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.
Organic Letters,
Год журнала:
2024,
Номер
26(22), С. 4727 - 4732
Опубликована: Май 29, 2024
A
visible-light-induced
photocatalyst-free
acylative
pyridylation
of
styrenes
with
4-acyl-1,4-dihydropyridines
(DHPs)
and
4-cyanopyridines
has
been
described,
featuring
mild
reaction
conditions,
a
broad
substrate
scope,
good
functional
group
tolerance.
The
could
also
be
performed
under
sunlight
irradiation
albeit
slightly
lower
conversion.
4-Acyl-1,4-DHPs
serve
dual
role,
acting
as
both
photoreductant
to
reduce
the
cyanopyridine
its
radical
anion
intermediate
precursor
produce
acyl
radical.
mechanism
was
especially
elucidated
through
Hammett
analysis,
quadratic
linear
regression
analysis
by
using
parameters,
σmb
σjj·.
findings
from
further
demonstrate
that
rate-limiting
step
process
is
single
electron
transfer
between
4-acyl-1,4-DHPs
4-cyanopyridines.
Organic Letters,
Год журнала:
2022,
Номер
24(45), С. 8265 - 8270
Опубликована: Ноя. 7, 2022
The
greener
synthesis
of
N-substituted
isonicotinamides
is
high
importance
and
remains
a
significant
challenge
to
the
chemistry
community.
Herein
we
delineated
visible-light-driven,
transition-metal-free,
external-oxidant-free
radical-radical
cross-coupling
reaction
access
via
consecutive
photoinduced
electron
transfer
(ConPET).
utility
this
protocol
highlighted
through
N-terminal
modification
peptides
late-stage
drugs.
Chinese Journal of Chemistry,
Год журнала:
2022,
Номер
40(22), С. 2655 - 2662
Опубликована: Авг. 16, 2022
Comprehensive
Summary
A
general
transition‐metal‐free
visible‐light‐promoted
3‐acetalation
reaction
of
quinoxaline‐2(1
H
)‐ones
was
developed
under
mild
conditions.
By
employing
1,2,3,5‐tetrakis(carbazol‐9‐yl)‐4,6‐dicyanobenzene
(4CzIPN)
as
an
inexpensive
photocatalyst,
and
glyoxylic
acid
acetal
a
radical
source,
various
acetalated
were
constructed
in
moderate
to
good
yields.
Moreover,
the
versatility
this
protocol
is
highlighted
by
successful
application
late‐stage
modification
drug
molecules
functionality
transformations.
The
excellent
antitumor
activity
product
demonstrated
that
streamlined
sustainable
approach
could
have
emerged
powerful
strategy
for
structural
medicinal
chemistry.
Chemistry - A European Journal,
Год журнала:
2024,
Номер
30(31)
Опубликована: Апрель 3, 2024
Abstract
Saturated
heterocycles
are
important
class
of
structural
scaffolds
in
small‐molecule
drugs,
natural
products,
and
synthetic
intermediates.
Here,
we
disclosed
a
metal
free,
mild,
scalable
functionalization
saturated
using
vinylarenes
as
linchpin
approach.
Key
to
success
this
transformation
is
the
employing
simple
cheap
benzophenone
hydrogen
atom
transfer
(HAT)
catalyst.
This
operationally
robust
process
was
used
for
making
diverse
functionalized
heterocycles.
Furthermore,
aldehydes,
alkane,
alcohol
have
been
under
optimized
conditions.
The
potential
pharmaceutical
utility
procedure
has
also
demonstrated
by
late‐stage
bioactive
compounds
molecules.
Initial
mechanism
studies
control
experiments
were
performed
elucidate
reactions
Chinese Journal of Organic Chemistry,
Год журнала:
2022,
Номер
42(12), С. 4292 - 4292
Опубликована: Янв. 1, 2022
Pyrazoles
are
the
most
important
five-membered
N-heterocycles
as
they
present
in
many
natural
products
and
synthetic
drugs.Among
various
pyrazole
derivatives,
4-bromopyrazoles
have
attracted
great
attention
because
not
only
display
significant
biological
activities
physicochemical
properties
but
also
serve
valuable
synthons
organic
chemistry.In
this
manuscript,
an
efficient
eco-friendly
method
for
synthesis
of
through
threecomponent
reaction
hydrazine,
acetylacetone
2-bromomalonate
was
reported
proposal
mechanism
revealed.According
to
mechanism,
hydrazine
reacts
with
afford
firstly,
which
then
converts
4-bromopyrazole
bromination.This
could
be
well
applicable
bromination
other
heterocyclic
compounds.Given
high
oxidation
state
diethyl
2-bromomalonate,
peroxidation
can
avoided
electrolysis
process,
thus
excess
amount
brominating
agent
required.
ACS Omega,
Год журнала:
2023,
Номер
8(6), С. 5877 - 5884
Опубликована: Фев. 6, 2023
Green,
eco-benign,
and
sustainable
synthesis
is
paramount
in
present
chemistry.
Here,
a
facile,
efficient,
[H2-DABCO][HSO4]2
ionic-liquid-catalyzed
one-pot
multicomponent
of
hexahydroquinolines
was
reported
under
ambient
reaction
conditions.
The
1,3-dicarbonyls,
malononitrile,
ammonium
acetate
with
various
aldehydes
the
presence
an
ionic
liquid
catalyst
EtOH
solvent
at
room
temperature
afforded
excellent
yields
(76-100%)
short
time
(5-15
min).
Mild
conditions,
broad
substrate
scope
(28
derivatives),
column-chromatography-free
catalytic
efficiency
good
recyclability
rendered
this
protocol
superior
practical.
greenness
method
assessed
through
eco-score
E-factor.
significant
results
gram-scale
synthetic
conditions
validate
its
applicability
industries
as
well
academia
near
future.
European Journal of Organic Chemistry,
Год журнала:
2024,
Номер
27(28)
Опубликована: Май 20, 2024
Abstract
In
recent
years,
the
functionalization
of
1,3‐butadiene
has
become
an
attractive
strategy
for
constructing
allyl
compounds
with
molecular
and
structural
complexity,
current
research
focuses
on
synthetic
chemistry
organic
synthesis.
Compared
traditional
synthesis
method,
methods
promoted
by
photochemistry
or
electrochemistry
represent
environmentally
friendly
mild
strategy.
this
review,
reactions
under
photochemical/electrochemical
processes
in
years
are
reviewed
according
to
classification
systems,
particular
emphasis
corresponding
reaction
mechanism,
which
lays
a
foundation
further
exploration
new
catalytic
methods.
