Organic Letters,
Journal Year:
2023,
Volume and Issue:
25(51), P. 9158 - 9163
Published: Dec. 15, 2023
Herein,
a
novel
electrochemical
arene
radical
cation
promoted
dearomative
spirocyclization
of
biaryl
ynones
with
alcohols
is
described,
providing
conceptually
transformation
mode
for
producing
diverse
alkoxylated
spiro[5,5]trienones.
The
catalyst-
and
chemical-oxidant-free
protocol
features
broad
substrate
scope
high
functional
group
tolerance.
Mechanistic
studies
reveal
that
the
generation
via
anodic
single-electron
oxidation
crucial,
sequential
6-endo-dig
cyclization,
dissociation
hemiketal,
oxidation,
nucleophilic
attack
alcohols.
New Journal of Chemistry,
Journal Year:
2022,
Volume and Issue:
46(42), P. 20061 - 20064
Published: Jan. 1, 2022
An
efficient
6-
exo-trig
radical
cascade
reaction
of
biaryl
ynones
with
NaNO
2
was
developed
to
afford
nitro-functionalized
spiro[5.5]trienones
yields
up
88%.
Molecules,
Journal Year:
2024,
Volume and Issue:
29(2), P. 458 - 458
Published: Jan. 17, 2024
The
oxidative
radical
cascade
cyclization
of
alkynes
has
emerged
as
a
versatile
strategy
for
the
efficient
construction
diverse
structural
units
and
complex
molecules
in
organic
chemistry.
This
work
reports
an
alkyl
initiated
5-exo-trig
biaryl
ynones
with
1,4-dihydropyridines
to
selectively
synthesize
indenones.
Organic Letters,
Journal Year:
2023,
Volume and Issue:
25(51), P. 9158 - 9163
Published: Dec. 15, 2023
Herein,
a
novel
electrochemical
arene
radical
cation
promoted
dearomative
spirocyclization
of
biaryl
ynones
with
alcohols
is
described,
providing
conceptually
transformation
mode
for
producing
diverse
alkoxylated
spiro[5,5]trienones.
The
catalyst-
and
chemical-oxidant-free
protocol
features
broad
substrate
scope
high
functional
group
tolerance.
Mechanistic
studies
reveal
that
the
generation
via
anodic
single-electron
oxidation
crucial,
sequential
6-endo-dig
cyclization,
dissociation
hemiketal,
oxidation,
nucleophilic
attack
alcohols.
