Organic Chemistry Frontiers,
Journal Year:
2020,
Volume and Issue:
7(12), P. 1527 - 1569
Published: Jan. 1, 2020
Heterocyclic
alkenes
and
their
derivatives
are
an
important
class
of
reactive
feedstock
valuable
synthons.
This
review
highlights
the
transition-metal-catalyzed
coupling
heterocyclic
alkenesviaa
C–H
functionalization
strategy.
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:
2022,
Volume and Issue:
24(13), P. 2531 - 2535
Published: March 30, 2022
Reported
herein
is
the
efficient
and
atroposelective
construction
of
two
categories
C-N
atropisomers
via
rhodium(III)-catalyzed
C-H
activation
sulfoxonium
ylides
en
route
to
[4+2]
annulation
with
sterically
hindered,
electron-rich
alkynes.
This
reaction
proceeds
high
regio-
enantioselectivity
under
redox-neutral
conditions
a
double-substrate
strategy,
providing
novel
entry
axially
chiral
4-functionalized
1-naphthols.
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.
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.
Organic Letters,
Journal Year:
2020,
Volume and Issue:
22(12), P. 4806 - 4811
Published: June 1, 2020
Site-selective
direct
functionalization
of
an
indole
benzenoid
core
has
been
a
great
challenge
due
to
its
inherently
poor
reactivity.
We
herein
demonstrate
iridium-catalyzed
C4-selective
acylmethylation
indoles
using
α-carbonyl
sulfoxonium
ylides
as
carbene
precursors.
This
method
exhibits
high
efficiency
and
broad
functional
group
compatibility.
The
directing
was
easily
removed
or
converted
other
functionalities
after
the
catalysis.
potential
synthetic
utility
coupling
products
highlighted
by
constructing
medium-sized
polycyclic
indoles.
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.
Organic Letters,
Journal Year:
2020,
Volume and Issue:
22(8), P. 2878 - 2882
Published: March 31, 2020
Rh(III)-catalyzed
C-H
activation
and
cyclization
of
sulfoxonium
ylide
with
acrylates
leads
to
an
efficient
synthesis
indanone
derivatives.
The
reaction
proceeds
under
mild
external
metal-oxidant-free
conditions.
acts
as
a
traceless
directing
group
well
internal
oxidant.
(4
+
1)
Annulation
after
the
formation
carbocyclic
ring,
byproduct
obtained
is
DMSO,
which
can
be
easily
separated.
Organic Letters,
Journal Year:
2021,
Volume and Issue:
23(3), P. 1038 - 1043
Published: Jan. 21, 2021
A
ruthenium-catalyzed
highly
chemoselective
N-alkylation
of
2-pyridones
has
been
developed,
affording
N-alkylated
2-pyridone
derivatives
in
good
yields
and
excellent
N-selectivity.
The
key
to
achieve
this
unprecedented
N–H
rather
than
O–H
insertion
reaction
is
the
use
CpRu(PPh3)2Cl
as
catalyst
sulfoxonium
ylides
alkylation
reagents.
Moreover,
protocol
also
amenable
7-azaindoles
by
slightly
varying
conditions.
Furthermore,
sulfonium
are
suitable
reagents,
providing
selectivity.
