Photocatalytic Three-Component Reductive Coupling Synthesis of gem-Difluorohomoallyl Secondary Amines
Bingbing Feng,
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Meifang Tang,
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Rui Xiao
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et al.
The Journal of Organic Chemistry,
Journal Year:
2025,
Volume and Issue:
unknown
Published: Jan. 23, 2025
gem-Difluorohomoallyl
amines,
an
important
class
of
gem-difluoroalkenes,
are
prevalent
moieties
in
many
bioactive
compounds.
However,
limited
methods
suitable
for
the
synthesis
this
type
compound
containing
secondary
amines.
Here,
we
display
a
photocatalytic
multicomponent
protocol
gem-difluoroalkenes
which
makes
use
readily
available
materials:
arylamines,
alkyl
aldehydes,
and
α-trifluoromethyl
alkenes.
Moreover,
ketones
amines
also
substrates.
Preliminary
mechanistic
experiments
indicate
that
key
α-amino
radical
was
involved,
generated
from
reduction
situ-formed
imines
(or
iminium
ions)
by
reduced
photocatalyst.
Subsequent
addition
to
alkenes
β-F
elimination
deliver
desired
products.
Language: Английский
Nickel-Catalyzed Asymmetric Homobenzylic Hydroamidation of Aryl Alkenes to Access Chiral β-Arylamides
Xiang Lyu,
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Eunmi Jeon,
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Changhyeon Seo
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et al.
Journal of the American Chemical Society,
Journal Year:
2025,
Volume and Issue:
unknown
Published: Feb. 25, 2025
Herein,
we
introduce
a
Ni-catalyzed
asymmetric
homobenzylic
hydroamidation
reaction
that
efficiently
addresses
the
dual
challenges
of
achieving
regio-
and
enantioselectivity
in
synthesis
β-(hetero)arylethylamides.
By
employing
transposed
NiH
catalysis
approach,
this
method
facilitates
formation
key
chiral
nickel-amido
intermediates,
enabling
insertion
into
alkenes
to
produce
desired
β-arylamide
products
with
excellent
enantioselectivity.
The
exhibits
high
functional
group
tolerance
utilizes
readily
available
starting
materials
vinylarenes
react
dioxazolone
as
robust
amidating
source.
Notably,
approach
was
successfully
applied
pharmaceutical
compounds
natural
products,
such
Clobenzorex,
Direx,
Selegiline,
Sacubitril,
Cipargamin.
Language: Английский
α,α-Difluorinated Allylsulfones: gem-Difluoroethylenyl Reagents for Synthesis of Fluorinated Chiral α-Quaternary Amino Acids
Organic Letters,
Journal Year:
2025,
Volume and Issue:
unknown
Published: March 25, 2025
Among
numerous
fluorine-containing
molecules,
chiral
gem-difluoroethylenes
(C═CF2)
exhibited
unique
properties
in
agrochemicals,
pharmaceuticals,
and
materials
science.
However,
the
general
synthetic
methods
were
limited
to
functionalization/defluorination
of
trifluoromethylalkenes.
Here,
we
disclose
a
new
type
difluoroethylenyl
reagent,
α,α-difluoro
allylsulfones,
which
allows
highly
enantioselective
Cu-catalyzed
desulfonylative
SN2′
substitution
with
benzylideneamino
esters.
This
protocol
presents
novel
strategy
for
construction
diversified
α-quaternary
amino
acid
derivatives
containing
gem-difluoroethylene
moiety
excellent
results
(up
86%
yield,
generally
90–98%
ee).
The
ease
synthesis
applications
this
protocol,
transformations
products
revealed
potential
utility
chemistry.
Language: Английский
Photoredox-Catalyzed Alkylamination of Alkenes via Oxidative Radical-Polar Crossover and Site-Selective 1,5-Hydrogen Atom Transfer
Tianle Huang,
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Jianghong Liu,
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Zhen-Ye Wu
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et al.
Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(32), P. 6847 - 6852
Published: Aug. 7, 2024
We
reported
the
visible-light-mediated
photoredox-catalyzed
oxidative
radical-polar
crossover
and
1,5-hydrogen
atom
transfer
combined
site-selective
remote
C(sp
Language: Английский
Direct C–H difluoroallylation of α,β-unsaturated amides and aryl amides by rhodium catalysis
Wenqian Ding,
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Wenxiang Hu,
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Nanjun Chen
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et al.
Chemical Communications,
Journal Year:
2024,
Volume and Issue:
unknown
Published: Jan. 1, 2024
The
first
example
of
Rh-catalyzed
C(sp
2
)–H
difluoroallylation
α,β-unsaturated
amides
with
3-bromo-3,3-difluoropropene
has
been
developed
under
mild
conditions.
Language: Английский
Photoredox Catalyzed Reductive Trifluoromethylation of Imines via radical umpolung strategy
Hrishikesh Paul,
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Dibyangshu Das,
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SK Ariyan
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et al.
Chemical Communications,
Journal Year:
2024,
Volume and Issue:
unknown
Published: Jan. 1, 2024
A
photocatalyzed
radical-umpolung
strategy
is
developed
to
synthesize
trifluoromethylated
α-unnatural
amino
acids
and
amines.
This
method
involves
the
migration
of
an
N-centred
radical
through
aromatic
framework
construct
C–CF
3
bond.
Language: Английский
Decatungstate-Photocatalyzed Transformations of 2-Bromo-3,3,3-trifluoropropene for Selective Synthesis of Z/E-β-CF3-Enones
Xiao-Ya Yuan,
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Zhimin Lü,
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Xianqiang Huang
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et al.
Organic Letters,
Journal Year:
2024,
Volume and Issue:
unknown
Published: Dec. 2, 2024
Condition-controlled
switchable
and
divergent
transformations
of
cost-effective
2-bromo-3,3,3-trifluoropropene
(BTP)
aldehydes
were
realized
using
a
decatungstate
(TBADT)-photocatalyzed
strategy.
The
hydroacylated
products,
i.e.,
β,β-Br,CF
Language: Английский
Photocatalyzed cascade hydrogen atom transfer for the construction of α-CF3-1,4-diketones
Xiao-Ya Yuan,
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Jinping Zheng,
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Xinyu Ma
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et al.
Organic Chemistry Frontiers,
Journal Year:
2024,
Volume and Issue:
unknown
Published: Dec. 5, 2024
A
TBADT-photocatalyzed
cascade
hydrogen
atom
transfer
procedure
was
established
for
the
synthesis
of
α-CF
3
-1,4-diketones
from
aldehydes
and
2-bromo-3,3,3-trifluoro-1-propenes.
Language: Английский