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
Vanadium-Catalyzed Trifluoromethylation/Cyclization of Alkenes and 1,7-Enynes with Togni-II Reagent to Access Trifluoromethylated Oxindoles, Isoquinoline-1,3-diones, and Indeno[1,2-c]quinolines
The Journal of Organic Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Май 28, 2025
A
vanadium-catalyzed
radical
cascade
trifluoromethylation/(bi)cyclization
of
alkenes
and
1,7-enynes
with
Togni-II
reagent
for
the
synthesis
trifluoromethylated
oxindoles,
isoquinoline-1,3-diones,
indeno[1,2-c]quinolines
has
been
developed.
These
transformations
show
broad
substrate
compatibility
high
regioselectivity.
Mechanistic
studies
reveal
that
a
CF3
is
in
situ
generated
to
trigger
ensuing
5-exo
6-exo
cyclization,
as
well
6-exo/5-endo
bicyclization
processes.
Язык: Английский