Green Synthesis of 3,4‐Unsubstituted Isoquinolones through Rhodium(III)‐Catalyzed C−H Activation and Annulation in Ethanol
European Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
26(44)
Published: Sept. 27, 2023
Abstract
A
mild
and
convenient
synthesis
of
3,4‐unsubstituted
isoquinolones
has
been
achieved
from
N
‐methoxybenzamides
vinylene
carbonate
as
an
acetylene
surrogate
with
a
versatile
rhodium(III)
catalyst.
The
reaction
proceeded
at
room
temperature
in
biomass
derived
ethanol
solvent.
This
protocol
avoids
the
use
stoichiometric
external
oxidant,
served
internal
oxidant.
C−H/N−H
activation
annulation
manifold
broad
substrate
scope
excellent
levels
regioselectivities.
preliminary
mechanistic
studies
suggest
facile
reversible
chelation‐assisted
C−H
rhodation.
Diversification
provide
access
to
4‐substituted
isoquinolines,
which
are
complementary
previously
reported
protocols.
Language: Английский
Synthesis of 3‐Methyleneisoindolin‐1‐ones via Rhodium(III)‐Catalyzed C−H/N−H Activation and Annulation of N‐Methoxybenzamides with Potassium Vinyltrifluoroborate
Chemistry - An Asian Journal,
Journal Year:
2024,
Volume and Issue:
19(22)
Published: Aug. 9, 2024
Abstract
Isoindolinones
are
vital
heterocyclic
compounds
in
medicinal
chemistry,
notable
for
their
diverse
bioactivities.
Significant
attention
has
been
devoted
to
preparation;
however,
existing
methods
unsuitable
constructing
unsubstituted
3‐methyleneisoindolin‐1‐ones.
Herein,
we
present
a
rhodium(III)‐catalyzed
method
synthesizing
3‐methyleneisoindolin‐1‐ones
via
C−H/N−H
activation
and
annulation
of
N
‐methoxybenzamides
with
potassium
(ethenyl)trifluoroborate.
This
approach
offers
mild
reaction
conditions,
high
regioselectivity,
efficient
yields.
Interestingly,
sterically
demanding
or
‐methoxyaromaticamides
resulted
the
formation
2‐vinyl(hetero)aromatic
amides
instead
Mechanistic
insights
suggest
rhodacycle
intermediate
pathway,
highlighting
method's
potential
developing
new
bioactive
isoindolinone
derivatives.
Language: Английский
Palladium‐Catalyzed Direct Alkynylation of Carbazoles with Alkynyl Bromides
European Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
27(40)
Published: June 18, 2024
Abstract
Carbazole
derivatives
are
vital
in
medicinal
and
materials
chemistry,
yet
accessing
diverse
substitutions
remains
challenging.
Here,
we
introduce
a
regioselective
approach
for
C1
C8
alkynylation
of
carbazoles
via
palladium‐catalyzed
C−H
activation.
This
method
provides
direct
route
to
mono‐
di‐alkynylated
derivatives,
addressing
the
scarcity
alkynylated
carbazole‐based
materials.
Our
study
broadens
synthetic
toolbox
carbazole
functionalization,
offering
potential
applications
optoelectronics,
bio‐imaging,
beyond,
while
contributing
developing
sustainable
activation
methodologies.
Language: Английский