Journal of the American Chemical Society,
Год журнала:
2024,
Номер
146(35), С. 24663 - 24669
Опубликована: Авг. 20, 2024
Chiral
borane–catalyzed
reactions
have
recently
emerged
as
a
powerful
tool
for
the
enantioselective
production
of
chiral
scaffolds.
In
this
study,
we
demonstrated
first
time
that
bisborane
catalyst
can
be
used
α-functionalization
2-alkylazaarenes;
specifically,
accomplished
unprecedented
highly
α-alkylation
unactivated
2-alkylbenzoxazoles
with
electron-deficient
olefins.
The
strong
Lewis
acidity
and
steric
bulk
were
essential
to
observed
reactivity
selectivity.
Organic Chemistry Frontiers,
Год журнала:
2020,
Номер
7(20), С. 3312 - 3342
Опубликована: Янв. 1, 2020
This
review
describes
recent
developments
in
enantioselective
imine
reduction,
including
related
substrates
which
a
CN
bond
is
the
target
for
and
in
situ
methods.
Angewandte Chemie International Edition,
Год журнала:
2019,
Номер
58(33), С. 11505 - 11512
Опубликована: Июнь 13, 2019
Abstract
In
order
to
effectively
synthesize
chiral
α‐amino
aldehydes,
which
have
a
wide
range
of
potential
applications
in
organic
synthesis
and
medicinal
chemistry,
highly
chemo‐
enantioselective
hydrogenation
α‐formyl
enamides
has
been
developed,
catalyzed
by
rhodium
complex
P‐stereogenic
bisphosphine
ligand.
Under
different
hydrogen
pressures,
the
α‐amido
aldehydes
β‐amido
alcohols
were
obtained
high
yields
(97–99
%)
with
excellent
enantioselectivities
(up
>99.9
%
ee
).
The
can
be
carried
out
on
gram
scale
substrate/catalyst
ratio
20
000
S/C),
hydrogenated
products
further
converted
into
several
important
products.
Computations
catalytic
cycle
gave
clear
description
for
R
/
S
pathways,
provided
reasonable
explanation
enantioselectivity,
revealed
other
specific
features.
Chemical Society Reviews,
Год журнала:
2023,
Номер
52(24), С. 8580 - 8598
Опубликована: Янв. 1, 2023
This
review
provides
an
overview
of
the
important
progress
in
FLP-catalyzed
asymmetric
reactions
made
over
past
15
years,
and
both
merits
limitations
FLP-catalysis
have
been
highlighted.
Advanced Materials,
Год журнала:
2024,
Номер
36(41)
Опубликована: Сен. 2, 2024
Abstract
Earth‐abundant
Co
X‐ides
are
emerging
as
promising
catalysts
for
the
electrocatalytic
hydrogenation
of
quinoline
(ECHQ),
yet
challenging
due
to
limited
fundamental
understanding
ECHQ
mechanism
on
X‐ides.
This
work
identifies
catalytic
performance
differences
in
and
provides
significant
insights
into
ECHQ.
Among
selected
X‐ides,
3
O
4
presents
best
with
a
high
conversion
98.2%
100%
selectivity
at
ambient
conditions.
The
sites
present
higher
proportion
2‐coordinated
hydrogen‐bonded
water
interface
than
other
low
negative
potential,
which
enhances
kinetics
subsequent
dissociation
produce
H*.
An
ideal
1,4/2,3‐H*
addition
pathway
surface
spontaneous
desorption
1,2,3,4‐tetrahydroquinoline
is
demonstrated
through
operando
tracing
theoretical
calculations.
In
comparison,
9
S
8
display
lowest
thermodynamic
barrier
H*
formation
step,
suppresses
hydrogenation;
while
Co(OH)F
CoP
undergo
1,2,3,4‐
4,3/1,2‐H*
respectively
barriers
thus
quinoline.
Moreover,
wide
substrate
scope
allows
excellent
derivatives
N
‐heterocyclic
substrates.
