TCT-Mediated and Water-Controlled Synthesis of Benzofuran-3(2H)-ones Bearing a Quaternary Carbon Center via a Radical Process Using Dimethyl Sulfoxide as a Dual Synthon
The Journal of Organic Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Апрель 10, 2025
An
efficient
and
attractive
method
for
the
synthesis
of
valuable
benzofuran-3(2H)-one
derivatives
bearing
a
quaternary
center
in
one
step
by
employing
dimethyl
sulfoxide
(DMSO)
as
dual
synthon
under
metal-free
conditions
has
been
developed.
In
this
reaction,
DMSO
activated
cyanuric
chloride
(TCT)
provides
two
different
units
(CH3
SMe)
target
molecules,
construction
carbon
benzofuran-3(2H)-ones
can
be
controlled
addition
water.
Furthermore,
functional
group
compatibility
synthetic
value
were
demonstrated
scope
evaluation
gram-scale
experiments.
The
mechanistic
studies
show
that
reaction
may
proceed
via
radical
process.
Язык: Английский
Acid-Regulated Selective Synthesis of Benzofuran Derivatives via Single-Component BDA Retro-Aldol/Michael Addition Cascade and [4 + 2] Cycloaddition Reactions
The Journal of Organic Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Май 20, 2025
The
acid-controlled
single-component
retro-aldol/Michael
addition
cascade
reaction
and
[4
+
2]
cycloaddition
of
benzofuran-derived
azadienes
(BDAs)
are
reported
for
the
first
time.
Under
conditions
trifluoromethanesulfonic
acid
as
catalyst
with
water,
BDAs
initiate
retro-aldol
reaction,
followed
by
a
1,4-Michael
addition,
yielding
(arylmethylene)bis(dibenzofuran)
products
excellent
yields
broad
substrate
applicability.
This
represents
application
in
reaction.
In
contrast,
absence
water
boron
trifluoride
etherate
catalyst,
undergo
constructing
spiro[benzofuran-2,3'-benzofuro[3,2-b]pyridine]
framework
high
diastereoselectivity.
method
features
mild
atom
economy,
provides
new
approach
benzofuran
scaffold
derivatives.
Язык: Английский
Synthesis of Tetracyclic-Fused Dihydroindeno[2,1-b]chromenes via Palladium-Catalyzed Alkyne Insertion and C–H Bond Activation
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
unknown
Опубликована: Дек. 25, 2024
An
unprecedented
Pd-catalyzed
cascade
alkyne
insertion/Heck/C–H
activation
reaction
of
o-iodophenyl
alkenyl
ethers
and
diarylacetylenes
has
been
developed.
Diversified
tetracyclic-fused
dihydroindeno[2,1-b]chromenes
bearing
a
quaternary
center
were
constructed
in
an
efficient,
straightforward,
atom-economic
way
with
good
to
excellent
yields.
The
protocol
features
high
bonding
efficiency,
operational
simplicity,
broad
substrate
scope,
easy
scale-up.
Язык: Английский