The Journal of Organic Chemistry,
Год журнала:
2022,
Номер
87(15), С. 9815 - 9828
Опубликована: Июль 15, 2022
In
this
paper,
a
selective
synthesis
of
indolo[1,2-c]quinazolines
and
indolo[3,2-c]quinolines
through
the
cascade
reactions
2-(1H-indol-2-yl)anilines
with
sulfoxonium
ylides
is
presented.
The
formation
products
involves
generation
carbene
species
from
ylide
its
N–H
bond
insertion
reaction
2-(1H-indol-2-yl)aniline
followed
by
deoxygenative
imine
formation,
intramolecular
N–
or
C–
nucleophilic
addition
aromatization.
This
switchable
was
condition-dependent.
presence
K2CO3
in
CH3CN,
mainly
furnished
indolo[1,2-c]quinazolines.
HOAc
dioxane,
it
selectively
afforded
indolo[3,2-c]quinolines.
addition,
direct
C–H/N–H
functionalization
obtained
provides
convenient
access
to
polycyclic
heteroaromatic
compounds.
These
novel
protocols
have
advantages
such
as
readily
accessible
substrates,
easily
tunable
selectivity,
good
compatibility
diverse
functional
groups,
use
air
cost-free
sustainable
oxidant.
Organic & Biomolecular Chemistry,
Год журнала:
2020,
Номер
18(43), С. 8793 - 8809
Опубликована: Янв. 1, 2020
Sulfur
ylides
first
disclosed
in
1930
started
to
gain
more
attention
the
1960s,
thanks
mainly
studies
by
Corey
and
Chaykovsky
on
their
use
for
preparation
of
strained
rings.
More
recently,
chemistry
these
compounds
has
experienced
important
growth,
part
due
similarity
reactivities
with
diazo
compounds.
This
short
review
provides
an
overview
great
assortment
reactions
sulfoxonium
ylides,
outlining
a
comparison
between
congeners:
sulfonium
Insertion
reactions,
cyclisation
ring-opening
are
highlighted,
giving
particular
catalytic
asymmetric
methodologies.
Chemical Science,
Год журнала:
2021,
Номер
13(5), С. 1192 - 1209
Опубликована: Дек. 8, 2021
Sulfoxonium
ylides
are
important
surrogates
for
diazo
compounds,
and
their
use
in
industry
as
safer
alternatives
has
been
evaluated
during
recent
years.
Beyond
the
known
classical
transformations,
these
have
also
used
a
surprising
plethora
of
novel
intrinsic
chemical
reactions,
especially
Bench
stability
handling
an
advantage
this
class
organosulfur
molecules.
Despite
this,
efficient
asymmetric
specifically
catalytic
enantioselective
versions,
only
recently
reported,
there
specific
reasons
this.
This
perspective
article
covers
topic
from
first
studies
up
to
latest
advances,
giving
personal
perspectives
showing
main
challenges
area
coming
Organic Chemistry Frontiers,
Год журнала:
2022,
Номер
9(16), С. 4388 - 4393
Опубликована: Янв. 1, 2022
The
synthesis
of
3-trifluoromethylisoquinolinones
by
a
ruthenium(
ii
)-catalyzed
C–H
activation/annulation
reaction
benzoic
acids
and
CF
3
-imidoyl
sulfoxonium
ylides
has
been
achieved.
Asian Journal of Organic Chemistry,
Год журнала:
2022,
Номер
11(4)
Опубликована: Март 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.
Angewandte Chemie International Edition,
Год журнала:
2020,
Номер
59(36), С. 15554 - 15559
Опубликована: Апрель 30, 2020
Abstract
The
first
example
of
enantioselective
S−H
insertion
reactions
sulfoxonium
ylides
is
reported.
Under
the
influence
thiourea
catalysis,
excellent
levels
enantiocontrol
(up
to
95
%
ee
)
and
yields
97
%)
are
achieved
for
31
examples
in
aryl
thiols
α‐carbonyl
ylides.
Organic Letters,
Год журнала:
2020,
Номер
22(12), С. 4806 - 4811
Опубликована: Июнь 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.
Angewandte Chemie International Edition,
Год журнала:
2020,
Номер
59(50), С. 22706 - 22713
Опубликована: Сен. 4, 2020
Abstract
We
report
chiral
Rh
III
cyclopentadienyl‐catalyzed
enantioselective
synthesis
of
lactams
and
isochromenes
through
oxidative
[4+1]
[5+1]
annulation,
respectively,
between
arenes
1,3‐enynes.
The
reaction
proceeds
a
C−H
activation,
alkenyl‐to‐allyl
rearrangement,
nucleophilic
cyclization
cascade.
mechanisms
the
annulations
were
elucidated
by
combination
experimental
computational
methods.
DFT
studies
indicated
that,
following
activation
alkyne
insertion,
alkenyl
intermediate
undergoes
δ
‐hydrogen
elimination
allylic
via
six‐membered
ring
transition
state
to
produce
enallene
hydride
intermediate.
Subsequent
insertion
allyl
rearrangement
affords
several
rhodium(III)
intermediates,
rare
η
4
ene‐allyl
species
with
π‐agostic
interaction
SN
2
′‐type
external
attack
nitrogen
nucleophile,
instead
C−N
reductive
elimination,
as
stereodetermining
step.
Organic Letters,
Год журнала:
2021,
Номер
23(3), С. 1038 - 1043
Опубликована: Янв. 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.
Organic & Biomolecular Chemistry,
Год журнала:
2022,
Номер
20(5), С. 1112 - 1116
Опубликована: Янв. 1, 2022
The
direct
synthesis
of
isocoumarin
skeletons
has
been
realized
through
the
Rh(
iii
)-catalyzed
[3
+
3]
annulation
sulfoxonium
ylides
and
iodonium
under
mild
conditions.
