Visible-Light-Mediated Three-Component Alkene 1,2-Alkylpyridylation Reaction Using Alkylboronic Acids as Radical Precursors for the Synthesis of 4-Alkylpyridines
The Journal of Organic Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Март 3, 2025
We
report
the
photocatalyzed
three-component
alkene
1,2-alkylpyridylation
reaction
between
alkylboronic
acids,
4-cyanopyridine,
and
an
olefin
to
achieve
pyridination
alkylation
of
synthesis
structurally
diversified
4-alkylpyridines.
The
readily
available
easily
manipulated
acids
were
used
as
alkyl
radical
precursors.
reactions
take
place
under
mild
conditions
with
a
broad
substrate
scope
are
easy
scale
up
gram
level,
they
therefore
potential
practical
value
for
structural
modification
biologically
active
alkylpyridine
derivatives.
Язык: Английский
Visible‐Light‐Induced Three‐Component Alkylpyridylation of Alkenes Enabled by Electron Donor‐Acceptor Complex
Advanced Synthesis & Catalysis,
Год журнала:
2024,
Номер
366(14), С. 3138 - 3143
Опубликована: Май 11, 2024
Abstract
Visible‐light‐induced
difunctionalization
of
alkenes
is
a
powerful
strategy
for
constructing
complex
molecules.
Herein,
we
disclose
three‐component
1,2‐alkylpyridylation
under
mild
and
photosensitizers‐free
conditions.
UV‐vis
absorption
spectroscopy
studies
NMR
titration
experiments
indicate
that
the
formation
an
EDA
between
4‐alkyl‐DHPs
4‐cyanopyridines.
Primary,
secondary,
tertiary
C(
sp
3
)‐centered
radicals
were
formed
by
homolytic
cleavage
4‐alkyl‐DHPs.
Gram‐scale
synthesis
late‐stage
functionalization
medicinally
relevant
molecules
showed
synthetic
potential
our
methodology.
Язык: Английский
Photoredox-Catalyzed Amino-Radical-Transfer-Mediated Three-Component Alkylarylation of Alkenes
Organic Letters,
Год журнала:
2024,
Номер
26(30), С. 6477 - 6481
Опубликована: Июль 23, 2024
We
herein
reported
a
novel
photoredox-catalyzed
three-component
alkylarylation
of
vinyl
arenes
with
alkylboronic
pinacol
esters
(APEs)
and
cyanoarenes
via
radical
addition/cross-coupling
to
construct
1,1-diarylalkanes.
In
this
transformation,
alkyl
radicals
were
easily
available
by
visible-light-induced
oxidative
N-H
cleavage
morpholine,
which
used
APEs
as
precursor.
Furthermore,
protocol
exhibited
broad
substrate
scope,
enabling
various
styrenes,
APEs,
cyanoarenes,
well
bioactive
molecule
derivatives.
Язык: Английский
Synthesis of Diarylalkanes by Photoreductive 1,2-Diarylation of Alkenes with Aryl Halides and Cyanoaromatics
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(18), С. 13641 - 13653
Опубликована: Сен. 5, 2024
We
report
a
visible
light-induced
photoreductive
strategy
for
three-component
diarylation
of
alkenes
with
aryl
halides
and
cyanoaromatics.
Upon
photoredox
catalysis
tertiary
alkyl
amines
as
the
electron
transfer
agent,
selectively
undergo
halogen
atom
to
generate
radicals
two
C(sp
Язык: Английский
Visible-Light-Induced alkyl-arylation of olefins via a Halogen-Atom Transfer Process
Organic & Biomolecular Chemistry,
Год журнала:
2024,
Номер
22(31), С. 6370 - 6375
Опубликована: Янв. 1, 2024
Visible-light-induced
three-component
1,2-alkyl-arylation
of
alkenes
and
alkyl
radical
addition/cyclization
acrylamides
have
been
realized
using
a
photocatalytic
halogen-atom
transfer
(XAT)
strategy.
Язык: Английский
Photoredox-Catalyzed Regioselective 1,3-Alkoxypyridylation of gem-Difluorocyclopropanes
Organic Letters,
Год журнала:
2024,
Номер
unknown
Опубликована: Дек. 4, 2024
Difluoromethylene
and
pyridine
cores
are
very
important
structural
units
in
medicinal
chemistry.
Herein,
we
report
the
development
of
photoredox-catalyzed
ring-opening
1,3-alkoxypyridylation
gem-difluorinated
cyclopropanes
using
4-cyanopyrines
alcohols,
employing
cyclopropane
radical
cations
as
key
intermediate.
The
reaction
exhibits
high
regioselectivity
under
mild
conditions
can
also
be
practiced
on
gram-scale
synthesis,
telescoped
reaction,
late-stage
functionalization
biological
molecules.
Язык: Английский
Visible-Light-Induced Radical Carbon Oximation of Styrenes Using N-Nitrosoamine and Organic Halides
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
unknown
Опубликована: Дек. 23, 2024
An
efficient
visible-light-induced
radical
carbon
oximation
of
styrenes
with
1-nitrosopyrrolidine
and
organic
halides
is
developed.
The
reaction
proceeds
smoothly
in
the
absence
a
transition
metal
photocatalyst
under
mild
conditions,
producing
wide
range
functionalized
oximes
moderate
to
good
yields.
Mechanistic
studies
reveal
that
involves
generation
nucleophilic
α-amino
alkyl
radicals
subsequent
halogen
atom
transfer
(XAT)
halides.
Язык: Английский