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.
Chemical Society Reviews,
Journal Year:
2018,
Volume and Issue:
47(17), P. 6603 - 6743
Published: Jan. 1, 2018
The
present
review
is
devoted
to
summarizing
the
recent
advances
(2015-2017)
in
field
of
metal-catalysed
group-directed
C-H
functionalisation.
In
order
clearly
showcase
molecular
diversity
that
can
now
be
accessed
by
means
directed
functionalisation,
whole
organized
following
directing
groups
installed
on
a
substrate.
Its
aim
comprehensive
reference
work,
where
specific
group
easily
found,
together
with
transformations
which
have
been
carried
out
it.
Hence,
primary
format
this
schemes
accompanied
concise
explanatory
text,
are
ordered
sections
according
their
chemical
structure.
feature
typical
substrates
used,
products
obtained
as
well
required
reaction
conditions.
Importantly,
each
example
commented
respect
most
important
positive
features
and
drawbacks,
aspects
such
selectivity,
substrate
scope,
conditions,
removal,
greenness.
targeted
readership
both
experts
functionalisation
chemistry
(to
provide
overview
progress
made
last
years)
and,
even
more
so,
all
organic
chemists
who
want
introduce
way
thinking
for
design
straightforward,
efficient
step-economic
synthetic
routes
towards
molecules
interest
them.
Accordingly,
should
particular
also
scientists
from
industrial
R&D
sector.
overall
goal
promote
application
reactions
outside
research
dedicated
method
development
establishing
it
valuable
archetype
contemporary
R&D,
comparable
role
cross-coupling
play
date.
Chemical Reviews,
Journal Year:
2019,
Volume and Issue:
119(14), P. 8701 - 8780
Published: June 25, 2019
Organosulfur
compounds
have
long
played
a
vital
role
in
organic
chemistry
and
the
development
of
novel
chemical
structures
architectures.
Prominent
among
these
organosulfur
are
those
involving
sulfur(IV)
center,
which
been
subject
countless
investigations
over
more
than
hundred
years.
In
addition
to
list
textbook
sulfur-based
reactions,
there
has
sustained
interest
organosulfur(IV)
recent
Of
particular
within
is
ease
with
synthetic
chemist
can
effect
wide
range
transformations
through
either
bond
formation
or
cleavage
at
sulfur.
This
review
aims
cover
developments
past
decade
molecules
provide
insight
into
both
reactions
critically
rely
on
this
versatile
element
diverse
scaffolds
that
thereby
be
synthesized.
Chemical Reviews,
Journal Year:
2022,
Volume and Issue:
122(15), P. 12544 - 12747
Published: July 17, 2022
1,1,1,3,3,3-Hexafluoroisopropanol
(HFIP)
is
a
polar,
strongly
hydrogen
bond-donating
solvent
that
has
found
numerous
uses
in
organic
synthesis
due
to
its
ability
stabilize
ionic
species,
transfer
protons,
and
engage
range
of
other
intermolecular
interactions.
The
use
this
exponentially
increased
the
past
decade
become
choice
some
areas,
such
as
C–H
functionalization
chemistry.
In
review,
following
brief
history
HFIP
an
overview
physical
properties,
literature
examples
reactions
using
or
additive
are
presented,
emphasizing
effect
each
reaction.
Organic Letters,
Journal Year:
2017,
Volume and Issue:
19(19), P. 5256 - 5259
Published: Sept. 13, 2017
Sulfoxonium
ylides
act
as
an
efficient
carbene
precursor
in
rhodium(III)-catalyzed
C-H
acylmethlyation
of
a
variety
arenes
assisted
by
different
chelating
groups,
and
both
aryl-
alkyl-substituted
β-carbonyl
sulfoxonium
are
applicable.
The
system
proceeded
under
redox-neutral
conditions
with
broad
scope,
high
efficiency,
functional
group
tolerance.
