Visible-Light-Induced Decarboxylative Annulation of α,β-Unsaturated Acids with Amines and α-Keto Acids for 2,4-Diarylquinoline Synthesis
Organic Letters,
Год журнала:
2025,
Номер
unknown
Опубликована: Фев. 3, 2025
An
efficient
and
sustainable
approach
for
the
synthesis
of
2,4-diarylquinolines
has
been
developed
via
a
visible-light-promoted
metal-free
three-component
decarboxylative
annulation
pathway.
This
one-pot
protocol
combines
readily
available
feed-stock
α,β-unsaturated
acids,
aromatic
amines,
α-keto
acids
in
cascade
manner
to
access
substituted
quinolines
under
eco-benign
conditions.
Moreover,
mechanistic
insights
suggest
initial
C-C
cross
coupling
followed
by
6π
electrocyclic
afford
desired
products.
The
broad
substrates
scope
excellent
functional
group
tolerance
make
this
more
attractive
synthetically
applicable
toward
construction
complex
N-heterocycles.
Язык: Английский
Organophotoredox-Catalyzed Decarboxylative C–O/N/S Bond Formation: Access to Ampakine APIs and Quinazolinone Alkaloids
Organic Letters,
Год журнала:
2025,
Номер
unknown
Опубликована: Апрель 7, 2025
This
study
describes
a
novel
and
general
protocol
featuring
organophotoredox-catalyzed
intramolecular
decarboxylative
construction
of
carbon-heteroatom
(oxygen,
nitrogen,
sulfur)
bonds,
enabling
direct
access
to
ampakine
APIs
(CX-614
CX-554),
quinazolinone
alkaloids
(deoxyvasicinone
mackinazolinone),
thiazinone
scaffolds
as
well
their
congeners
with
broad
functional
group
tolerance
scalability.
Mechanistic
studies
suggest
radical-polar
crossover
pathway
via
single-electron
oxidation.
Язык: Английский
Iridium/palladium dual photocatalysis for oxidative decarboxylative esterification of alcohols using α-keto acids
Organic Chemistry Frontiers,
Год журнала:
2024,
Номер
unknown
Опубликована: Янв. 1, 2024
Herein,
we
report
an
unprecedented
oxidative
decarboxylative
C–O
cross-coupling
reaction
for
the
esterification
of
feedstock
α-keto
carboxylic
acids
and
alcohols
under
mild
conditions.
Язык: Английский
Photocatalytic Decarboxylative Cross-Coupling of α,β-Unsaturated Acids with Amines for α-Ketoamides via C–N Bond Formation
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(22), С. 16750 - 16758
Опубликована: Ноя. 5, 2024
An
unprecedented
oxidative
decarboxylative
chemical
domain
of
α,β-unsaturated
acids
and
amines
for
C-N
cross-coupled
α-ketoamidation
is
disclosed.
Molecular
oxygen
as
a
source
in
amide
water
the
ketone
segment
furnished
green
sustainable
synthesis
α-ketoamide
from
feedstock
amines.
Mechanistically,
photocatalyst
travels
with
reductive
quenching
cycle,
whereas
pallado-cycle
proceeded
through
bond
formation.
Broad
substrate
scope,
functional
group
tolerance,
CO
Язык: Английский
Electrooxidative Ni‐catalyzed Decarboxylation of Arylacetic Acids towards the Synthesis of carbonyls under Air Conditions
Chemistry - A European Journal,
Год журнала:
2024,
Номер
unknown
Опубликована: Сен. 16, 2024
Abstract
After
systematic
realization
of
decarboxylative
functionalization
carboxylic
acids
under
heating
conditions
in
our
group,
we
herein
reported
an
electrochemical
method
for
Ni‐catalyzed
oxygenation
arylacetic
open
air
conditions.
The
protocol
provided
corresponding
carbonyls
including
aldehydes
and
ketones
moderate
to
satisfactory
yields
with
good
functional
group
tolerance,
furthermore,
the
practicability
advantage
was
highlighted
through
oxidative
decarboxylation
acid‐containing
drugs
preformation
scalable
transformation.
Mechanistic
studies
demonstrated
that
possible
involvement
free
radical
intermediate
conversion.
Язык: Английский