Radical
difunctionalization
of
aliphatic
alkynes
provides
direct
access
to
valuable
multi-substituted
alkenes,
but
achieving
a
high
level
chemo-
and
stereo-control
remains
formidable
challenge.
Herein
we
report
novel
photoredox
neutral
alkyne
through
functional
group
migration
followed
by
radical-polar
crossover
energy
transfer-enabled
stereoconvergent
isomerization
alkenes.
In
this
sequence,
hydroxyalkyl
an
aryl
are
incorporated
concomitantly
into
alkyne,
leading
diversely
functionalized
E-allyl
alcohols.
The
scope
is
noteworthy,
the
reaction
tolerates
containing
hydrogen
donating
C-H
bonds
which
prone
intramolecular
atom
transfer.
protocol
features
broad
compatibility,
product
diversity
exclusive
stereoselectivity,
thus
providing
practical
strategy
for
elusive
radical
unactivated
alkynes.
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(9), С. 6117 - 6125
Опубликована: Апрель 24, 2024
The
first
paired
electrolysis-enabled
arylation
of
quinoxalin-2(1H)-ones
was
achieved
using
cyanoarenes
as
the
reagents.
A
variety
3-arylquinoxalin-2(1H)-ones
with
various
important
functional
groups
were
obtained
in
moderate
to
good
yields
under
metal-
and
chemical
oxidant-free
conditions.
With
a
pair
reductive
oxidative
processes
occurring
among
substrates
reaction
intermediates,
power
consumption
can
be
dramatically
reduced.
Organic Letters,
Год журнала:
2023,
Номер
25(16), С. 2793 - 2797
Опубликована: Апрель 18, 2023
A
unique,
facile,
and
straightforward
electrochemical
oxidative
annulation
of
inactivated
propargyl
aryl
ethers
with
sulfonyl
hydrazides
leading
to
3-sulfonated
2H-chromenes
has
been
achieved.
Significantly,
this
protocol
involves
a
green
approach
that
works
under
mild
reaction
conditions
using
constant
current
in
an
undivided
cell
is
devoid
oxidants
catalysts.
Notably,
the
process
exhibited
broad
scope
functional
group
tolerance
deliver
would
represent
alternative
sustainable
strategy
versus
conventional
chromene
synthesis.
Organic Letters,
Год журнала:
2024,
Номер
26(29), С. 6114 - 6119
Опубликована: Июль 5, 2024
Difunctionalization
of
alkynes
has
gained
a
lot
interest
in
current
organic
chemistry.
Herein,
we
developed
an
electrophotocatalytic
multicomponent
cascade
reaction
and
indoles
with
sulfinic
acid
sodium
salts
using
elemental
tellurium
as
the
source.
Using
synergistic
anodic
oxidation
visible-light
irradiation,
various
β-(telluro)vinyl
sulfones
have
been
prepared.
This
strategy
features
mild
conditions,
excellent
substrate
scope,
readily
available
starting
materials,
great
functional
group
tolerance.
Journal of Chemical Education,
Год журнала:
2025,
Номер
unknown
Опубликована: Фев. 27, 2025
Multicomponent
reactions
(MCRs)
are
fascinating
chemical
processes
where
three
or
more
starting
materials
come
together
to
form
a
single
product.
By
exploring
various
MCRs,
second-year
undergraduate
students
learn
about
the
synergy
between
different
functional
groups
and
how
they
influence
reactivity,
power
of
streamlined
approach
compared
conventional
stepwise
reactions,
critical
thinking
MCR
mechanisms.
Herein,
we
introduce
valuable
synthetic
method
for
constructing
heterocyclic
compounds
through
multiple-component
condensation/cycloaddition
process.
Specifically,
focus
on
1,4-dihydropyridine
(1,4-DHP),
privileged
N-heterocyclic
scaffold
widely
used
in
medicinal
chemistry,
particularly
4-aryl-3,5-dicarboxylated
derivatives.
The
experiment
provides
an
excellent
opportunity
explore
concept
green
chemistry
while
synthesizing
structurally
interesting
useful
molecules
using
readily
available
materials.
achieve
this
condensation
reaction
2-furaldehyde
(furfural),
acetoacetic
acid
tert-butyl
ester,
ammonium
acetate.
Key
features
teaching
include
following.
(1)
reaction:
involves
concise,
multicomponent
with
short
time.
(2)
Catalyst-free:
Notably,
proceeds
without
need
solvents
catalysts.
(3)
Visually
striking
system:
change
system
is
visually
evident,
enhancing
learning
experience.
(4)
Useful
methodology
drug
synthesis:
has
practical
implications
synthesis.
We
successfully
implemented
proposal
across
five
parallel
student
groups,
involving
approximately
150
participants.
experimental
procedures
encompass
organic
synthesis,
thin-layer
chromatography
(TLC),
nuclear
magnetic
resonance
(NMR)
analysis.
Organic Letters,
Год журнала:
2024,
Номер
26(16), С. 3441 - 3446
Опубликована: Апрель 16, 2024
Herein,
a
cooperative
N-heterocyclic
carbene-
and
palladium-catalyzed
three-component
reaction
of
alkynes
with
aldehydes
fluoroalkyl
iodides
is
developed.
A
series
biologically
valuable
CF2R-incorporated
α-substituted
enones
was
obtained
in
moderate
to
good
yields.
This
mild
catalytic
method
exhibits
exclusive
regio-
stereoselectivity,
excellent
functional
group
tolerance,
broad
substrate
scope
including
terminal
internal
alkynes.
Mechanistic
investigations
disclose
that
this
alkyne
fluoroalkylacylation
proceeds
via
radical
relay
process
which
vinyl
serve
as
putative
intermediates.
Chemical Communications,
Год журнала:
2023,
Номер
59(20), С. 2915 - 2918
Опубликована: Янв. 1, 2023
Herein,
we
present
an
efficient
electrochemical
method
for
synthesizing
2-alkyl-4-phenylalkan-2-ols
through
electrochemically
driven
cathodic
reductive
coupling
of
the
terminal
and
internal
acetylenes
with
unactivated
aliphatic
ketones
under
mild
conditions.
The
process
proceeds
a
ketyl
radical,
which
then
activates
aryl
acetylene
causes
complete
reduction
triple
bond
moiety.
This
strategy
is
environmentally
benign
exhibits
broad
substrate
scope
ubiquitously
available
starting
materials.
Molecules,
Год журнала:
2023,
Номер
28(6), С. 2667 - 2667
Опубликована: Март 15, 2023
The
synthetic
strategies
of
oxime
derivatives
participating
in
radical-type
reactions
have
been
rapidly
developed
the
last
few
decades.
Among
them,
N–O
bond
cleavage
esters
leading
to
formation
nitrogen-centered
radicals
triggers
adjacent
C–C
produce
carbon-centered
free
radicals,
which
has
virtually
used
organic
synthesis
recent
years.
Herein,
we
summarized
radical
involving
and
through
this
special
reaction
form,
including
those
from
acyl
ester
cyclic
ketoxime
derivatives.
These
contents
were
systematically
classified
according
different
types.
In
review,
after
2021
included,
with
emphasis
on
substrate
scope
mechanism.
