Chinese Journal of Chemistry,
Journal Year:
2024,
Volume and Issue:
42(17), P. 1986 - 1992
Published: April 25, 2024
Comprehensive
Summary
The
rhodium‐catalyzed
C—H
bond
activation
and
cyclization
of
3‐oxopent‐4‐enenitriles
with
alkynes
proceed
efficiently.
Various
2
H
‐pyrans
multiple
substituents
are
achieved
in
good
yields
through
regioselective
formation
C—O
C—C
bonds.
Transformations
involving
hydroxy‐alkynoates
resulted
products
a
furo[3,4‐
b
]pyran
skeleton
via
further
intramolecular
ester
exchange
processes.
Different
from
the
traditional
“1‐oxatrienes
pathway”,
this
method
for
synthesis
useful
possesses
certain
highlights
terms
readily
available
substrates,
stable
easily
derivatized
products,
gentle
convenient
operation
process,
step
atom
economy.
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(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:
2024,
Volume and Issue:
26(1), P. 62 - 67
Published: Jan. 3, 2024
We
have
found
a
chameleonic
reactivity
of
imidoyl
sulfoxonium
ylides.
On
the
one
hand,
ylides
react
with
electron-deficient
reagents,
such
as
alkynyl
esters,
to
lead
formation
1,2-dihydro-pyridines.
The
methyl
group
attached
sulfur
atom
acts
methylene
donor.
other
pyridinium
1,4-zwitterionic
thiolates,
which
leads
functionalized
pyrroles.
Both
transformations
feature
mild
reaction
conditions
and
good
functional
tolerance.
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.
Advanced Synthesis & Catalysis,
Journal Year:
2024,
Volume and Issue:
366(8), P. 1744 - 1750
Published: Feb. 22, 2024
Abstract
The
transmetalation
triggered
rhodium‐catalyzed
C−H
bond
activation
and
tandem
annulation
of
2‐biphenylboronic
acids
with
sulfoxonium
ylides
or
iodonium
has
been
developed.
Various
products
phenanthrenes
were
constructed
under
redox‐neutral
conditions
in
34–86%
yields.
Several
mechanism
exploration
experiments
derivatization
reactions
conducted
sequence
to
gain
a
deeper
understanding
the
process
potential
this
transformation.
It
offers
an
alternative
approach
for
synthesis
phenanthrene
derivatives.
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.
Advanced Synthesis & Catalysis,
Journal Year:
2023,
Volume and Issue:
365(9), P. 1457 - 1464
Published: April 14, 2023
Abstract
In
this
study,
Rh(III)‐catalyzed
C−H
bifunctionalization
and
direct
vinylene
annulation
of
sulfoxonium
ylides
N
‐carbamoylindoles
with
carbonate
was
accomplished,
which
afforded
a
series
naphthalenones
containing
β‐ketosulfoxonium
ylide
moiety,
isocoumarins,
pyrimidones.
This
protocol
featured
mild
conditions,
broad
substrate
scope,
functional‐groups
compatibility.
addition,
related
applications
preliminary
mechanistic
exploratory
were
also
investigated
magnified
image
