The Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
88(16), P. 12121 - 12130
Published: July 29, 2023
We
describe
a
visible-light
photoredox-catalyzed
alkylation/arylative
cyclization
of
N-acrylamides─from
2-arylindoles,
2-arylbenzimidazoles,
or
N-substituted
anilines─with
ketone-derived
dihydroquinazolinones,
accessing
indolo-
and
benzimidazolo[2,1-a]isoquinolines
2-oxindoles.
The
consecutive
incorporation
alkyl-
aryl-carbogenic
motifs
across
C=C
bond
via
formal
cleavage
ketone
α-C-C
arene
C-H
bonds
leads
to
the
formation
five-
six-membered
rings,
with
an
all-carbon
quaternary
stereocenter.
This
dicarbofunctionalization
elaborates
aromatization-driven
radical
C-C
functionalization
unactivated
aliphatic
ketones
construct
diverse
cyclic
structures
functionality
tolerance.
Organic Letters,
Journal Year:
2023,
Volume and Issue:
25(38), P. 7014 - 7019
Published: Sept. 18, 2023
Organoelectrophotocatalytic
generation
of
acyl
radicals
from
formamides
and
aldehydes
to
synthesize
acylated
3-CF3-2-oxindoles
has
been
developed.
This
protocol
features
a
monocatalytic
system
using
9,10-phenanthrenequinone
(PQ)
both
as
catalyst
hydrogen
atom
transfer
(HAT)
reagent,
which
avoids
the
use
an
external
HAT
metal
oxidant.
A
variety
have
obtained
in
satisfactory
yields
CF3-substituted
N-arylacrylamides
via
tandem
radical
cyclization.
Green Chemistry,
Journal Year:
2024,
Volume and Issue:
26(12), P. 7331 - 7336
Published: Jan. 1, 2024
A
novel
photocatalytic
acylation
strategy
was
developed
harnessing
tetrabutylammonium
decatungstate
(TBADT)
as
a
hydrogen
atom
transfer
(HAT)
photocatalyst
to
facilitate
the
direct
coupling
of
aldehydes
with
N-heterocycles
at
ambient
temperature.
Organic Letters,
Journal Year:
2021,
Volume and Issue:
23(20), P. 7787 - 7791
Published: Sept. 28, 2021
A
mild
and
efficient
visible-light-induced
radical
difluoromethylation/cyclization
of
unactivated
alkenes
toward
the
synthesis
substituted
quinazolinones
with
easily
accessible
difluoromethyltriphenylphosphonium
bromide
has
been
developed.
The
transformation
advantages
wide
functional
group
compatibility,
a
broad
substrate
scope,
operational
simplicity.
benign
protocol
offers
facile
access
to
pharmaceutically
valuable
difluoromethylated
polycyclic
quinazolinones.
Green Chemistry,
Journal Year:
2022,
Volume and Issue:
24(4), P. 1732 - 1737
Published: Jan. 1, 2022
A
general
visible-light-induced
catalyst-/additive-free
strategy
was
developed
for
the
construction
of
various
aroylated
heterocyclesunder
air
and
room
temperature
conditions.
ACS Catalysis,
Journal Year:
2022,
Volume and Issue:
12(21), P. 13549 - 13554
Published: Oct. 20, 2022
A
dual
photocatalytic
protocol
was
developed
to
generate
acyl
radicals
from
readily
available
aldehydes
via
hydrogen
atom
transfer
(HAT).
Synergistic
cooperation,
being
supported
by
DFT
studies,
between
earth-abundant
iron(III)chloride
and
9,10-diphenylanthracene
(DPA)
activate
the
aldehyde
for
a
HAT
step
proved
be
an
efficient,
economic,
green
route
hydroacylation
of
electron-deficient
alkenes
under
UV-light
irradiation
with
broad
functional
group
compatibility.
This
methodology
can
conveniently
scaled
up
applied
produce
valuable
materials
renewable
feedstock
chemicals.
ACS Sustainable Chemistry & Engineering,
Journal Year:
2023,
Volume and Issue:
11(3), P. 910 - 920
Published: Jan. 11, 2023
The
first
piezochemically
driven
decarboxylative
coupling
of
the
C–H
bond
was
developed.
agitation
BaTiO3
via
ball
milling
converts
mechanical
energy
into
electrical
potential,
leading
to
production
a
benzoyl
radical
single-electron
transfer
pathway
analogous
photocatalytic
reaction.
This
mechanoredox
catalytic
strategy
synthesize
C3-acylated
quinoxalin-2(1H)-ones
requires
no
solvent,
short
reaction
time,
and
simple
handling
skills,
exhibiting
promising
potential
in
large-scale
chemical
manufacturing.
Asian Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
12(5)
Published: April 8, 2023
Abstract
Ring‐fused
polycyclic
structures
widely
exist
in
a
myriad
of
natural
products
and
pharmaceutical
molecules.
Consequently,
the
construction
such
from
readily
available
substrates
becomes
an
important
researching
topic
organic
synthesis.
Triggered
by
addition
radicals
to
(activated
or
unactivated)
double
bonds
alkenes,
subsequent
intramolecular
addition/cyclization
leads
compounds.
Following
this
procedure,
variety
functionalized
ring‐fused
were
formed.
Great
achievements
have
been
witnessed
recently.
Those
works
provided
efficient,
atom
economy,
operational
simple
approaches
toward
versatile
alkene‐based
substrates.
Here,
we
summarized
recent
on
formation
via
radical‐triggered
cascade
reactions
alkenes.
Construction
with
no
less
than
3
fused
rings
developed
during
last
decade
included
Review,
corresponding
mechanisms
also
discussed.
