Enantioselective Copper-Catalyzed Three-Component Cascade Boronation–Dearomatization Reaction: Synthesis of Chiral Boron-Containing 1,4-Dihydropyridines
Fazhou Yang,
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Yujie Dong,
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Jinbao Wang
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et al.
Organic Letters,
Journal Year:
2025,
Volume and Issue:
unknown
Published: Jan. 10, 2025
A
three-component
cascade
boronation–dearomatization
reaction
of
alkenes,
a
diboron
compound,
and
pyridinium
salt
is
diclosed,
affording
chiral
boron-containing
1,4-dihyropyridines
in
high
yields
(≤98%)
diastereoselectivity
(≤10:1
dr),
along
with
excellent
enantioselectivity
(typically
>99%
ee).
The
catalytic
system
performs
efficiently
at
low
catalyst
loadings
(1
mol
%)
was
tested
>50
examples,
including
some
biologically
active
molecules.
Language: Английский
Nickel catalyzed C-N coupling of haloarenes with B2N4 reagents
Qianqian Chang,
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Qini Li,
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Yi-Hui Deng
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et al.
Nature Communications,
Journal Year:
2025,
Volume and Issue:
16(1)
Published: April 3, 2025
Language: Английский
Metallaphotoredox-Catalyzed Three-Component Asymmetric Cross-Electrophile Coupling for Chiral Boronate Synthesis
Xiaofang Li,
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Yuntong Hu,
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Zhonghou Huang
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et al.
ACS Catalysis,
Journal Year:
2024,
Volume and Issue:
14(20), P. 15790 - 15798
Published: Oct. 10, 2024
Here,
we
report
a
photoredox
and
nickel-catalyzed
cross-electrophile
coupling
strategy
for
the
asymmetric
three-component
1,2-alkylarylation
of
vinyl
boronates
with
(hetero)aryl
bromides
(2°,
3°)-alkyl
redox-active
esters
in
presence
Hantzsch
ester.
With
fluorinated
pyridyl-substituted
chiral
biimidazoline
ligand,
this
reaction
enables
straightforward
access
to
wide
variety
synthetically
valuable
α-aryl
from
readily
available
starting
materials.
This
features
mild
conditions,
broad
substrate
generality,
good
functional
group
tolerance
proceeds
without
using
metal
reductants
or
alkyl
halides.
Furthermore,
alkenyl
halides
other
electron-deficient
alkenes
such
as
acrylates
phosphonates
can
be
applied
successfully.
Preliminary
mechanistic
studies
shed
light
on
potential
pathways
roles
organic
amines.
Language: Английский
Enantioselective Borylative Functionalization of Internal Alkenes: A Platform for Constructing Vicinal Stereocenters†
Chinese Journal of Chemistry,
Journal Year:
2024,
Volume and Issue:
42(24), P. 3588 - 3604
Published: Nov. 1, 2024
Comprehensive
Summary
Vicinal
stereogenic
centers
are
ubiquitous
structural
scaffolds
in
both
natural
products
and
synthetic
compounds,
yet
their
enantioselective
construction
remains
a
significant
challenge
organic
synthesis.
Organoboron
compounds
of
paramount
importance
chemistry
due
to
ability
undergo
facile
transformations,
yielding
diverse
essential
chemical
bonds
such
as
carbon‐carbon,
carbon‐oxygen,
carbon‐nitrogen,
carbon‐halogen
bonds.
Transition‐metal‐catalyzed
asymmetric
borylative
functionalizations
internal
alkenes
offer
promising
strategy
for
the
installation
two
adjacent
chiral
across
carbon‐carbon
By
leveraging
versatile
transformations
newly
introduced
boryl
unit,
this
approach
holds
great
potential
expanding
diversity
vicinal
scaffolds.
In
concise
review,
we
aim
highlight
recent
advancements
transition‐metal‐catalyzed
alkenes,
underscore
utility
constructing
centers,
discuss
unsolved
challenges
future
directions
field.
Key
Scientists
Language: Английский
Coordination-Assisted Ni-Catalyzed Regio- and Enantioselective 1,2-Borylalkylation of Unactivated Alkenes
Yuqin Zhu,
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Zhetai Feng,
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Wenyi Li
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et al.
Organic Letters,
Journal Year:
2024,
Volume and Issue:
unknown
Published: Dec. 4, 2024
Herein
we
successfully
utilize
various
directing
groups
to
achieve
a
ligand-enabled
nickel-catalyzed
1,2-borylalkylation
of
unactivated
alkenes.
A
β-amino
alcohol
was
employed
as
the
ligand
for
non-asymmetric
alkenes,
while
bulky
chiral
diamine
used
asymmetric
allyl
amides.
Language: Английский