Photocatalytic Radical Cascade Cyclization of N-(o-Cyanobiaryl)acrylamides with Sulfonyl Chlorides
The Journal of Organic Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Апрель 2, 2025
A
photoredox-catalyzed
radical
cascade
cyclization
of
N-(o-cyanobiaryl)acrylamides
with
sulfonyl
chlorides
for
the
construction
sulfonyl-containing
pyrido[4,3,2-gh]phenanthridines
has
been
disclosed.
The
developed
synthetic
tool
tolerates
a
broad
range
to
undergo
sequence,
including
addition,
nitrile
insertion,
and
cyclization.
Язык: Английский
Fe-Catalyzed Radical Trifluoromethylation and Cyclization of Ortho-Vinyl Enaminones with 1-(Trifluoromethyl)-1,3-benzo-[d][1,2]iodaoxol-3(1H)-one to Construct Functionalized Quinolines
The Journal of Organic Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Май 19, 2025
Herein,
we
present
a
protocol
for
the
construction
of
functionalized
quinolines,
i.e.,
3-acyl-4-(2,2,2-trifluoro-ethyl)quinolines
(ATFQLs)
4,
from
ortho-vinyl
enaminones
and
1-(trifluoromethyl)-1,3-benzo-[d][1,2]-iodaoxol-3(1H)-one,
which
was
catalyzed
by
FeCp2
promoted
FeCl3
(Lewis
acid)
additives
in
solvents
(i.e.,
acetonitrile
toluene).
This
strategy
first
utilized
FeCp2-catalyzed
functionalization
alkenes
with
trifluoromethyl
radicals.
The
intermediate
formed
captured
ortho-iodobenzoate
substrate,
yielding
3,
then
underwent
FeCl3-catalyzed
elimination
at
higher
temperature
to
form
an
α,β-unsaturated
intermediate.
subsequent
intramolecular
Michael
reaction
yielded
final
target
compound
4.
In
summary,
series
ATFQLs
4
were
synthesized
through
formation
two
bonds
(C═C
C-C).
Язык: Английский
Cascade Reactions of α-Carbonyl Radicals Enabled by Photocatalytic Hydrogen Atom Transfer for the Synthesis of Benzonaphthyridinone Derivatives
Organic Letters,
Год журнала:
2025,
Номер
unknown
Опубликована: Май 27, 2025
A
metal-free
photocatalytic
addition/cyclization
of
the
α-carbonyl
radical
with
N-(2-cyanophenyl)acrylamides
has
been
developed,
providing
novel
benzonaphthyridinone
scaffolds
in
moderate
to
good
yields.
Arylsulfonium
salt
was
employed
as
a
hydrogen
atom
abstractor,
which
effectively
converts
various
ketones
into
radicals.
This
protocol
advantages
including
simple
and
mild
conditions,
broad
substrate
scope,
remarkable
tolerance
toward
diverse
functional
groups.
Язык: Английский