Mini-Reviews in Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
21(6), P. 599 - 608
Published: Aug. 22, 2023
Abstract:
2-Oxindole
unit
is
one
of
the
most
important
scaffolds
found
in
several
alkaloids,
natural
products,
antitumor
agents,
pharmaceutically
compounds,
etc.
Molecules
containing
2-
oxindole
moiety
were
first
isolated
from
cat
claw
plant,
widely
distributed
Amazon
jungle.
It
has
now
been
demonstrated
that
these
molecules
are
present
a
wide
range
chemicals
derived
plant
sources.
The
capacity
2-oxindole
to
be
altered
by
various
chemical
groups
provide
unique
biological
activities
can
attributed
its
function
as
framework
for
creating
and
developing
medications.
Since
development
synthetic
methodology,
research
have
developed
protocols
producing
core
bioactive
derivatives.
These
include
traditional
method
transition/non-transition
metal-catalyzed
pathway
synthesis
C3-non-substituted/C3-mono-substituted/C3-di-substituted
core.
Among
those,
C3-substitution-free
quite
challenging
task,
C3-centre
very
reactive.
Syntheses
cores
less
explored
compared
other
substituted
In
this
review
article,
we
mainly
focused
on
showcasing
transition
methodology
2-oxindoles
with
no
substitution
at
C3-centre.
Organic Letters,
Journal Year:
2022,
Volume and Issue:
24(32), P. 5913 - 5917
Published: Aug. 4, 2022
An
N-heterocyclic
carbene-catalyzed
oxidant-,
metal-
and
light-free
iminyl
radical
generation
pathway
stemming
from
the
reaction
of
vinyl
azide
α-bromo
ester
is
uncovered.
This
newly
developed
methodology
successfully
applied
to
redox-neutral
construction
a
number
diversified
phenanthridine
derivatives
with
nice
functional
group
compatibility.
Insights
mechanism
study
reveal
that
this
NHC-catalyzed
transformation
potentially
proceeds
through
an
alkyl
addition-initiated
HAS
process,
as
active
intermediate.
Advanced Synthesis & Catalysis,
Journal Year:
2024,
Volume and Issue:
366(11), P. 2587 - 2595
Published: April 19, 2024
Abstract
A
photochemical
synthesis
of
biologically
relevant
benzyl
oxindoles
is
presented
via
electron‐donor
acceptor
(EDA)
complex
strategy.
This
exogenous
photocatalyst‐free
method
describes
the
formation
a
new
electron
donor‐acceptor
based
on
potassium
carbonate
and
thianthrenium
salts
for
C(
sp
2
)−C(
3
)
bond
formation.
transition‐metal
free
reaction
allows
rapid
increase
in
molecular
complexity
chemical
space,
tolerating
different
functional
groups
as
well
sophisticated
biomolecules.
The
scalability
sustainability
this
highlighted
by
an
important
waste
recovery
protocol.
Mechanistic
investigations
support
EDA
that
induces
radical
chain,
applicability
showcased
straightforward
derivatization
reactions.
Organic Letters,
Journal Year:
2022,
Volume and Issue:
24(25), P. 4615 - 4619
Published: June 22, 2022
N-Polyheterocycles
are
rapidly
accessed
by
N-heterocyclic
carbene
(NHC)
catalysis
through
regioselective
sequential
radical
addition/cyclization
in
the
absence
of
any
metals
or
oxidants.
The
transformation
occurs
under
mild
conditions
and
enjoys
a
wide
substrate
scope
with
excellent
functional
group
compatibility.
Furthermore,
gram-scale
synthesis
is
also
conducted.
Preliminary
mechanistic
studies
reveal
potential
involvement
an
NHC
cation
intermediate.
ChemistryOpen,
Journal Year:
2024,
Volume and Issue:
unknown
Published: July 11, 2024
Abstract
This
review
introduces
the
synthetic
organic
chemical
value
of
α‐bromocarbonyl
compounds
with
tertiary
carbons.
compound
a
carbon
has
been
used
primarily
only
as
radical
initiator
in
atom
transfer
polymerization
(ATRP)
reactions.
However,
recent
development
photo‐radical
reactions
(around
2010),
research
on
use
alkyl
precursors
became
popular
2012).
As
more
examples
were
reported,
studied
not
radicals
but
also
for
their
applications
organometallic
and
ionic
That
is,
act
nucleophiles
well
electrophiles.
The
carbonyl
group
is
attractive
because
it
allows
skeleton
to
be
converted
after
reaction,
being
applied
total
synthesis.
In
our
survey
until
2022,
can
perform
full
range
necessary
synthesis,
including
multi‐component
reactions,
cross‐coupling,
substitution,
cyclization,
rearrangement,
stereospecific
asymmetric
α‐Bromocarbonyl
have
created
new
trend
alkylation,
which
then
had
limited
reaction
patterns
focuses
how
chemistry.
The Journal of Organic Chemistry,
Journal Year:
2025,
Volume and Issue:
unknown
Published: April 24, 2025
A
photoinduced
and
catalyst-free
radical
cyclization
process
for
the
synthesis
of
3,3-disubstituted
oxindoles
is
reported.
This
method
utilizes
readily
available
α-bromoanilides
as
substrates,
showcasing
a
broad
substrate
scope.
The
reaction
mechanism
facilitated
by
photoactivated
charge
transfer
complex
based
on
halogen
bonding
α-bromoanilide
with
TMG
alcohol.
ChemPhotoChem,
Journal Year:
2023,
Volume and Issue:
7(10)
Published: June 24, 2023
Abstract
In
2000,
Fukuzumi
and
co‐workers
reported
a
seminal
study
on
the
photochemical
oxidation
of
benzylic
alcohols
with
visible‐light‐excited
9,10‐phenanthrenequinone
(PQ)
under
argon
atmosphere
(
J.
Am.
Chem.
Soc
.
2000
,
122
8435).
We
optimized
reaction
conditions
they
were
able
to
oxidize
1‐(4‐methoxyphenyl)ethanol
quantitatively
4'‐methoxyacetophenone
in
only
15
min
10
mol
%
PQ
as
photocatalyst
oxygen.
However,
we
observed
significant
decrease
rate
more
electron‐deficient
starting
materials.
To
improve
photooxidation
performance,
designed
high‐yielding
synthetic
route
for
novel,
derivative,
3,6‐bis(trifluoromethyl)‐9,10‐phenanthrenequinone
(PQ‐CF
3
).
Its
efficiency
fast
secondary
was
demonstrated
not
several
electronically
diverse
but
also
aliphatic
substrates.
The
comprehensive
mechanistic
studies
based
Hammett
plot
construction,
kinetic
isotope
experiments,
DFT
computations
suggest
that
pathway
alcohol
is
dependent
electronic
properties
both
catalyst
substrate.
As
key
discovery,
showed
newly
developed
PQ‐CF
operates
highly
efficient
hydrogen
atom
transfer
(HAT)
catalyst.
The Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
89(17), P. 12753 - 12761
Published: Aug. 27, 2024
We
disclose
a
rapid
and
nontoxic
procedure
to
construct
various
oxindoles.
This
method
harnesses
the
power
of
catalytic
amount
quinone
in
synergy
with
Cs2CO3,
showcasing
remarkable
compatibility
wide
range
functional
groups.
Mechanistic
investigations
reveal
that
it
operates
via
radical
pathway,
likely
initiated
by
single-electron
transfer
from
quinone-Cs2CO3
complexes.
pivotal
electron
event
leads
generation
crucial
alkyl
intermediate,
contributing
overall
success
efficacy
transformation.
