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.
Organic Letters,
Journal Year:
2020,
Volume and Issue:
22(14), P. 5706 - 5711
Published: July 8, 2020
Transition-metal-catalyzed
activation
of
inert
C-H
bonds
and
subsequent
C-C
bond
formation
have
emerged
as
powerful
synthetic
tools
for
the
synthesis
elaborate
cyclic
molecules.
In
this
report,
we
introduce
an
efficient
method
3,4-unsubstituted
isocoumarins
adopting
electron-deficient
CpERh
complex
catalyst.
The
use
vinylene
carbonate
a
transfer
reagent
enables
direct
construction
from
readily
available
benzoic
acids,
without
any
external
oxidants
well
bases.
reaction
mechanism
is
evaluated
by
computational
analysis
to
find
unprecedented
"rhodium
shift"
event
within
catalytic
cycle.
Organic & Biomolecular Chemistry,
Journal Year:
2021,
Volume and Issue:
19(7), P. 1438 - 1458
Published: Jan. 1, 2021
The
review
highlighted
diverse
annulations,
including
nitrogen,
oxygen,
sulfur
heterocycles
and
carbocylizations
via
Rh(iii)/Ir(iii)-catalyzed
C–H
functionalization/annulation
with
various
arene
carbene
precursors.
Asian Journal of Organic Chemistry,
Journal Year:
2022,
Volume and Issue:
11(4)
Published: March 23, 2022
Abstract
In
recent
years,
the
transition‐metal‐catalyzed
functionalization
reactions
of
sulfoxonium
ylides
have
been
explored
extensively
because
their
usefulness
as
carbene‐transfer
agents,
since
they
can
produce
metal
carbenes
through
catalysis.
Moreover,
are
safer
and
advantages
simple
handling
good
stability
over
other
counterparts
like
diazo‐compounds.
This
review
article
attempts
to
highlight
advances
in
metal‐catalyzed
C−H
ylides.
Organic Letters,
Journal Year:
2020,
Volume and Issue:
22(4), P. 1375 - 1379
Published: Feb. 3, 2020
The
synthesis
of
indanone
derivatives
by
the
Rh(III)-catalyzed
reaction
α-carbonyl
sulfoxonium
ylides
with
activated
alkenes
is
reported.
shows
a
high
tolerance
for
functional
groups
and
furnishes
variety
substituted
via
formal
[4
+
1]
cycloaddition.
Highly
stable
were
used
as
substrates
in
this
C-H
functionalization,
their
bifunctional
character
could
be
effectively
exploited
using
Rh(III)
catalysis
sequential
double
C-C
bond
formation.
Based
on
mechanistic
studies
including
deuterium-labeling
experiments,
proposed
to
proceed
follows:
oxidative
alkenylation
β-hydride
elimination,
readdition
H-Rh
species,
1,2-carbon
shift
elimination
DMSO,
protonation.
The Journal of Organic Chemistry,
Journal Year:
2021,
Volume and Issue:
87(2), P. 1124 - 1132
Published: Dec. 29, 2021
An
efficient
and
practical
strategy
was
developed
to
synthesize
1,3,4-triaryl-6-trifluoromethylpyridones
from
CF3-imidoyl
sulfoxonium
ylides
cyclopropenones
in
good
excellent
yields.
This
stepwise
[3
+
3]
annulation
reaction
carried
out
under
transition-metal-,
additive-,
solvent-free
conditions,
generating
1
equiv
of
dimethyl
sulfoxide
as
byproduct
tolerating
a
series
functional
groups.
Organic Chemistry Frontiers,
Journal Year:
2024,
Volume and Issue:
11(11), P. 3234 - 3241
Published: Jan. 1, 2024
Herein,
we
present
a
cascade
O–H
double
insertion
reaction
between
I
(III)
/S
(VI)
-ylides,
carboxylic
acids,
and
alcohols
under
metal-free
conditions,
enabling
the
modular
synthesis
of
unsymmetrical
α,α-
O
,
-substituted
ketones.
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.
Advanced Synthesis & Catalysis,
Journal Year:
2021,
Volume and Issue:
363(5), P. 1436 - 1442
Published: Jan. 21, 2021
Abstract
A
highly
efficient
cascade
Rh(III)‐catalyzed
C−H
activation/intramolecular
chemodivergent
cyclization
reaction
of
N‐carbamoylindoles
and
sulfoxonium
ylides
has
been
successfully
achieved
for
the
first
time.
This
synergistic
process
provides
rapid
access
to
functionalized
dihydropyrimidoindolone
tricyclic
[1,3]oxazino[3,4‐
a
]indol‐1‐ones
skeletons
under
redox
neutral
conditions
with
broad
substrate
scope
remarkable
functional‐group
compatibility.
Further
late‐stage
modification
structurally
complex
drug
molecules
mechanistic
studies
were
also
accomplished.
magnified
image
Organic Letters,
Journal Year:
2021,
Volume and Issue:
23(19), P. 7407 - 7411
Published: Sept. 20, 2021
A
lithium-bromide-promoted
nucleophilic
substitution/annulation
cascade
reaction
between
CF3-imidoyl
sulfoxonium
ylides
and
1,3-dicarbonyl
compounds
has
been
established,
the
corresponding
1,2,3-trisubstituted
5-trifluoromethylpyrroles
have
obtained
in
27–78%
yield.
This
features
a
broad
substrate
scope
generates
dimethyl
sulfoxide
H2O
as
byproducts.
