The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
unknown
Опубликована: Дек. 20, 2024
A
convenient
electrochemical
oxidative
cascade
cyclization
of
alkenes
equipped
with
pendant
alcohols
general
nucleophiles
was
developed.
Using
readily
available
diarylmethanimine
and
carboxylic
acids
as
nucleophilic
sources,
a
broad
range
internal
alkene
terminal
substrates
could
produce
RCO2-
Ar2CN-functionalized
O-heterocycles
in
moderate
to
high
yields
without
the
requirement
for
external
oxidants
metals.
These
resulting
products
can
subsequently
be
hydrolyzed
yield
valuable
NH2-
OH-functionalized
tetrahydrofurans
tetrahydropyranes
under
mild
conditions.
Importantly,
efficient
conversion
secondary
alcohol
amines
complete
inversion
configuration
enhances
methodology,
enabling
construction
2-aryl-3-amino
tetrahydrofuran
complementary
diastereoselectivity.
Green Chemistry,
Год журнала:
2024,
Номер
26(7), С. 4199 - 4208
Опубликована: Янв. 1, 2024
A
new
photoelectrocatalytic
mode
permits
the
synthesis
of
polycyclic
pyrimidin-4-ones
through
dehydrogenative
cyclization
malonates
with
unactivated
alkenes.
We
have
developed
a
mild
and
efficient
electrochemical
reduction
approach
employing
aryl
diazonium
salts
as
dual
synthons
to
synthesize
valuable
multi-substituted
pyrazoles
for
the
first
time.
Organic & Biomolecular Chemistry,
Год журнала:
2023,
Номер
21(16), С. 3317 - 3322
Опубликована: Янв. 1, 2023
A
variety
of
azaheterocycle-fused
piperidines
and
pyrrolidines
bearing
CF3
CHF2
functionalities
were
obtained
using
CF3SO2Na
CHF2SO2Na
by
visible
light
photocatalysis.
This
protocol
involves
a
radical
cascade
cyclization
via
tandem
tri-
difluoromethylation-arylation
pendent
unactivated
alkenes.
Benzimidazole,
imidazole,
theophylline,
purine,
indole
serve
as
applicable
anchors,
thereby
enriching
the
structural
diversity
piperidine
pyrrolidine
derivatives.
method
features
mild,
additive-free
transition
metal-free
conditions.
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(4), С. 2343 - 2350
Опубликована: Янв. 29, 2024
This
work
describes
the
possibility
to
combine
multicomponent
chemistry
and
multienzymes
cascade
transformations
in
a
unique
reactive
framework
yield
highly
functionalized
1,4-benzoxazines
under
favorable
heterogeneous
conditions.
The
synthetic
scheme
involved
generation
situ
of
electrophilic
quinone
intermediates
tyrosol
esters
catalyzed
by
lipase
M
tyrosinase
followed
nucleophilic
1,6-Michael
addition
selected
α-amino
acid
methyl
esters,
successive
intramolecular
lactonization
aromatization
processes.
immobilization
on
electroactive
lignin
nanoparticles
improved
sustainability
recyclability
overall
system.
Advanced Synthesis & Catalysis,
Год журнала:
2024,
Номер
366(5), С. 1152 - 1157
Опубликована: Янв. 9, 2024
Abstract
This
research
presents
a
method
for
the
oxidative
selenylation
and
thiolylation
of
Morita‐Baylis‐Hillman
adducts
through
constant‐current
electrolysis
in
an
undivided
cell
at
room
temperature.
The
reaction
enables
direct
production
trisubstituted
(
Z
)‐allyl
aryl
selenides
sulfides
with
yields
27–98%.
A
wide
variety
different
functionalities
are
well
tolerated
under
these
conditions.
strategy
could
be
carried
out
on
gram
scale
several
synthetic
transformations
were
accomplished
construction
other
allyl
selenide
derivatives.
Control
experiments
mechanistic
studies
indicate
radical
or
ionic
addition
pathway
this
electrochemical
transformation.
Organic Chemistry Frontiers,
Год журнала:
2023,
Номер
10(15), С. 3786 - 3791
Опубликована: Янв. 1, 2023
An
unprecedented
and
sustainable
electrochemically
driven
oxidative
5-
exo-dig
radical
cyclization
of
N
-propargylbenzamides
with
alcohols
for
the
synthesis
structurally
diverse
oxazole
ketals
is
described.
Abstract
Indoline‐fused
polycyclic
scaffolds
are
virtually
universal
in
biological
and
pharmaceutical.
Here
we
demonstrate
a
facile
electrooxidative
cascade
cyclization
for
indoline‐based
derivatives,
employing
amidyl
radicals
with
ynones
under
mild
conditions.
The
efficient
method
enables
the
formation
of
two
new
C−N
C−C
bonds
single
step
high
regioselectivity.
Various
tetracyclic
6/5/6/6
skeletons
can
be
achieved
through
biscyclization/dehydrogenation
process.
Additionally,
this
electrochemical
strategy
proceeds
sustainable
metal‐
oxidant‐free
condition,
H
2
being
solely
byproduct.