Organic Chemistry Frontiers,
Journal Year:
2017,
Volume and Issue:
5(6), P. 998 - 1002
Published: Dec. 22, 2017
Sulfoxonium
ylides
acts
as
a
bifunctional
C2-synthon
in
Rh(iii)-catalyzed
redox-neutral
annulative
coupling
with
arenes
for
the
synthesis
of
N-heterocycles
and
carbocycles.
Organic Letters,
Journal Year:
2018,
Volume and Issue:
20(5), P. 1396 - 1399
Published: Feb. 22, 2018
A
rhodium-catalyzed
annulation
between
ethyl
benzimidates
and
α-
aroyl
sulfur
ylides
was
developed,
affording
a
series
of
pyrano[4,3,2-ij]isoquinoline
derivatives
in
moderate
to
good
yields
with
functional
group
compatibility.
The
procedure
featured
dual
ortho-C–H
functionalization
cyclization
one
pot.
optoelectronic
properties
those
fused
heteroarenes
were
tested
by
UV/vis
fluorescence
spectrometers.
Organic Letters,
Journal Year:
2019,
Volume and Issue:
21(8), P. 2541 - 2545
Published: April 8, 2019
An
unprecedented
cascade
reaction
of
benzoyl
sulfoxonium
ylides
with
α-diazocarbonyl
compounds
leading
to
the
formation
highly
functionalized
naphthalenones
containing
a
β-ketosulfoxonium
ylide
moiety
is
presented.
Promisingly,
naphthalenone
derivative
thus
obtained
was
found
be
versatile
intermediate
toward
diversely
naphthalene
derivatives
including
substituted
1-naphthol,
2-hydroxynaphthalen-1(2H)-one,
naphthalen-1,2-dione,
and
2-(methylsulfinyl)naphthalen-1-ol.
Topics in Current Chemistry,
Journal Year:
2018,
Volume and Issue:
376(3)
Published: April 13, 2018
Traditionally
employed
in
the
synthesis
of
small
ring
systems
and
rearrangement
chemistry,
sulfur-based
ylides
occupy
a
unique
position
toolbox
synthetic
organic
chemist.
In
recent
years
number
pioneering
researchers
have
looked
to
expand
application
these
unorthodox
reagents
through
use
transition
metal
catalysis.
The
strength
flexibility
such
combination
been
shown
be
key
importance
developing
powerful
novel
methodologies.
This
chapter
summarises
developments
metal-catalysed
sulfonium/sulfoxonium
ylide
reactions,
as
well
providing
historical
perspective.
overviewing
successes
this
area,
authors
hope
encourage
others
into
growing
field.
Advanced Synthesis & Catalysis,
Journal Year:
2018,
Volume and Issue:
360(19), P. 3781 - 3787
Published: July 12, 2018
Abstract
A
highly
chem‐
and
regioselective
synthesis
of
diversely
substituted
benzo[
a
]carbazoles
indolo[2,1‐
]‐isoquinolines
through
Rh(III)‐catalyzed
cascade
reactions
2‐arylindoles
with
sulfoxonium
ylides
is
presented.
To
be
specific,
treatment
2‐arylindoles,
2‐arylindole‐3‐carbaldehydes,
2‐arylindole‐3‐carbonitriles
or
2‐aryl‐3‐methylindoles
under
the
catalysis
Rh(III)
led
to
selective
formation
6‐aryl/alkyl
]carbazoles,
5‐acylbenzo[
6‐amino‐5‐acylbenzo[
12‐methylindolo[2,1‐
]isoquinolines,
respectively.
Mechanistically,
title
compounds
involves
process
including
metalation
inert
C(
sp
2
)−H
bond,
migratory
insertion
ylide
into
carbon‐metal
bond
via
an
in
situ
carbenoid
formation,
protodemetalation,
condensation.
our
knowledge,
this
first
example
which
β‐carbonyl
were
used
as
stable
carbene
precursors
bifunctional
C2
synthons
afford
]isoquinolines.
magnified
image
