Advanced Synthesis & Catalysis,
Journal Year:
2021,
Volume and Issue:
363(13), P. 3311 - 3317
Published: May 8, 2021
Abstract
A
method
to
synthesize
pyrazolo[1,2‐a]cinnolines
via
rhodium(III)‐catalyzed
C−H
activation
of
pyrazolidinones
and
subsequent
[4+2]
annulation
sulfoxonium
ylides
was
developed.
5‐Substituted
or
5,10‐disubstituted
could
be
obtained
by
slightly
adjusting
the
reaction
conditions.
Gram‐scale
synthesis
practical
transformations
proved
practicability
this
method.
The
mechanism
proposed
in
article
on
basis
preliminary
mechanistic
results
previous
reports.
This
features
simplified
operation,
metal‐oxidant
free,
readily
available
reactants.
magnified
image
Organic Letters,
Journal Year:
2019,
Volume and Issue:
21(12), P. 4812 - 4815
Published: June 13, 2019
A
novel
ruthenium-catalyzed
[5
+
1]
annulation
of
2-alkenylanilines
with
sulfoxonium
ylides
was
developed
for
the
rapid
assembly
highly
functionalized
quinolines.
This
new
catalytic
process
employs
challenging
but
synthetically
ideal
free
amino
functionality
to
achieve
alkenyl
C–H
activation
as
one-carbon
coupling
partners.
Various
2-acylquinolines
could
be
obtained
good
yields
and
excellent
functional
group
tolerance.
Moreover,
potential
synthetic
application
this
methodology
exemplified
by
several
chemical
transformations.
Chinese Journal of Chemistry,
Journal Year:
2019,
Volume and Issue:
37(7), P. 720 - 743
Published: May 15, 2019
As
an
efficient
and
facile
access
to
linear
or
branched
allylic
compounds,
transition
metal-catalyzed
C(sp3)–H
functionalization
reaction
via
η3-allylmetal
intermediates
has
gained
increasing
interest
in
recent
years.
Pd,
Rh,
Ru,
Ir,
Fe
Co-catalyzed
systems
have
all
been
successfully
achieved,
affording
various
compounds
bearing
a
diverse
set
of
functionalities.
Herein,
we
provide
comprehensive
review
this
burgeoning
field
according
different
metal
catalysts.
Organic Letters,
Journal Year:
2019,
Volume and Issue:
21(17), P. 6653 - 6657
Published: Aug. 19, 2019
A
rhodium-catalyzed
annulation
between
aroyl
sulfoxonium
ylides
and
anthranils
has
been
developed
to
synthesize
10H-indolo[1,2-a]indol-10-one
derivatives.
This
reaction
started
with
an
unpredented
(4
+
1)
toward
N-(2-formylphenyl)
indolones,
proceeding
the
sequential
ortho-amination
of
C–H
bond
in
by
insertion
N–H
carbene.
Finally,
Aldol
condensation
constructed
second
indole
ring.
procedure
features
formation
two
C–N
bonds
one
C═C
pot.
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 & Biomolecular Chemistry,
Journal Year:
2019,
Volume and Issue:
17(38), P. 8647 - 8672
Published: Jan. 1, 2019
This
review
highlights
the
developments
in
palladium-catalyzed
allylic
C-H
functionalization
from
early
2014
to
present
date.
π-Allylpalladium
chemistry
emphasizes
research
originating
less
appealing
stoichiometric
Pd(ii)
based
activation
day
green,
step-
and
atom-economical
sustainable
strategy,
wherein
hydrogen
atom
becomes
"leaving
group".
constitutes
a
direct
method,
which
is
essentially
catalytic
presence
of
terminal
oxidant
regenerate
Pd(ii)-species
Pd(0).
The
availability
chiral
ligands,
under
oxidative
conditions,
has
paved
way
realize
asymmetric
Tsuji-Trost
alkylations.
Chemical Communications,
Journal Year:
2019,
Volume and Issue:
56(3), P. 423 - 426
Published: Dec. 4, 2019
Iridium-catalyzed
boron-hydrogen
bond
insertion
reactions
of
trimethylamine-borane
and
sulfoxonium
ylides
have
been
demonstrated,
furnishing
α-boryl
ketones
in
moderate
to
excellent
yields
most
cases
(51
examples;
up
84%).
This
practical
scalable
reaction
showed
broad
substrate
scope,
high
functional-group
compatibility
could
be
applied
late-stage
modification
structurally
complex
drug
compounds.
Further
synthetic
applications
were
also
demonstrated.
Angewandte Chemie International Edition,
Journal Year:
2019,
Volume and Issue:
58(45), P. 16198 - 16202
Published: Sept. 11, 2019
The
functionalization
of
aryl
and
heteroaryls
using
α-carbonyl
sulfoxonium
ylides
without
the
help
a
directing
group
has
remained
so
far
neglected
area,
despite
advantageous
safety
profile
ylides.
Described
herein
are
cyclizations
onto
benzenes,
benzofurans
N-p-toluenesulfonyl
indoles
in
presence
base
HFIP,
whereas
pyrroles
N-methyl
undergo
cyclization
an
iridium
catalyst.
Significantly,
these
two
sets
conditions
chemospecific
for
each
groups
substrates.
The Journal of Organic Chemistry,
Journal Year:
2020,
Volume and Issue:
85(5), P. 3192 - 3201
Published: Jan. 16, 2020
We
report
the
synthesis
of
C6-substituted
isoquinolino[1,2-b]quinazolinones
via
rhodium(III)-catalyzed
C–H
annulation
with
sulfoxonium
ylides
and
evaluation
cytotoxic
activity
scaffold.
This
activation
approach
enables
most
straightforward
convergent
isoquinolino[1,2-b]quinazolines
reported
to
date.
operationally
simple
method
is
compatible
a
wide
variety
ylide
arene
coupling
partners,
permitting
access
diverse
isoquinolino[1,2-b]quinazolines.
shows
high
atom
economy,
generating
H2O
dimethyl
sulfoxide
(DMSO)
as
by-products.
scalable
operates
exquisite
N-lactam
cyclization
selectivity,
thus
enabling
expedient
new
heterocyclic
analogues
featuring
promising
properties.
Organic Letters,
Journal Year:
2020,
Volume and Issue:
22(4), P. 1504 - 1509
Published: Feb. 11, 2020
An
unprecedented
copper-catalyzed
reaction
of
sulfoxonium
ylides
and
anthranils
is
reported
that
enables
an
easy
access
to
2,3-diaroylquinolines
through
a
[4+1+1]
annulation.
Copper-catalyzed
homocoupling
provided
α,α,β-tricarbonyl
ylides,
which
provides
strategy
extend
the
carbon
chain
C–C
bond
formation.
The
utility
products
as
well
mechanistic
details
process
are
presented.
Organic Letters,
Journal Year:
2019,
Volume and Issue:
21(22), P. 9217 - 9222
Published: Nov. 5, 2019
Rhodium(III)-catalyzed
annulative
coupling
of
sulfoxonium
ylides
with
allenoates
was
achieved,
forming
highly
functionalized
cyclopropanes
a
quaternary
carbon
center
by
means
the
ylide
functionality
as
traceless
bifunctional
directing
group
and
C4
synthon
via
an
arene
C–H
activation
cyclopropanation
cascade.
The
protocol
features
simultaneous
formation
three
new
C–C
bonds
in
one
pot
excellent
diastereoselectivity.
resultant
products
could
be
further
transformed
to
diverse
synthetically
useful
compounds.
