Photoinduced Co-catalyzed dehydrogenative cyclization of 2-alkenylphenyl carbonyl compounds and mechanistic insights
Organic Chemistry Frontiers,
Год журнала:
2025,
Номер
unknown
Опубликована: Янв. 1, 2025
We
present
two
protocols
for
the
efficient
synthesis
of
substituted
1-naphthols.
DFT
calculations
and
verification
experiments
elucidate
mechanism.
Scale-up
product
conversion
confirm
reaction's
practical
potential.
Язык: Английский
Catalyst-Free Selective Synthesis of E-Tetrasubstituted Olefins via Tandem Reaction of 3-Acetyl-4-phenyl-1-oxaspiro[4.5]deca-3,6,9-triene-2,8-dione with Amine, C–C Bond Breakage, and Proton Transfer
The Journal of Organic Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Фев. 25, 2025
The
Z-
or
E-selective
syntheses
of
tetrasubstituted
olefins
present
big
challenges.
Tremendous
efforts
are
ongoing
to
overcome
this
issue,
especially
for
acyclic
structures.
In
work,
an
E-stereoselective
synthetic
method
through
tandem
reaction
1,4-Michael
addition
3-acetyl-4-phenyl-1-oxaspiro[4.5]deca-3,6,9-triene-2,8-dione
with
amine,
C-C
bond
breakage,
and
proton
transfer
by
intermolecular
hydrogen
bonds
was
revealed
excellent
atom
economy
without
catalysts
additives.
A
diverse
set
E-tetrasubstituted
were
obtained
in
43%
93%
yields
functional
group
tolerance
late-stage
modifications
complex
drug
molecules.
mechanism
proposed
based
on
the
deuterium-labeling
experiment
density
theory
(DFT)
calculation.
Язык: Английский
NHPI-Mediated FeTiO3-Photocatalyzed Semiheterogeneous Decarboxylative Acylarylation of Acrylamides with α-Oxocarboxylic Acids under Nitrogen
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(17), С. 12693 - 12700
Опубликована: Авг. 26, 2024
FeTiO3
has
emerged
as
an
interesting
semiconductor
photocatalyst
in
organic
synthesis.
We
herein
describe
a
visible-light-induced
semiheterogeneous
strategy
for
the
synthesis
of
3-(2-oxoethyl)indolin-2-ones
with
moderate
to
good
yields
and
functional
group
compatibility
using
recyclable
NHPI
redox
catalyst.
Язык: Английский
Intramolecular Dehydrogenative Photocyclization of N-Phenyl-1-naphthamides
Organic Letters,
Год журнала:
2024,
Номер
26(25), С. 5364 - 5369
Опубликована: Июнь 14, 2024
Here,
we
explore
a
dehydrogenative
6π
photocyclization
method
for
Язык: Английский
Metal‐free photocyclization/oxidation cascade constructing quinoline‐2‐ones and tetrahydrocarbazolones
Advanced Synthesis & Catalysis,
Год журнала:
2024,
Номер
366(19), С. 4066 - 4072
Опубликована: Июль 19, 2024
Abstract
We
reported
a
one‐pot
photocyclization/
oxidation
cascade
of
N
‐aryl
acrylamides
to
afford
quinoline‐2‐ones.
Thioxanthone
was
used
as
bifunctional
energy
transfer
agent
mediate
both
photocyclization
and
generation
singlet
oxygen,
the
latter
facilitates
dehydrogenation
dihydroquinoline‐2‐one
intermediate.
This
strategy
also
supports
5‐
endo
‐trig
cyclization
synthesize
tetrahydrocarbazolones
from
phenylamino
cyclohexenones.
Язык: Английский
Gold-Mediated Cyclization of N-Acrylamides via Energy Transfer Photocatalysis
Organic Letters,
Год журнала:
2024,
Номер
unknown
Опубликована: Ноя. 26, 2024
We
disclose
a
gold-mediated
photocyclization
method
for
the
efficient
synthesis
of
acrylamide-derived
β-lactams
and
3,4-dihydroquinolin-2-ones,
two
privileged
bioactive
scaffolds.
The
protocol
proceeds
with
ease,
providing
good
yields
product
while
exhibiting
excellent
functional
group
tolerance
at
low
catalyst
loadings
in
sustainable
solvents.
Additionally,
reaction
times
are
significantly
reduced
compared
prior-art
methods.
Notably,
present
gold
system
exhibits
superior
performance
activating
poorly
conjugated
substrates,
which
typically
unreactive
other
photocatalysts,
highlighting
exceptional
position
this
organogold
among
modern
photocatalysts.
Язык: Английский