Photoinduced Pd-Catalyzed Dearomative 2,5-Difunctionalizition of Furans via Cascade C–C/C–O Bond Formation
Organic Letters,
Год журнала:
2024,
Номер
26(5), С. 1083 - 1087
Опубликована: Янв. 26, 2024
We
report
an
efficient
and
mild
approach
for
radical
dearomatization
via
photoinduced
palladium-catalyzed
reaction
of
three
components
(i.e.,
furans,
alcohols,
bromoalkanes).
In
this
strategy,
various
functionalized
spiro-heterocycles
were
prepared
from
furans
in
one
step
cascade
C–C/C–O
bond
formation
under
redox
neutral
conditions.
Язык: Английский
Access to Functionalized Indenes via Palladium‐Catalyzed Homolytic Cleavage of a Furan C−O Bond
Advanced Synthesis & Catalysis,
Год журнала:
2024,
Номер
366(17), С. 3597 - 3602
Опубликована: Июнь 19, 2024
Abstract
A
photoinduced
palladium‐catalyzed
ring‐opening
hydroarylation
of
furans
to
form
functionalized
indenes
was
achieved
via
an
intramolecular
reductive
coupling
aryl
bromide
with
furan
using
silane
as
the
reductant.
Deuterium
tracking
and
DFT
analysis
revealed
a
reasonable
reaction
pathway
involving:
1)
homolytic
cleavage
C−O
bond
induced
by
α
‐allyl
radical;
2)
1,6‐H
atom
transfer
from
carbon
oxygen.
Язык: Английский
Hexafluoroisopropanol (HFIP)-Promoted Hydrodifluoroalkylation of Furans and Vinyl Ethers Using Difluorinated Silyl Enol Ethers for the Synthesis of gem-Difluorinated Ethers
The Journal of Organic Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Фев. 18, 2025
A
hexafluoroisopropanol
(HFIP)-promoted
hydrodifluoroalkylation
of
furans
and
vinyl
ethers
with
difluorinated
silyl
enol
has
been
developed.
Because
the
inherent
electron
richer
nature
poor
nucleophilicity
ethers,
employment
simple
as
substrates
for
nucleophilic
dearomatization
without
a
metal
or
stoichiometric
chemical
oxidizing
reagent
is
challenging,
especially
considering
rearomatization
driving
force
ring
fragmentation
furan
system.
This
protocol
exploits
formation
oxocarbenium
intermediate
from
using
HFIP
proton
source
to
allow
addition
which
provides
an
efficient
synthetic
strategy
install
gem-difluorinated
group
into
heterocycles.
Язык: Английский
Dearomatization of Aromatic Compounds: A Decade Review
Asian Journal of Organic Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Май 28, 2025
Abstract
Dearomatization
offers
an
efficient
strategy
for
directly
converting
arenes
into
cyclic
molecules.
In
this
review,
we
discuss
representative
examples
of
dearomatization
reactions
through
five
modes:
(1)
radical
dearomatization,
(2)
halofunctionalization‐dearomatization,
in
which
three‐membered
intermediates
were
frequently
involved,
(3)
nucleophilic
mainly
about
electron‐rich
arenes,
(4)
oxidative
and
(5)
reductive
dearomatization.
Compared
to
heteroarenes,
simple
benzene
are
more
challenging
participate
reactions.
recent
years,
fewer
reports
have
focused
on
benzene.
Heteroarenes,
inherently
or
easily
activated,
tend
undergo
readily.
This
review
highlights
a
decade
progress
including
indoles,
benzofurans,
benzothiophenes,
thiophenes,
furans,
naphthols,
naphthalenes,
quinolines,
pyridines,
nitrobenzenes,
benzenes.
It
also
analyzes
their
mechanisms
strategies.
We
hope
will
aid
future
research
field.
