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.
Organic & Biomolecular Chemistry,
Год журнала:
2022,
Номер
20(37), С. 7467 - 7471
Опубликована: Янв. 1, 2022
An
intramolecular
cyclization
reaction
of
β-fluoroalkyl
β-amino
cyclic
ketones
with
t
-BuONO
and
PPh
3
/CCl
4
has
been
developed,
which
provides
novel
access
to
trifluoromethylated
fused
tricyclic
pyrazole
derivatives.
The Journal of Organic Chemistry,
Год журнала:
2023,
Номер
88(15), С. 10586 - 10598
Опубликована: Июль 14, 2023
Spiro[indoline-3,3'-pyrrolidine]
and
spiro[indoline-3,3'-piperidine]
derivatives
were
synthesized
in
a
substitution-controlled
manner
under
the
catalysis
of
cationic
gold(I)
species
presence
Hantzsch
ester
(HEH).
The
optimal
reaction
condition
was
determined
by
screening,
functional
group
tolerances
these
two
pathways
examined
readily
synthetic
substrates.
endo
exo
selectivities
cyclizations
elucidated
density
theory
calculations,
plausible
mechanism
for
transformations
proposed.
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.
