The Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
88(15), P. 10662 - 10669
Published: July 14, 2023
A
novel
and
efficient
Rh(III)-catalyzed
direct
C-H
bond
tandem
annulation
of
N-nitrosoanilines
with
1,3-dicarbonyl
compounds
through
two
cleavage
was
developed.
This
protocol
provides
a
rapid
access
to
series
valuable
tetrahydrocarbazol-4-ones
the
feature
readily
available
starting
materials,
broad
functional
group
tolerance,
in
situ
generation
carbene
precursors.
Importantly,
some
reaction
products
exhibited
promising
antiproliferative
activity
cancer
cell
lines.
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.
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(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.
Organic Letters,
Journal Year:
2022,
Volume and Issue:
24(29), P. 5281 - 5286
Published: July 18, 2022
A
Ru(II)-catalyzed
decarbonylative
alkylation
and
annulation
of
salicylaldehydes
2-aminobenzaldehydes
with
iodonium
ylides
has
been
developed
for
the
synthesis
dibenzo[b,d]furans
NH-free
carbazolones.
The
reaction
proceeds
smoothly
under
mild
conditions
a
low
catalyst
loading
broad
substrate
compatibility.
Notably,
hydroxy
free
amino
groups
were
demonstrated
to
be
effective
directing
groups,
enabling
successful
aldehyde
C–H
bond
activation
subsequent
decarbonylation
inexpensive
Ru(II)
catalyst.
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.
Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(24), P. 5136 - 5140
Published: June 7, 2024
Herein,
we
report
a
rhodium-catalyzed
C–H
activation/[4+2]
cyclization
reaction
between
α,β-unsaturated
amides
and
iodonium
ylides
for
the
synthesis
of
novel
7,8-dihydroquinoline-2,5-diones
analogues.
This
protocol
provides
series
pyridones
fused
with
saturated
cycles
good
functional
group
compatibility,
water
air
tolerance,
to
excellent
yields
under
mild
green
conditions.
Additionally,
scale-up
can
be
smoothly
performed
as
low
0.25
mol
%
catalyst
loading.
Recycling
experiments
different
transformation
were
also
carried
out
demonstrate
potential
synthetic
utility
this
protocol.
Organic & Biomolecular Chemistry,
Journal Year:
2022,
Volume and Issue:
21(1), P. 24 - 38
Published: Nov. 23, 2022
The
metal-catalyzed
successive
activation
and
functionalization
of
arene/heteroarene
is
one
the
most
fundamental
transformations
in
organic
synthesis
leads
to
privileged
scaffolds
natural
products,
pharmaceuticals,
agrochemicals,
fine
chemicals.
Particularly,
transition-metal-catalyzed
C-H
arenes
with
carbene
precursors
via
metal
migratory
insertion
has
been
well
studied.
As
a
result,
diverse
have
evaluated,
such
as
diazo
compounds,
sulfoxonium
ylides,
triazoles,
etc.
In
addition,
there
significant
developments
use
iodonium
ylides
recent
years,
these
reactions
proceed
high
efficiencies
selectivities.
This
review
provides
comprehensive
overview
functionalizations,
including
scope,
limitations,
their
potential
synthetic
applications.
Chemical Communications,
Journal Year:
2022,
Volume and Issue:
58(97), P. 13483 - 13486
Published: Jan. 1, 2022
A
straightforward
approach
to
synthesise
isocoumarins
via
Rh(III)-catalyzed
C-H/C-C
bond
activation/annulation
cascade
of
enaminones
and
iodonium
ylides
has
been
explored.
The
established
protocol
is
characterized
by
an
exceedingly
simple
reaction
system,
high
regioselectivity
good
functional
group
tolerance.
Moreover,
this
strategy
may
provide
a
new
route
cleavage
the
C(sp2)-C(O)
unstrained
ketones.
Organic Letters,
Journal Year:
2023,
Volume and Issue:
25(22), P. 4022 - 4027
Published: May 26, 2023
A
novel
Rh-catalyzed
cascade
reaction
of
pyridotriazoles
with
iodonium
ylides
is
reported.
This
one-pot
procedure
involves
a
triazole-directed
ortho-position
C–H
carbene
insertion,
followed
by
intramolecular
denitrogenation
annulation.
It
was
noteworthy
that
this
provided
straightforward
access
to
1H-isochromene
frameworks
excellent
yields
(up
94%
yield).