Organic Letters,
Год журнала:
2024,
Номер
26(51), С. 11105 - 11110
Опубликована: Дек. 16, 2024
1,3-Dienes
are
versatile
raw
materials
for
building
molecular
complexity.
We
report
herein
mild
conditions
the
regio-
and
stereoselective
[only
(E)
isomer
obtained]
1,4-carboalkoxylation
of
1,3-dienes.
This
electrochemical
multicomponent
reaction
provides
an
eco-efficient
straightforward
access
to
a
diverse
range
(E)-polyfunctionalized
allyl
ether
products,
without
requiring
any
metal
catalyst.
Abstract
Cyanofunctionalization
of
alkenes
via
radical‐initiated
cyano
migration
was
a
straightforward
pathway
to
access
alkyl
nitriles.
Herein,
By
the
synergistic
merger
photoredox
catalysis
and
Brønsted
base
catalysis,
mild
protocol
alkylcyanation
unactivated
with
protic
C(sp
3
)−H
feedstocks
intramolecular
1,4‐cyano
group
reported.
This
method
enabled
in
an
atom‐,
step‐economy
manner,
delivering
series
γ‐cyanoester
derivatives
moderate
excellent
yields.
Chinese Journal of Chemistry,
Год журнала:
2024,
Номер
unknown
Опубликована: Дек. 2, 2024
Comprehensive
Summary
Herein,
we
report
a
rare
example
of
three‐component
net‐oxidative
sulfonylation
SO
2
surrogate
with
an
oxidatively
activated
radical
precursor
under
mild
and
metal‐
external‐oxidant‐free
conditions.
The
mildness
sustainability
the
reaction
are
enabled
by
photoelectrocatalysis,
3‐aza‐1,5‐dienes,
organotrifluoroborates
1,4‐diazabicyclo[2.2.2]octane
bis(sulfur
dioxide)
adduct
(DABSO)
undergo
sulfonylative
cyclization
to
afford
sulfono
4‐pyrrolin‐2‐ones
in
atom‐economical
manner
broad
substrate
scope
good
functional‐group
tolerance.
protocol
is
amenable
late‐stage
diversification
complex
molecular
architectures
as
well
gram‐scale
synthesis.
Sunlight
could
be
used
light
source,
conducted
all‐solar
mode
using
commercially
available
photovoltaic
panel
generate
electricity
situ
.
Mechanistic
studies
reveal
that
generated
(DABCO),
which
was
generally
innocent
previous
reactions,
functions
electron
shuttle
between
photocatalytic
cycle
reactants.
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
unknown
Опубликована: Дек. 18, 2024
We
report
an
electrophotocatalytic
process
that
enables
the
thiocyanation
and
sulfonylation/cyclization
of
alkenes.
It
is
applicable
to
a
wide
range
unactivated
alkenes,
using
inexpensive
photocatalyst
2,4,6-triphenylpyrylium
tetrafluoroborate
(TPPT)
produce
diverse
array
heterocycles
containing
sulfonyl
thiocyano
groups
with
good
functional
group
tolerance.
The
protocol
operates
under
mild,
chemical
oxidant-
transition-metal-free,
broad
scope
substrates.
Preliminary
mechanistic
studies
suggest
reaction
involves
combination
electrolysis
reductive
quenching
photocatalytic
cycle
TPPT.
Abstract
The
synthesis
of
acylmethylatated
pyrrolo‐quinazolinones
was
developed
via
photo‐induced
cascade
radical
addition/cyclization
N
‐(but‐3‐enyl)quinazolin‐4(3
H
)‐ones
with
sulfoxonium
ylides
using
4CzIPN
as
the
photocatalyst.
This
approach
also
suitable
for
construction
piperidino‐quinazolinones.
protocol
features
mild
conditions,
convenient
operation,
broad
substrate
scope
and
good
functional
group
compatibility.
Organic Letters,
Год журнала:
2024,
Номер
26(51), С. 11105 - 11110
Опубликована: Дек. 16, 2024
1,3-Dienes
are
versatile
raw
materials
for
building
molecular
complexity.
We
report
herein
mild
conditions
the
regio-
and
stereoselective
[only
(E)
isomer
obtained]
1,4-carboalkoxylation
of
1,3-dienes.
This
electrochemical
multicomponent
reaction
provides
an
eco-efficient
straightforward
access
to
a
diverse
range
(E)-polyfunctionalized
allyl
ether
products,
without
requiring
any
metal
catalyst.
