Advanced Synthesis & Catalysis,
Journal Year:
2024,
Volume and Issue:
366(15), P. 3316 - 3324
Published: Aug. 6, 2024
Abstract
A
domino
reaction
comprising
four
consecutive
steps
based
on
the
strategy
of
isomerization
allylic
alcohols
was
developed.
This
base‐catalyzed
protocol
provided
an
approach
for
constructing
polysubstituted
quinolines
without
additional
additives.
wide
range
di‐
or
trisubstituted
γ‐
aminoaryl
bearing
alkyl
(hetero)aryl
substituents
were
transformed
to
a
structurally
diverse
quinolines.
The
utility
this
transformation
demonstrated
by
application
in
concise
synthesis
several
quinoline
derivatives,
including
natural
products
and
pharmacological
agents.
Preliminary
mechanistic
experiments
suggest
that
alcohol
proceeds
via
intramolecular
1,3‐hydrogen
shift
whereas
aromatization
dihydroquinoline
intermediate
two
possible
pathways
exist:
acceptorless
dehydrogenation
transfer
hydrogenation.
The Journal of Organic Chemistry,
Journal Year:
2021,
Volume and Issue:
86(23), P. 16641 - 16651
Published: Nov. 11, 2021
An
asymmetric
transfer
hydrogenation
(ATH)
of
quinolines
in
water
or
biphasic
systems
was
developed.
This
ATH
reaction
proceeds
smoothly
without
the
need
for
inert
atmosphere
protection
presence
a
water-soluble
iridium
catalyst,
which
bears
an
easily
available
aminobenzimidazole
ligand.
system
can
work
at
catalyst
loading
0.001
mol
%
(S/C
=
100
000,
turnover
number
(TON)
up
to
33
000)
under
mild
conditions.
The
frequency
(TOF)
value
reach
as
high
90
000
h–1.
A
variety
quinoline
and
N-heteroaryl
compounds
are
transformed
into
desired
products
yield
99%
enantiomeric
excess
(ee).
Inorganic Chemistry Frontiers,
Journal Year:
2021,
Volume and Issue:
8(24), P. 5214 - 5224
Published: Jan. 1, 2021
Two
isostructural
heterometallic
dodecanuclear
nanoclusters
[Dy
4
Co
8
(μ
3
-OH)
(L)
(OAc)
(H
2
O)
]·3EtOH·3CH
CN·H
O
(1)
and
Ni
]·3.5EtOH·0.5CH
CN·5H
(2)
with
different
assembly
mechanisms
are
presented
here.
Advanced Synthesis & Catalysis,
Journal Year:
2023,
Volume and Issue:
365(8), P. 1275 - 1286
Published: March 29, 2023
Abstract
The
RuPHOX‐Ru
catalyzed
asymmetric
hydrogenation
of
diaryl
ketones
has
been
established,
providing
the
corresponding
chiral
methanols
in
up
to
99%
yield
and
ee.
protocol
could
be
performed
on
a
gram‐scale
with
relatively
low
catalyst
loading
(2000
S/C)
resulting
products
allow
for
several
useful
transformations,
particular
synthesis
drugs,
such
as,
(
S
)‐Orphenadrine
)‐Neobenodine.
Deuterium
labeling
control
experiments
revealed
that
RuPHOX‐Ru‐catalyzed
is
fully
subject
H
2
as
sole
hydrogen
source.
magnified
image
Journal of Catalysis,
Journal Year:
2021,
Volume and Issue:
404, P. 451 - 461
Published: Oct. 25, 2021
We
report
on
an
operationally
simple
catalytic
method
for
the
tungsten-catalyzed
hydrogenation
of
quinolines
through
use
easily
handled
and
self-contained
precursor
[WCl(η5-Cp)(CO)3].
This
half
sandwich
complex
is
indefinitely
storable
bench
in
screw-capped
bottles
or
stoppered
flasks
can,
if
required,
be
prepared
a
multi-gram
scale
while
actual
transformations
were
performed
presence
Lewis
acid
order
to
achieve
both
decent
substrate
conversions
product
yields.
The
described
represents
facile
atom-efficient
access
variety
1,2,3,4-tetrahydroquinolines
that
circumvents
cost-intensive
oxygen-sensitive
phosphine
ligands
as
well
auxiliary
hydride
reagents.
Chemical Science,
Journal Year:
2021,
Volume and Issue:
13(4), P. 985 - 995
Published: Dec. 20, 2021
The
chiral
ruthenium(ii)bis-SINpEt
complex
is
a
versatile
and
powerful
catalyst
for
the
hydrogenation
of
broad
range
heteroarenes.
This
study
aims
to
provide
understanding
active
form
this
privileged
as
well
reaction
mechanism,
identify
factors
which
control
enantioselectivity.
To
end
we
used
computational
methods
Chemical Science,
Journal Year:
2023,
Volume and Issue:
14(18), P. 4888 - 4892
Published: Jan. 1, 2023
The
highly
efficient
Rh/ZhaoPhos-catalysed
asymmetric
hydrogenation
of
γ-butenolides
and
γ-hydroxybutenolides
was
successfully
developed.
This
protocol
provides
an
practical
approach
to
the
synthesis
various
chiral
γ-butyrolactones,
which
are
synthetically
valuable
building
blocks
diverse
natural
products
therapeutic
substances,
with
excellent
results
(up
>99%
conversion
99%
ee).
Further
follow-up
transformations
have
been
revealed
accomplish
creative
synthetic
routes
for
several
enantiomerically
enriched
drugs
via
this
catalytic
methodology.
Advanced Synthesis & Catalysis,
Journal Year:
2023,
Volume and Issue:
365(7), P. 1027 - 1035
Published: March 16, 2023
Abstract
Rh(III)‐catalyzed
chelation‐assisted
C8‐selective
C−H
alkenylation
and
alkylation
of
1,2,3,4‐tretrahydroquinolines
with
styrenes
allylic
alcohols
have
been
realized.
The
cationic
Rh(III)
catalytic
system
in
combination
a
amount
copper
acetate
uses
oxygen
as
the
terminal
oxidant
catalyzes
stereoselective
C8‐alkenylation
1,2,3,4‐tetrahydroquinolines
to
give
corresponding
products
56–93%
yields
wide
substrate
scope
broad
functional
group
compatibility.
reaction
can
be
scaled
up.
Moreover,
this
protocol
extended
C8‐alkylation
alcohols,
providing
access
various
8‐(3‐oxoalkyl)‐1,2,3,4‐tetrahydroquinolines
77–90%
yields.
selection
N‐directing
is
essential
for
catalysis,
readily
installable
removable
N‐(2‐pyrimidyl)
proves
optimal
choice.
Preliminary
mechanistic
studies
are
performed
gain
insights
into
mechanism.
magnified
image
