
2020,
Volume and Issue:
18(39), P. 7814 - 7817
Published: Jan. 1, 2020
A
chiral
ureate
as
a
strong
Brønsted
base
catalyst
enabled
an
efficient
synthesis
of
1,2-diphosphinoalkane
derivatives
through
catalytic
enantioselective
hydrophosphinylation
1-alkenylphosphine
oxides.
Angewandte Chemie,
Journal Year:
2018,
Volume and Issue:
130(35), P. 11544 - 11547
Published: June 29, 2018
Abstract
The
direct
enantioselective
synthesis
of
chiral
azaheteroaryl
ethylamines
from
vinyl‐substituted
N‐heterocycles
and
anilines
is
reported.
A
phosphoric
acid
(CPA)
catalyst
promotes
dearomatizing
aza‐Michael
addition
to
give
a
prochiral
exocyclic
aryl
enamine,
which
undergoes
asymmetric
protonation
upon
rearomatization.
reaction
accommodates
broad
range
N‐heterocycles,
nucleophiles,
substituents
on
the
centre,
generating
products
in
high
enantioselectivity.
DFT
studies
support
facile
nucleophilic
based
catalyst‐induced
LUMO
lowering,
with
site‐selective,
rate‐limiting,
intramolecular
proton
transfer
ion‐paired
intermediate.
Advanced Synthesis & Catalysis,
Journal Year:
2019,
Volume and Issue:
361(18), P. 4255 - 4277
Published: July 6, 2019
Abstract
A
mild,
efficient,
and
stable
binaphthyl‐stabilized
palladium
nanoparticles
(Pd−BNP)
catalyzed
(
sp
3
)C−H
reaction
of
2‐alkylazaarenes
with
activated
carbonyl
compounds
was
developed.
Various
such
as
α‐keto
amide,
isatin,
1,2‐diketone,
ester,
trifluoromethyl
ketone,
phenylglyoxal
derivatives
were
examined
most
the
underwent
smoothly
to
provide
corresponding
products
in
moderate
excellent
yields.
Moreover,
chemoselective
reactions
amides
presence
simple
ketones
achieved.
Also,
model
extended
a
gram‐scale
synthesis
some
utilized
for
derivatization
form
N
‐oxides,
acryl
1,2‐diol,
respectively.
The
major
advantages
protocol
are
neutral
conditions,
no
additional
requirement
external
ligand,
successful
reusability
Pd−BNP
catalyst
up
five
cycles
without
losing
its
activity
yield.
Hg‐poisoning
hot
filtration
tests
confirmed
heterogeneity
catalyst.
magnified
image
