A
new
type
of
indole-tethered
terminal
alkynes
was
designed
and
applied
in
a
radical
reaction
with
sulfinates
to
furnish
tetrahydro-γ-carbolines
under
electrochemical
conditions.
Control
experiments
cyclic
voltammetry
disclose
that
the
process
proceeds
via
sequence
anodic
oxidation
indole
moiety
alkyne,
intramolecular
cycloaddition
alkynyl
moiety,
coupling
sulfonyl
radical.
The
features
mild
conditions,
wide
range
substrates,
excellent
stereoselectivity,
which
represent
first
functionalization
alkyne-tethered
indoles
for
synthesis
tetrahydro-γ-carboline
derivatives.
Asian Journal of Organic Chemistry,
Год журнала:
2023,
Номер
12(5)
Опубликована: Апрель 8, 2023
Abstract
Ring‐fused
polycyclic
structures
widely
exist
in
a
myriad
of
natural
products
and
pharmaceutical
molecules.
Consequently,
the
construction
such
from
readily
available
substrates
becomes
an
important
researching
topic
organic
synthesis.
Triggered
by
addition
radicals
to
(activated
or
unactivated)
double
bonds
alkenes,
subsequent
intramolecular
addition/cyclization
leads
compounds.
Following
this
procedure,
variety
functionalized
ring‐fused
were
formed.
Great
achievements
have
been
witnessed
recently.
Those
works
provided
efficient,
atom
economy,
operational
simple
approaches
toward
versatile
alkene‐based
substrates.
Here,
we
summarized
recent
on
formation
via
radical‐triggered
cascade
reactions
alkenes.
Construction
with
no
less
than
3
fused
rings
developed
during
last
decade
included
Review,
corresponding
mechanisms
also
discussed.
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.
The Journal of Organic Chemistry,
Год журнала:
2023,
Номер
88(11), С. 6962 - 6972
Опубликована: Май 22, 2023
An
electrochemical
sulfonylation-triggered
cyclization
reaction
of
indole-tethered
terminal
alkynes
with
sulfinates
as
sulfonyl
sources
has
been
developed,
which
affords
exocyclic
alkenyl
tetrahydrocarbazoles
in
good
chemical
yields.
This
features
convenient
operation
and
tolerates
a
wide
scope
substrates
variety
electronically
sterically
diverse
substituents.
Furthermore,
high
E-stereoselectivity
is
observed
for
this
reaction,
provides
an
efficient
method
the
preparation
functionalized
tetrahydrocarbazole
derivatives.
The Journal of Organic Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Апрель 14, 2025
Tetrahydro-γ-carbolines
are
especially
outstanding
fused
heterocyclic
ring
systems
possessing
significant
biological
activities
in
the
central
nervous
system.
Here,
using
commercially
available
NBE
derivatives
(NBEs),
we
report
an
efficient
protocol
for
one-pot
modular
synthesis
of
4-substituted
tetrahydro-γ-carbolines
via
Catellani/aza-Michael
addition
cascade
from
easily
3-iodo-1-tosyl-1H-indole,
aziridines
and
olefins.
This
approach
exhibits
a
wide
substrate
scope,
good
yields,
scalability,
potential
extension
toward
Mebhydroline
analogues.
The Journal of Organic Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Март 6, 2025
The
synthesis
of
valuable
2a,3-dihydrobenzo[cd]indolines
was
successfully
achieved
by
combining
IPr-Pdcycle-OxaNaphthyl-catalyzed
cross-coupling
and
proton-induced
hydroarylation
in
a
one-pot
method.
In
situ-generated
alkynyl-functionalized
3,3-disubstituted
indolines
were
proved
as
the
key
intermediate,
bearing
broad
scope
substrates
with
diverse
functional
groups
electronic
properties.
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(18), С. 13457 - 13471
Опубликована: Сен. 3, 2024
Organic
molecules
containing
a
difluoroalkyl
group
are
valuable
and
versatile
chemicals
because
of
their
unique
physicochemical
biological
properties.
Accordingly,
the
development
efficient
practical
difluoroalkylation
for
preparation
these
compounds
is
important
attractive.
Herein,
we
demonstrate
photoredox-catalyzed
base-dependent
selective
carbodifluoroalkylation
halodifluoroalkylation
alkenes
using
readily
available
2-(allyloxy)arylaldehydes
[or
2-(allylamino)arylaldehydes]
XCF
Organic Chemistry Frontiers,
Год журнала:
2024,
Номер
11(18), С. 5306 - 5324
Опубликована: Янв. 1, 2024
This
review
summarizes
recent
achievements
in
electrosynthesis
of
organohalides
through
difunctionalization
alkenes
and
alkynes
provides
insights
into
future
directions
for
the
development
field.
Organic & Biomolecular Chemistry,
Год журнала:
2024,
Номер
unknown
Опубликована: Дек. 5, 2024
A
novel
electrochemical
cyclization
reaction
of
N
-acryloyl-indole-3-carboxamides
has
been
developed,
which
provides
a
new
and
efficient
strategy
for
the
synthesis
γ-carbolinone
derivatives.
