Synthesis,
Journal Year:
2023,
Volume and Issue:
56(01), P. 47 - 54
Published: Nov. 23, 2023
Abstract
A
phosphonium-assisted
C–H
cyclization
with
iodonium
ylides
has
been
developed
under
redox-neutral
rhodium(III)
catalysis,
offering
a
wide
variety
of
valuable
isocoumarins
in
moderate
to
good
yields.
This
transformation
proceeds
through
activation,
carbene
insertion,
and
nucleophilic
addition
processes.
The
reaction
occurs
low
catalyst
loading
short
time
does
not
require
an
oxidant.
Chemical Reviews,
Journal Year:
2024,
Volume and Issue:
unknown
Published: Sept. 13, 2024
Hypervalent
iodine(III)
compounds
have
found
wide
application
in
modern
organic
chemistry
as
environmentally
friendly
reagents
and
catalysts.
iodine
are
commonly
used
synthetically
important
halogenations,
oxidations,
aminations,
heterocyclizations,
various
oxidative
functionalizations
of
substrates.
Iodonium
salts
arylating
reagents,
while
iodonium
ylides
imides
excellent
carbene
nitrene
precursors.
Various
derivatives
benziodoxoles,
such
azidobenziodoxoles,
trifluoromethylbenziodoxoles,
alkynylbenziodoxoles,
alkenylbenziodoxoles
group
transfer
the
presence
transition
metal
catalysts,
under
metal-free
conditions,
or
using
photocatalysts
photoirradiation
conditions.
Development
hypervalent
catalytic
systems
discovery
highly
enantioselective
reactions
chiral
represent
a
particularly
recent
achievement
field
chemistry.
Chemical
transformations
promoted
by
many
cases
unique
cannot
be
performed
any
other
common,
non-iodine-based
reagent.
This
review
covers
literature
published
mainly
last
7-8
years,
between
2016
2024.
Organic Letters,
Journal Year:
2023,
Volume and Issue:
25(40), P. 7298 - 7303
Published: Oct. 3, 2023
An
unprecedented
protocol
for
a
Rh(III)-catalyzed
[3
+
2]
annulation
from
simple
and
readily
available
enaminones
iodonium
ylides
has
been
developed.
The
novel
strategy
allows
access
to
new
class
of
structurally
diverse
tetrahydro-indolones
with
high
efficiency
broad
substrate
scope.
In
addition,
this
transformation
represents
the
first
example
selective
alkenyl
C–H
bond
functionalization
enaminones.
Finally,
potential
applications
are
demonstrated
through
gram-scale
reaction
late-stage
modification.
Chemical Communications,
Journal Year:
2023,
Volume and Issue:
59(27), P. 4036 - 4039
Published: Jan. 1, 2023
The
synthesis
of
N-naphthyl
pyrazoles
has
been
realized
by
the
direct
three-component
reactions
enaminones,
aryl
hydrazine
hydrochlorides
and
internal
alkynes
via
Rh(III)
catalysis.
synthetic
employing
simple
substrates
lead
to
simultaneous
construction
dual
cyclic
moieties,
including
a
pyrazole
ring
phenyl
ring,
sequential
formation
two
C-N
three
C-C
bonds.
Organic Letters,
Journal Year:
2023,
Volume and Issue:
25(39), P. 7214 - 7219
Published: Sept. 26, 2023
A
novel
Rh(III)-catalyzed
cascade
alkenyl
C-H
activation/[3
+
2]
annulation/pinacol
rearrangement
reaction
of
enaminones
with
iodonium
ylides
has
been
developed.
This
methodology
provides
a
new
and
straightforward
synthetic
strategy
to
afford
highly
functionalized
2-spirocyclo-pyrrol-3-ones
in
satisfactory
yield
from
readily
available
starting
materials
under
mild
conditions.
Moreover,
gram-scale
reactions
further
derivatization
experiments
are
implemented
demonstrate
the
potential
utility
this
developed
approach.
Organic Letters,
Journal Year:
2023,
Volume and Issue:
25(24), P. 4422 - 4428
Published: June 8, 2023
Presented
herein
is
a
condition-controlled
selective
synthesis
of
pyranone-tethered
indazoles
or
carbazole
derivatives
via
the
cascade
reactions
N-nitrosoanilines
with
iodonium
ylides.
Mechanistically,
formation
former
involves
an
unprecedented
process
including
nitroso
group-directed
C(sp2)–H
bond
alkylation
N-nitrosoaniline
ylide
followed
by
intramolecular
C-nucleophilic
addition
to
moiety,
solvent-assisted
cyclohexanedione
ring
opening,
and
transesterification/annulation.
On
contrary,
latter
initial
annulation
denitrosation.
These
developed
protocols
feature
easily
controllable
selectivity,
mild
reaction
conditions,
clean
sustainable
oxidant
(air),
valuable
products
that
are
structurally
diverse.
In
addition,
utility
was
showcased
their
facile
diverse
transformations
into
synthetically
biologically
interesting
compounds.
The Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
88(7), P. 4833 - 4838
Published: March 22, 2023
A
facile
and
practical
method
for
the
synthesis
of
fused
tricyclic
pyrazolo[5,1-a]isoquinolines
has
been
realized
via
reactions
enaminones,
hydrazine
hydrochloride,
internal
alkynes.
By
means
Rh
catalysis,
extraordinary
high-order
bond
functionalization,
including
transformation
aryl
C–H,
ketone
C═O,
alkenyl
C–N
bonds
in
marks
major
feature
cascade
reactions.
The
results
disclose
individual
advantage
enaminones
design
novel
efficient
synthetic
methods.
Advanced Synthesis & Catalysis,
Journal Year:
2023,
Volume and Issue:
365(11), P. 1817 - 1823
Published: Feb. 7, 2023
Abstract
We
described
an
Rhodium(III)‐catalyzed
divergent
C−H
bond
functionalization
of
N
‐aryl
amidines
with
iodonium
ylides.
Carbazolones
and
zwitterionic
salts
were
diversely
constructed
through
intermolecular
annulation
intramolecular
proton
transfer
under
the
different
reaction
conditions.
This
protocol
is
operationally
simple
tolerates
a
variety
functional
groups.
The
efficient
post‐modification
pharmaceutical
molecules
demonstrates
its
practicability.
The Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
88(9), P. 5348 - 5358
Published: April 3, 2023
A
facile
access
to
isocoumarins
has
been
established
via
rhodium(III)-catalyzed
C-H
bond
activation
and
intramolecular
C-C
cascade
annulation
of
enaminones
cyclic
1,3-dicarbonyl
compounds.
The
synthetic
protocol
features
a
wide
range
substrates
with
high
functional
group
tolerance,
mild
reaction
conditions,
the
selective
cleavage
enaminone
bond.
Notably,
compounds
can
in
situ-generate
iodonium
ylide
as
carbene
precursor
prepare
polycyclic
scaffolds
by
reacting
PhI(OAc)2.
application
this
method
useful
precursors
bioactive
skeletons
is
also
exemplified.