Язык: Английский
Electrochemical Dearomative Spirocyclization of N‐Acyl Sulfonamides in a Continuous‐Flow Cell†
Chinese Journal of Chemistry,
Год журнала:
2023,
Номер
42(9), С. 980 - 984
Опубликована: Дек. 26, 2023
Comprehensive
Summary
The
development
of
efficient
and
sustainable
methods
to
obtain
spirocyclic
compounds
is
significance
as
these
structures
are
widely
found
in
pharmaceuticals
agrochemicals.
Herein,
we
disclose
an
electrochemical
dearomative
spirocyclization
N
‐acyl
sulfonamides
a
continuous‐flow
cell.
reaction
simple
without
external
catalysts
or
supporting
electrolytes
could
be
applied
decagram‐scale
synthesis.
Язык: Английский
Towards tetrasubstituted furans through rearrangement and cyclodimerization of acetylenic ketones
Organic & Biomolecular Chemistry,
Год журнала:
2024,
Номер
22(6), С. 1172 - 1175
Опубликована: Янв. 1, 2024
We
developed
a
simple
route
to
phosphorus-containing
tetrasubstituted
furans
via
the
phosphane
borane
complex-enabled
rearrangement
and
cyclodimerization
of
acetylenic
ketones
under
basic
conditions.
Язык: Английский
Synthesis of Functionalized Furans: Three‐Component Reactions Involving Ketene Dithioacetals, Acetylenes, and Phosphines to Generate Phosphorus Ylides or <i>N</i>‐Acyliminophosphoranes
Advanced Synthesis & Catalysis,
Год журнала:
2024,
Номер
366(15), С. 3346 - 3353
Опубликована: Июнь 5, 2024
Abstract
Synthesis
of
new
polysubstituted
furans
incorporating
reactive
phosphorus
ylides
or
N
‐acyliminophosphoranes
was
achieved
by
the
heterocyclization
flexible
α‐acyl
ketene
dithioacetals.
This
one‐pot
tandem
reaction
initiated
acyl‐directed
desulfurative
Sonogashira
coupling,
followed
1,6‐addition
phosphine
to
in
situ‐generated
enynone
and
subsequent
5‐
exo
‐
dig
cyclization,
as
well
phosphoranation.
The
selectivity
toward
two
products,
i.
e.
α‐phosphorus
vs.
α‐
‐acyliminophosphoranes‐substituted
furans,
determined
both
electron‐deficient
acetylenes
copper
salts.
Язык: Английский
Recent Developments in Copper‐Catalyzed Annulations for Synthesis of Spirooxindoles
The Chemical Record,
Год журнала:
2024,
Номер
24(11)
Опубликована: Окт. 22, 2024
Abstract
Spirooxindoles
represent
a
special
scaffold
for
pharmaceuticals
and
natural
products,
significant
advancements
have
been
achieved
in
their
synthesis
recent
years.
Among
these,
transition
metal
catalysis,
particularly
copper
has
emerged
as
an
efficient
reliable
method
the
of
spirooxindoles.
Based
on
different
reaction
types,
two
distinct
substrate
types
summarized
classified
by
us
constructing
spirooxindole
scaffolds
via
intramolecular
intermolecular
annulations.
This
review
outlines
latest
copper‐catalyzed
cyclization
reactions
synthesizing
spirooxindoles
provides
detailed
insights
into
annulation
possible
mechanisms.
Язык: Английский
Halogen Radical-Enabled Dearomatization of N-Arylpropiolamides via Photoinduced Sequential Halogenation/Spirocyclization/Oxidation Process
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
unknown
Опубликована: Дек. 4, 2024
Here
we
report
a
strategy
that
eliminates
the
need
for
photocatalysts
and
external
additives,
which
provides
an
operable
mild
method
halogen
radical-enabled
dearomatization
of
N-arylpropiolamides
under
oxygen
atmosphere
at
room
temperature.
The
is
applicable
to
wide
range
substrates,
extending
beyond
limited
scope
p-methoxyl
N-phenylpropynamides.
Furthermore,
several
functional
synthetic
intermediates
anticancer
bioactive
molecules
were
successfully
derived
from
3-halogenated
azaspiro[4.5]trienones.
Язык: Английский