Journal of the American Chemical Society,
Год журнала:
2024,
Номер
unknown
Опубликована: Дек. 11, 2024
The
homogeneous
catalytic
hydrogenation
of
benzo-fused
heteroarenes
generally
provides
partially
hydrogenated
products
wherein
the
heteroaryl
ring
is
preferentially
reduced,
such
as
quinoline
hydrogenation,
leading
to
1,2,3,4-tetrahydroquinoline.
Herein,
we
report
a
carbocycle-selective
fused
Advanced Synthesis & Catalysis,
Год журнала:
2020,
Номер
362(19), С. 4119 - 4129
Опубликована: Июль 22, 2020
Abstract
A
generalized,
simple
and
efficient
transfer
hydrogenation
of
unsaturated
bonds
has
been
developed
using
HBPin
various
proton
reagents
as
hydrogen
sources.
The
substrates,
including
alkenes,
alkynes,
aromatic
heterocycles,
aldehydes,
ketones,
imines,
azo,
nitro,
epoxy
nitrile
compounds,
are
all
applied
to
this
catalytic
system.
Various
groups,
which
cannot
survive
under
the
Pd/C/H
2
combination,
tolerated.
activity
reactants
was
studied
trends
follows:
styrene>diphenylmethanimine>benzaldehyde>azobenzene>nitrobenzene>quinoline>acetophenone>benzonitrile
.
Substrates
bearing
two
or
more
different
were
also
investigated
occurred
with
excellent
chemoselectivity.
Nano‐palladium
catalyst
in
situ
generated
from
Pd(OAc)
extremely
improved
TH
efficiency.
Furthermore,
chemoselective
anti‐Markovnikov
hydrodeuteration
terminal
olefins
achieved
D
O
via
HD
generation
discrimination.
magnified
image
Angewandte Chemie International Edition,
Год журнала:
2021,
Номер
60(31), С. 17185 - 17190
Опубликована: Май 26, 2021
Abstract
Herein,
we
present
a
mild
and
efficient
method
for
synthesizing
enantioenriched
tetrahydroquinoline‐fused
cyclobutenes
through
cascade
reaction
between
1,2‐dihydroquinolines
alkynones
with
catalysis
by
chiral
spiro‐bicyclic
bisboranes.
The
bisboranes
served
two
functions:
first
they
catalyzed
hydride
transfer
to
convert
the
1,2‐dihydroquinoline
substrate
1,4‐dihydroquinoline,
then
activated
alkynone
an
enantioselective
[2+2]
cycloaddition
1,4‐dihydroquinoline
generated
in
situ.
Journal of the American Chemical Society,
Год журнала:
2021,
Номер
143(8), С. 3054 - 3059
Опубликована: Фев. 11, 2021
Herein,
we
report
that,
by
using
chiral
bicyclic
bisborane
catalysts,
have
achieved
the
first
highly
regio-,
diastereo-,
and
enantioselective
direct
asymmetric
vinylogous
Mannich
reactions
of
acyclic
α,β-unsaturated
ketones.
The
strong
Lewis
acidity
steric
bulk
catalysts
were
essential
for
observed
high
yields
selectivities.
ACS Catalysis,
Год журнала:
2019,
Номер
9(6), С. 5439 - 5444
Опубликована: Май 3, 2019
Recent
progress
on
the
triarylborane
(BAr3)-catalyzed
reductive
N-alkylation
of
amines
is
briefly
summarized
in
this
Perspective.
The
highlighted
examples
are
divided
into
two
main
classes,
that
is,
B(C6F5)3-catalyzed
hydroamination
alkynes
and
subsequent
catalytic
hydrogenation,
as
well
BAr3-catalyzed
carbonyl
compounds
such
aldehydes,
ketones,
carboxylic
acids
presence
hydrosilanes
or
molecular
hydrogen.
Key
aspects
several
systems
emphasized
order
to
discuss
reaction
mechanisms,
substrate
scope,
practical
applications
for
preparation
medicinal
compounds,
identification
remaining
challenges
area.