Electrochemical Sulfonylation/Cyclization of N-Alkenylacrylamides with Sodium Sulfinates or Sulfonyl Hydrazides
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(15), С. 10660 - 10677
Опубликована: Июль 18, 2024
Two
general
protocols
for
the
regioselective
electrochemically
enabled
sulfonylation
cyclization
of
Язык: Английский
Catalyst-Free Radical Dearomatization of Phenols with Aryldiazonium Tetrafluoroborates and DABCO·(SO2)2
Synlett,
Год журнала:
2025,
Номер
unknown
Опубликована: Март 4, 2025
Abstract
A
catalyst-free,
three-component
dearomatization
of
phenols
with
aryldiazonium
tetrafluoroborates
and
DABCO·(SO2)2
has
been
developed
for
the
synthesis
4-(arylsulfonyl)cyclohex-2,5-dien-1-one
scaffolds.
This
method
offers
mild
reaction
conditions
high
step
efficiency,
providing
a
green
efficient
strategy
phenols.
Mechanistic
studies
indicated
that
this
transformation
relies
on
tandem
radical
sulfur
dioxide
insertion
process.
Язык: Английский
Photoredox Radical Cyclization of o-Vinylaryl Isocyanides and Aryldiazonium Tetrafluoroborates for the Synthesis of 2,4-Disubstituted Quinolines
The Journal of Organic Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Март 23, 2025
Quinolines,
a
significant
part
of
nitrogen-containing
heterocycles,
are
widely
found
in
functional
compounds.
Herin,
photochemical
radical
cyclization
reaction
o-vinylaryl
isocyanides
and
aryldiazonium
tetrafluoroborates,
has
been
reported
to
build
2,4-diaryl
quinolines.
Readily
accessible
aryl
diazonium
salts
were
utilized
as
precursors
at
room
temperature.
This
approach
allowed
good
group
tolerance
substrate
applicability.
Язык: Английский
Alkyl Radical Initiated Cyclization/Cascade for Synthesizing Lactam‐Substituted Alkyl Sulfones
Chinese Journal of Chemistry,
Год журнала:
2024,
Номер
42(16), С. 1853 - 1859
Опубликована: Апрель 17, 2024
Comprehensive
Summary
An
alkyl
radical
initiated
cyclization/tandem
reaction
of
bromides
and
electrophiles
by
using
potassium
metabisulphite
(K
2
S
O
5
)
as
a
connector
is
developed
for
the
synthesis
various
lactam‐substituted
sulfones.
Notably,
this
process
does
not
require
metal
catalyst
or
powder
reductant,
highlighting
its
environmentally
friendly
features.
The
demonstrates
outstanding
substrate
adaptability
high
tolerance
towards
diverse
functional
groups.
Furthermore,
biologically
active
molecules
commercially
available
drugs
with
late‐stage
modification
are
also
highly
compatible
transformation.
Mechanistic
studies
revealed
that
proceeds
through
single‐step
involving
intramolecular
cyclization,
"SO
"
insertion,
external
incorporation.
Язык: Английский
A photoinduced three‐component reaction of thianthrenium salts, DABCO·(SO2)2, and benzyl ether substituted alkenes
Advanced Synthesis & Catalysis,
Год журнала:
2024,
Номер
366(14), С. 3130 - 3137
Опубликована: Май 31, 2024
Abstract
A
photoinduced
three‐component
reaction
of
thianthrenium
salts,
DABCO
⋅
(SO
2
)
,
and
benzyl
ether
substituted
alkenes
is
developed,
affording
δ‐hydroxylsulfones
with
good
functional
group
tolerance.
This
transformation
proceeds
through
an
anti‐Markovnikov
hydrosulfonylation
under
a
mild
condition.
Mechanism
studies
indicates
that
this
undergoes
radical
pathway
involving
sulfur
dioxide
insertion
1,5‐hydrogen
transfer
processes.
Язык: Английский
DABCO‐Mediated Photoelectrochemical Three‐Component Sulfonocyclization of 3‐Aza‐1,5‐dienes
Lu-Cai Ding,
Gui-Hong Yang,
Li Luo
и другие.
Chinese Journal of Chemistry,
Год журнала:
2024,
Номер
unknown
Опубликована: Дек. 2, 2024
Comprehensive
Summary
Herein,
we
report
a
rare
example
of
three‐component
net‐oxidative
sulfonylation
SO
2
surrogate
with
an
oxidatively
activated
radical
precursor
under
mild
and
metal‐
external‐oxidant‐free
conditions.
The
mildness
sustainability
the
reaction
are
enabled
by
photoelectrocatalysis,
3‐aza‐1,5‐dienes,
organotrifluoroborates
1,4‐diazabicyclo[2.2.2]octane
bis(sulfur
dioxide)
adduct
(DABSO)
undergo
sulfonylative
cyclization
to
afford
sulfono
4‐pyrrolin‐2‐ones
in
atom‐economical
manner
broad
substrate
scope
good
functional‐group
tolerance.
protocol
is
amenable
late‐stage
diversification
complex
molecular
architectures
as
well
gram‐scale
synthesis.
Sunlight
could
be
used
light
source,
conducted
all‐solar
mode
using
commercially
available
photovoltaic
panel
generate
electricity
situ
.
Mechanistic
studies
reveal
that
generated
(DABCO),
which
was
generally
innocent
previous
reactions,
functions
electron
shuttle
between
photocatalytic
cycle
reactants.
Язык: Английский
Catalyst-Free Radical Carbosulfonylation of Enamides with Indoles, Aryldiazonium Tetrafluoroborates, and DABCO·(SO2)2
Organic Letters,
Год журнала:
2024,
Номер
unknown
Опубликована: Сен. 23, 2024
Herein,
we
have
developed
a
catalyst-free
four-component
carbosulfonylation
of
enamides
involving
indoles,
DABCO·(SO
Язык: Английский
Electrophotocatalytic Thiocyanation and Sulfonylation Cyclization of Unactivated Alkenes
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
unknown
Опубликована: Дек. 18, 2024
We
report
an
electrophotocatalytic
process
that
enables
the
thiocyanation
and
sulfonylation/cyclization
of
alkenes.
It
is
applicable
to
a
wide
range
unactivated
alkenes,
using
inexpensive
photocatalyst
2,4,6-triphenylpyrylium
tetrafluoroborate
(TPPT)
produce
diverse
array
heterocycles
containing
sulfonyl
thiocyano
groups
with
good
functional
group
tolerance.
The
protocol
operates
under
mild,
chemical
oxidant-
transition-metal-free,
broad
scope
substrates.
Preliminary
mechanistic
studies
suggest
reaction
involves
combination
electrolysis
reductive
quenching
photocatalytic
cycle
TPPT.
Язык: Английский