Organic Chemistry Frontiers,
Год журнала:
2024,
Номер
11(14), С. 3974 - 3981
Опубликована: Янв. 1, 2024
A
defluorinative
cyclization
of
readily
available
trifluoromethyl
enones
with
phosphine
oxides
for
the
synthesis
polysubstituted
furans
is
developed
in
a
pure
water
solution.
A
three-component
reaction
of
trifluoromethyl
enones,
phosphine
oxides,
and
alcohols
in
water
solution
is
developed.
This
defluorinative
occurs
through
a
cascade
process
involving
defluorophosphorylation,
defluoroalkyloxylation,
defluoroheteroannulation,
enabling
the
modular
synthesis
furans
with
four
distinct
substituents:
C2-alkyloxy,
C3-trifluoromethyl,
C4-phosphoryl,
C5-(hetero)aryl
groups.
Moreover,
apart
from
alcohol
substrates,
scope
nucleophiles
could
be
further
extended
to
phenols,
azacycles,
or
sulfonamide.
The Journal of Organic Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Фев. 23, 2025
Trifluoromethyl
enone
emerges
as
a
versatile
and
multifaceted
building
block
in
organic
synthesis.
A
defluorinative
heterocyclization
reaction
of
readily
available
β,β-ditrifluoromethylated
enones
biocompatible
sodium
sulfinates
has
been
developed
for
the
modular
synthesis
densely
functionalized
furans
with
regio-defined
C2,4-bissulfonyl
C3-trifluoromethyl
substitutions.
This
three-component
method
proceeds
through
sequential
sulfonylation
intramolecular
O-cyclization,
enabling
assembly
one
furan
ring,
formation
C-SO2/C–O
bonds,
cleavage
three
C(sp3)-F
bonds
one-pot
manner
under
transition
metal-free
conditions.
Moreover,
obtained
product
can
further
react
benzyne
precursor
to
generate
1,4-epoxynaphthalene
Diels–Alder
cycloaddition.
The
is
also
distinguished
by
its
broad
substrate
scope,
excellent
functional
group
tolerance,
scalability.
Chemical Communications,
Год журнала:
2024,
Номер
60(27), С. 3717 - 3720
Опубликована: Янв. 1, 2024
The
substrate-enabled
switching
of
the
regioselectivity
allows
for
efficient
regiocontrol
via
[4+1]
and
[3+2]
annulations
ninhydrin-derived
MBH
carbonates
with
α,β-unsaturated
ketones
to
access
highly
substituted
furans
cyclopentene.
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(11), С. 7552 - 7560
Опубликована: Май 28, 2024
Herein,
a
palladium-catalyzed
diastereoselective
dearomatization/cross-coupling
cyclization
reaction
between
N-arylacyl
indoles
and
(E)-β-chlorovinyl
ketones
is
reported.
Through
this
cyclization/cycloisomerization
cascade,
series
of
furan-containing
indolines
were
obtained
in
yields
up
to
95%.
The
features
readily
accessible
starting
materials,
benzyl
Pd(II)-catalyzed
cycloisomerization
ketones,
the
sequential
formation
three
bonds
bis-heterocycles,
excellent
diastereoselectivity.
More
importantly,
carbene–secondary
migratory
insertion
proven
be
critical
process
cyclizations.
Organic Letters,
Год журнала:
2024,
Номер
26(25), С. 5329 - 5334
Опубликована: Июнь 13, 2024
Multisubstituted
furans
occupy
a
pivotal
position
within
the
realms
of
synthetic
chemistry
and
pharmacological
science
due
to
their
distinctive
chemical
configurations
inherent
properties.
We
herein
introduce
tandem
difunctionalization
protocol
alcohols
for
efficient
synthesis
multisubstituted
2,3-dihydrofurans
γ-butyrolactones
through
combination
photocatalysis
iron
catalysis
under
mild
conditions.
Photoredox
alcohol
α-C(sp3)–H
activation
Pinner-type
intramolecular
cyclization
are
two
key
processes.
This
method
features
significant
convenience,
economic
benefits,
environmental
friendliness.
Organic & Biomolecular Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Янв. 1, 2025
The
reaction
enabling
the
rapid
construction
of
three
bonds
to
form
furan-bearing
indolo[2,1-
α
]isoquinolines,
which
exhibit
certain
antifungal
activity
in
vitro
,
is
presented.
Molecules,
Год журнала:
2025,
Номер
30(8), С. 1832 - 1832
Опубликована: Апрель 19, 2025
A
novel
method
for
the
efficient
and
straightforward
synthesis
of
tetrasubstituted
furans
is
presented,
employing
a
base-catalyzed
reaction
α-hydroxy
ketones
cyano
compounds.
The
proceeds
under
relatively
mild
conditions,
utilizes
readily
available
starting
materials,
exhibits
good
functional
group
tolerance
high
yields.
Notably,
this
obviates
need
expensive
metal
catalysts
introduces
crucial
groups
such
as
amino
moieties.
Furthermore,
it
avoids
prerequisite
functionalization
substrates,
thereby
enhancing
atomic
economy.
The Journal of Organic Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Апрель 28, 2025
Here,
we
describe
the
synthesis
of
novel
α-carbonyl-α'-vinyl
sulfoxonium
ylides
under
ambient,
catalyst-free,
and
additive-free
conditions,
demonstrating
broad
substrate
scope
scalability
using
β-ketosulfoxonium
α-ynone-esters.
Furthermore,
these
serve
as
versatile
intermediates
for
highly
substituted
furans
via
Brønsted
acid
(p-TsOH)
catalysis
at
130
°C.
This
approach
offers
key
advantages,
including
wide
compatibility,
divergent
product
formation
from
common
precursors,
gram-scale
feasibility,
good
to
excellent
yields.
