Merging Photoinduced Electron Transfer with Hydrogen Atom Transfer: Formal β-C(sp3)–H Pyridination of Carbonyls
Jian Li,
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Jun Xu,
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Binbin Chen
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et al.
The Journal of Organic Chemistry,
Journal Year:
2025,
Volume and Issue:
unknown
Published: Jan. 9, 2025
In
this
study,
a
novel
approach
that
combines
photoinduced
electron
transfer
(ET)
with
hydrogen
atom
(HAT)
has
been
introduced
for
the
selective
β-C(sp3)–H
pyridination
of
carbonyl
compounds.
This
method
is
notable
its
absence
transition
metals
and
ability
to
function
under
benign
reaction
conditions,
resulting
in
range
pyridinated
derivatives
consistently
moderate
good
yields.
The
significance
technique
further
underscored
by
potential
late-stage
functionalization
pharmaceutically
significant
molecules.
Mechanistic
investigations
confirmed
proceeds
via
radical-mediated
pathway.
Language: Английский
1,2-Acylphosphinylation of Styrenes to Access β-Aryl-γ-ketophosphine Oxides by Irradiation-Induced Radical Relay
Dengyu Yin,
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Lishuai Lu,
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Yandong Dou
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et al.
The Journal of Organic Chemistry,
Journal Year:
2025,
Volume and Issue:
unknown
Published: March 11, 2025
An
acylphosphinylation
reaction
has
been
devised
for
the
synthesis
of
β-aryl-γ-ketophosphine
oxides,
employing
styrenes
and
acyl
azolium
salts
through
an
irradiation-induced
radical
relay
mechanism.
This
method
effectively
constructs
C–C
C–P
bonds
while
demonstrating
excellent
functional
group
tolerance.
Mechanistic
studies
revealed
that
a
radical-addition–coupling–elimination
cascade
process
was
involved
in
this
reaction.
Language: Английский
Direct Alkene Functionalization via Photocatalytic Hydrogen Atom Transfer from C(sp3)–H Compounds: A Route to Pharmaceutically Important Molecules
Hangqian Fan,
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Yuxin Fang,
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Jingbo Yu
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et al.
Chemical Communications,
Journal Year:
2024,
Volume and Issue:
unknown
Published: Jan. 1, 2024
Direct
functionalization
of
alkenes
with
C(sp
Language: Английский
Light-Driven Formate-Salts-Induced Cleavage of Oxidized Lignin Model Compounds
Siqi Xie,
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Yingjun Lan,
No information about this author
Bin Liu
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et al.
Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(39), P. 8249 - 8253
Published: Sept. 24, 2024
We
report
a
light-induced
cleavage
of
oxidized
lignin
model
compounds
utilizing
formate
salts.
For
containing
an
aliphatic
hydroxyl
(γ-OH)
group,
the
employment
hydrogen
atom
transfer
(HAT)
catalyst
was
crucial
to
preserving
efficacy
fragmentation
reaction.
Furthermore,
we
successfully
converted
trimeric
compound
into
desired
products
with
moderate
yields.
Language: Английский
Cu‐Catalyzed Coupling of Sulfonyl Chlorides with Alkenes: Synthesis of Dienyl Sulfones and β‐Chlorosulfones
European Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
unknown
Published: Oct. 14, 2024
Abstract
This
work
reports
a
Cu‐catalyzed
coupling
technique
for
synthesizing
(
E
)‐dienyl
sulfones
and
β‐chlorosulfones
from
1‐arylbutadienes
styrenes,
respectively.
By
employing
easily
available
inexpensive
reagents,
this
method
enables
the
synthesis
of
diverse
array
dienyl
with
excellent
functional
group
tolerance
under
base‐
oxidant‐free
conditions.
It
also
proves
versatile
late‐stage
functionalization
drug
molecules
scale‐up
reactions.
The
showcases
notable
selectivity,
gentle
reaction
conditions,
compatibility
various
groups
as
demonstrated
through
66
examples
display
regioselectivity.
Language: Английский
Dicarbofunctionalization of Vinylarenes with Pyridine and Aldehydes via Photocatalytic Hydrogen Atom Transfer
The Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
89(21), P. 15877 - 15883
Published: Oct. 14, 2024
We
describe
a
metal-free
and
mild
three-component
reaction
utilizing
vinylarenes,
alkyl
aldehydes,
4-cyanopyridine.
In
this
reaction,
the
scope
of
vinylarenes
aldehydes
includes
over
40
examples,
generating
variety
β-pyridinyl
ketones.
Moreover,
potential
applications
method
have
been
demonstrated
by
functionalization
pharmaceutical
molecules.
An
acyl
radical
is
proposed
to
be
produced
via
polarity-matched
hydrogen
atom
transfer
between
triplet-state
diradical
from
benzophenone.
Language: Английский