Organic Letters,
Journal Year:
2022,
Volume and Issue:
24(25), P. 4620 - 4624
Published: June 22, 2022
By
utilizing
an
underexplored
reaction
mode
of
C,N-cyclic
azomethine
imines,
a
catalyst-free
[1+2+3]
cycloaddition/N–N
bond
cleavage
sequential
for
accessing
spiroindolines
with
syn-stereoselectivity
was
developed.
On
the
basis
experimental
results
and
DFT
calculations,
peroxide
ethereal
solvent
were
identified
to
trigger
hydrogen
abstraction
unstable
cycloaddition
adducts,
followed
by
homolytic
N–N
absorption.
Advanced Synthesis & Catalysis,
Journal Year:
2022,
Volume and Issue:
364(13), P. 2211 - 2220
Published: May 21, 2022
Abstract
Reported
herein
is
a
photocatalytic
platform
for
the
vicinal
aminopyridylation
of
indoles.
The
accurate
difunctionalization
reaction
undergoes
tandem
process
involving
radical‐mediated
1,3‐dipolar
cycloaddtion
which
generated
from
single‐electron
oxidation
N
‐aminopyridinium
ylides,
cleavage
N−N
bond
as
well
an
indoline
ring.
electrophilic
pyridyl
and
nucleophilic
amino
groups
can
be
installed
simultaneously
into
wide
range
indoles
under
mild
metal‐free
conditions.
Moreover,
protocol
shows
high
levels
step
atom
economy.
magnified
image
The Chemical Record,
Journal Year:
2023,
Volume and Issue:
23(7)
Published: Jan. 10, 2023
Abstract
Organic
dyes
have
been
actively
studied
as
useful
photocatalysts
because
they
allow
access
to
versatile
structural
flexibility
and
green
synthetic
applications.
The
identification
of
a
new
class
robust
organic
chromophores
is,
therefore,
in
high
demand
increase
diversity
variability.
Although
coumarins
quinolinones
long
acknowledged
chromophores,
their
ability
participate
photoinduced
transformations
is
somewhat
less
familiar.
Fascinated
by
chromophoric
features
adaptable
platform,
our
group
interested
the
fluorescent
bioactive
molecules
development
methods
using
photocatalysts.
This
account
provides
an
overview
recent
progress
discovery
application
light‐absorbing
coumarin
quinolinone
derivatives
photochemistry
medicinal
chemistry.
Organic Chemistry Frontiers,
Journal Year:
2022,
Volume and Issue:
9(8), P. 2129 - 2134
Published: Jan. 1, 2022
This
work
describes
a
photocatalytic
redox-neutral
arylation
of
cyclopropanols
with
cyanoarenes
via
radical-mediated
C–C
and
C–CN
bond
cleavage
to
afford
various
β-arylated
ketones.
Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(12), P. 2414 - 2419
Published: March 15, 2024
We
present
an
innovative
photoinduced
cyanoalkyl
radical
addition
methodology
using
N-iminopyridinium
reagents
derived
from
cyclic
ketones.
Mechanistic
investigations
reveal
the
association
of
excited
Hantzsch
ester
and
iminopyridinium
with
pyridyl
generation.
The
ensuing
cascade
involving
homolytic
N–N
bond
C–C
cleavage
ultimately
leads
to
formation
species,
leading
diverse
Giese-type
products.
method
showcases
versatility
synthetic
utility
in
late-stage
functionalization.
Organic Letters,
Journal Year:
2022,
Volume and Issue:
24(25), P. 4620 - 4624
Published: June 22, 2022
By
utilizing
an
underexplored
reaction
mode
of
C,N-cyclic
azomethine
imines,
a
catalyst-free
[1+2+3]
cycloaddition/N–N
bond
cleavage
sequential
for
accessing
spiroindolines
with
syn-stereoselectivity
was
developed.
On
the
basis
experimental
results
and
DFT
calculations,
peroxide
ethereal
solvent
were
identified
to
trigger
hydrogen
abstraction
unstable
cycloaddition
adducts,
followed
by
homolytic
N–N
absorption.
