Advanced Synthesis & Catalysis,
Год журнала:
2024,
Номер
366(20), С. 4244 - 4252
Опубликована: Май 25, 2024
Abstract
A
strategy
to
access
fluorinated
spiroindolenines
has
been
developed,
involving
a
selective
functionalization
of
indoles
with
moieties
and
subsequent
catalytic
dearomatization.
Trifluomethylthio
(SCF
3
),
diethyl
phosphono(difluoromethyl)thio
2
P(O)(OEt)
)
(phenylsulfonyl)difluoromethyl
(CF
SO
Ph)
groups
were
embedded
at
the
C2
position
indole
derivatives
substituted
alkynes,
allenes,
allyl
carbonate
C3
position.
gold‐catalyzed
cycloisomerization
gave
five
spiroindolenines,
an
enantioselective
palladium
catalyzed
cyclization
provided
10
spirocyclic
products
up
77%
ee.
Green Chemistry,
Год журнала:
2023,
Номер
25(9), С. 3543 - 3548
Опубликована: Янв. 1, 2023
An
electrochemical
electrophilic
bromination/spirocyclization
of
N
-benzyl-acrylamides
to
brominated
2-azaspiro[4.5]decanes
with
2-bromoethan-1-ol
as
the
brominating
reagent
has
been
developed.
Chemistry - An Asian Journal,
Год журнала:
2023,
Номер
18(9)
Опубликована: Март 15, 2023
Electrochemical
dearomative
spirocyclization
serves
as
a
green
and
sustainable
approach
to
convert
the
flat,
two-dimension
aromatic
feedstock
into
value-added
three-dimension
spirocyclic
architectures.
This
review
highlights
recent
advances,
emphasizes
mechanistic
discussions,
showcases
synthetic
applications
of
this
emerging
versatile
powerful
transformation.
Journal of the American Chemical Society,
Год журнала:
2024,
Номер
146(4), С. 2325 - 2332
Опубликована: Янв. 17, 2024
The
only
known
method
for
the
dearomative
trifluoromethoxylation
of
indoles
is
preliminary,
with
one
substrate
successfully
undergoing
reaction.
In
this
study,
we
not
developed
a
broadly
applicable
indole
but
also
achieved
divergent
by
fine-tuning
reaction
conditions.
Under
optimized
conditions,
silver
salt
and
an
easily
handled
OCF3
reagent,
various
smoothly
underwent
dearomatization
to
afford
diverse
array
ditrifluoromethoxylated
indolines
in
50–84%
isolated
yields
up
37:1
diastereoselectivity,
fluorinated
trifluoromethoxylated
were
obtained
exclusive
trans
selectivity.
addition,
conditions
compatible
other
heteroaromatic
rings
as
well
styrene
moieties.
Chinese Journal of Chemistry,
Год журнала:
2024,
Номер
42(15), С. 1691 - 1698
Опубликована: Март 19, 2024
Comprehensive
Summary
A
novel
electrochemical
multicomponent
cascade
reaction
of
indole‐tethered
alkenes
with
CF
3
SO
2
Na
and
n
‐Bu
4
NI
has
been
developed,
which
enables
the
rapid
assembly
spiropyrrolidinyl‐oxindoles
in
good
yields.
The
experimental
results
DFT
calculations
suggest
that
this
proceeds
through
oxidation
Na,
radical
coupling
alkene,
spirocyclization,
sulfinate,
iodide
substitution,
water
coupling.
This
strategy
features
mild
conditions,
easy‐to‐handle
reactants,
chemical
finding
not
only
enriches
research
contents
but
also
provides
a
green
for
construction
compared
existing
methodologies.
Organic Letters,
Год журнала:
2023,
Номер
25(21), С. 3956 - 3960
Опубликована: Май 18, 2023
A
general
and
robust
strategy
for
the
synthesis
of
phosphonylated
spirocyclic
indolines
has
been
developed
through
Cp2Fe-catalyzed
electrochemical
dearomaztizaion
indoles,
which
proven
challenging
to
achieve
via
chemical
oxidants.
range
3,3-spiroindolines
were
obtained
in
moderate
good
yields
with
excellent
diastereoselectivities.
The
synthetic
application
was
further
illustrated
by
its
easy
scalability
antitumor
activity
product.
Synthesis,
Год журнала:
2023,
Номер
55(18), С. 2873 - 2895
Опубликована: Янв. 24, 2023
Abstract
Spirocyclic
compounds
have
attracted
the
interest
of
synthetic
chemists
because
their
unique
ring
systems
and
utility
in
drug
discovery.
Many
natural
containing
spirocyclic
moieties
skeleton
are
effective
pharmaceuticals.
For
many
redox
processes,
electroorganic
synthesis
is
considered
an
environmentally
friendly
method,
since
use
reagents
with
significant
toxicity
replaced
by
electric
current,
so
amount
waste
often
greatly
reduced.
Therefore,
this
review
summarizes
construction
a
via
electrochemical
strategies
2000.
1
Introduction
2
Electrochemically
Mediated
Synthesis
Spirocyclopropanes
3
Spirooxindoles
4
Spirodienones
5
Other
Heterospirocycles
6
Conclusion
Organic Letters,
Год журнала:
2022,
Номер
24(34), С. 6321 - 6325
Опубликована: Авг. 22, 2022
The
Friedel–Crafts
type
alkylation
of
C2-tethered
thiophenes
has
been
reported
to
be
nonregioselective.
Taking
advantage
the
highly
regioselective
5-exo-trig
spirocyclization
an
electrochemically
generated
amidyl
radical,
we
have
unraveled
electrochemical
dearomative
N-acyl
thiophene-2-sulfonamides.
Various
nucleophilic
agents,
including
carboxylates,
alcohols,
and
fluoride,
are
readily
incorporated
afford
remotely
functionalized
spirocyclic
dihydrothiophenes,
their
novel
scaffolds
shown
exhibit
promising
antitumor
activities.
The Journal of Organic Chemistry,
Год журнала:
2023,
Номер
88(3), С. 1875 - 1883
Опубликована: Янв. 20, 2023
A
new
strategy
of
electrochemical
oxidative
difluoroethylation
to
generate
difluoroethyl
radical
with
sodium
difluoroethylsulfinate
(DFES-Na)
has
been
reported
for
the
first
time.
The
method
allows
quick
access
a
variety
valuable
difluoroethylated
azaheterocycles
including
oxindoles
and
isoquinoline-1,3-diones
via
tandem
difluoroethylation/cyclization
in
moderate
good
yields.
cyclopropyldifluoromethylation
N-arylacrylamides
also
works
well
using
this
strategy.
Moreover,
capture
cyclic
voltammetry
(CV)
experiments
are
carried
out
determine
proposed
mechanism.
Green Chemistry,
Год журнала:
2023,
Номер
25(8), С. 3016 - 3020
Опубликована: Янв. 1, 2023
We
report
the
electrocatalytic
α-hydroxymethylation
of
ketones
using
DMF
as
carbon
source
at
room
temperature
in
air
a
conversion
that
proceeds
without
need
for
toxic
and
expensive
chemical
oxidants
or
metal
catalysts.
