Convenient
access
to
6-alkylsulfonylmethyl
phenanthridines
has
been
demonstrated
both
under
thermal
and
visible-light
photoredox-catalyzed
conditions.
A
cascade
of
radical
cyclization
is
triggered
on
exposure
biphenyl
vinyl
azides
the
in-situ
generated
alkyl
sulfonyl
radicals
from
4-substituted
Hanztsch
esters
in
presence
an
SO2
surrogate.
Transition
metal-free,
mild
reaction
conditions,
broad
substrate
scope
constitute
some
highlights
approach.
Also,
synthetic
utility
accessed
demonstrated.
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(8), С. 5409 - 5422
Опубликована: Апрель 2, 2024
An
oxidant-assisted
tandem
sulfonylation/cyclization
of
electron-deficient
alkenes
with
4-alkyl-substituted
Hantzsch
esters
and
Na2S2O5
for
the
preparation
3-alkylsulfonylated
oxindoles
under
mild
conditions
in
absence
a
photocatalyst
transition
metal
catalyst
is
established.
The
mechanism
studies
show
that
alkyl
radicals,
which
come
from
cleavage
C–C
bond
4-substituted
oxidant
conditions,
subsequently
undergo
situ
insertion
sulfur
dioxide
to
generate
crucial
alkylsulfonyl
radical
intermediates.
This
three-component
reaction
provides
an
efficient
facile
route
construction
alkylsulfonylated
avoids
use
highly
toxic
chlorides
or
hydrazines
as
sources.
Asian Journal of Organic Chemistry,
Год журнала:
2024,
Номер
13(5)
Опубликована: Март 5, 2024
Abstract
Convenient
access
to
6‐alkylsulfonylmethyl
phenanthridines
has
been
demonstrated
both
under
non‐catalytic
thermal
and
visible‐light
photoredox‐catalyzed
conditions.
A
cascade
of
radical
cyclization
is
triggered
by
the
exposure
biphenyl
vinyl
azides
in‐situ
generated
alkyl
sulfonyl
radicals
from
4‐substituted
Hanztsch
esters
in
presence
an
SO
2
surrogate.
Transition
metal‐free,
mild
reaction
conditions,
broad
substrate
scope
constitute
some
highlights
approach.
Also,
synthetic
utility
accessed
demonstrated.
Chemical Communications,
Год журнала:
2024,
Номер
60(56), С. 7228 - 7231
Опубликована: Янв. 1, 2024
A
visible-light-induced
K
2
S
O
8
-promoted
cascade
sulfonation/cyclization
reaction
to
afford
a
series
of
sulfonated
quinolino[2,1-
b
]quinazolinones
has
been
developed
under
mild
conditions.
Organic & Biomolecular Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Янв. 1, 2025
A
visible-light-induced
deoxygenative
alkylation/cyclization
of
acrylamides
with
alcohols
activated
by
CS
2
has
been
developed
using
xanthate
salts
as
alkyl
radical
precursors
in
the
presence
tricyclohexylphosphine.
The Journal of Organic Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Март 16, 2025
A
photocatalytic
radical
sulfonarylation
of
N-arylacrylamides
via
a
three-component
cascade
cyclopropyl
alcohol
ring
opening/sulfur
dioxide
insertion/sulfonyl
addition/cyclization
sequence
has
been
developed.
This
method
employs
alcohols
as
the
precursors
β-carbonyl
alkyl
radicals
and
Na2S2O5
cheap
source
sulfur
dioxide.
By
using
this
procedure,
wide
variety
γ-keto-sulfone-substituted
oxindoles
were
facilely
synthesized.
The Journal of Organic Chemistry,
Год журнала:
2023,
Номер
88(21), С. 15374 - 15388
Опубликована: Окт. 23, 2023
We
report
an
organo-photocatalyzed
carboacylation
reaction
that
offers
a
springboard
to
create
chemical
complexity
in
diversity-driven
approach.
The
modular
one-pot
method
uses
feedstock
aldehydes
and
alcohols
as
acyl
surrogates
commercially
available
Eosin
Y
the
photoredox
catalyst,
making
it
simple
affordable
introduce
structural
diversity.
Several
biologically
relevant
skeletons
have
been
easily
synthesized
under
mild
conditions
presence
of
visible
light
irradiation
by
fostering
radical
acylation/cyclization
cascade.
proposed
mechanism
was
further
illuminated
number
spectroscopic
studies.
Furthermore,
we
applied
this
protocol
for
late-stage
functionalization
pharmaceuticals
blockbuster
drugs.
