European Journal of Organic Chemistry,
Journal Year:
2022,
Volume and Issue:
2022(43)
Published: Oct. 21, 2022
Abstract
The
hydroxyl‐directed
iridium‐catalyzed
peri
‐selective
C−H
bond
activation
to
synthesize
substituted
pyrano[2,3,4‐
de
]chromen‐2‐ones
and
further
chalcogenylation
under
blue
light
irradiation
has
been
realized
efficiently.
Most
products
of
polycyclic
pyrans
corresponding
chalcogenated
derivatives
with
various
substituents
were
achieved
in
good
excellent
yields.
Preliminary
mechanistic
studies
suggest
that
this
transformation
may
pass
through
a
five‐membered
iridacycle
intermediate
containing
an
O−Ir
σ‐bond
photocatalytic
free
radical
process.
Chemical Science,
Journal Year:
2021,
Volume and Issue:
13(5), P. 1192 - 1209
Published: Dec. 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
ACS Catalysis,
Journal Year:
2022,
Volume and Issue:
12(4), P. 2330 - 2347
Published: Feb. 1, 2022
Transition-metal-catalyzed
alkylation
of
(hetero)arenes
with
three-membered
carbo-/heterocycles
involving
C–H
activation
and
ring
scission
has
been
greatly
developed
over
the
past
few
years.
The
chelation-assisted
strategies
for
controlling
reactivity
site
selectivity
in
these
protocols
include
use
nitrogen-containing
directing
groups,
pre-existing
functional
a
Catellani-type
intermediate,
thereby
providing
rapid
access
to
numerous
oxygen-
or
heterocyclic
systems.
This
review
gives
an
update
area
various
catalytic
methodologies
applications
total
synthesis
natural
products
rings
as
alkylating
reagents,
which
are
classified
into
following
three
categories
on
basis
employed
strategies:
(i)
directed
by
(ii)
(iii)
aryl-NBE
intermediates
(Catellani-type
cascade
reaction).
Organic Letters,
Journal Year:
2022,
Volume and Issue:
24(40), P. 7288 - 7293
Published: Oct. 4, 2022
A
ruthenium-catalyzed
peri-selective
C-H
activation
and
annulation
of
1-naphthols
with
CF3-substituted
imidoyl
sulfoxonium
ylides
that
uses
hydroxyl
as
a
weakly
coordinating
directing
group
is
disclosed.
The
strategy
provides
facile
practical
route
to
diverse
trifluoromethyl-containing
2,3-dihydrobenzo[de]chromen-2-amines
high
efficiency.
Notable
advantages
this
protocol
include
readily
available
materials,
excellent
regioselectivity,
good
functional
compatibility,
scalability.
Organic Letters,
Journal Year:
2023,
Volume and Issue:
25(1), P. 215 - 219
Published: Jan. 3, 2023
An
unprecedented
annulation
reaction
is
developed
for
the
synthesis
of
dihydrofuran-fused
compounds.
In
this
Ru-catalyzed
hydroxyl-group-directed
reaction,
easily
affordable
sulfoxonium
ylides
and
1,4-dioxane
were
used
as
annulating
partners.
This
first
example
use
a
methylene
source
to
construct
heterocyclic
scaffold.
A
wide
range
dihydrofuran0fused
coumarins
naphthalenes
synthesized
using
three-component
reaction.
The Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
88(9), P. 5572 - 5585
Published: April 21, 2023
Organoselenium
compounds
are
important
scaffolds
in
pharmaceutical
molecules.
Herein,
we
report
metal-free,
electrochemical,
highly
chemo-
and
regioselective
synthesis
of
gem-diselenides
through
the
coupling
α-keto
sulfoxonium
ylides
with
diselenides.
The
versatility
electrochemical
manifold
enabled
selenylation
ample
scope
broad
functional
group
tolerance,
as
well
setting
stage
for
modification
complex
bioactive
Detailed
mechanistic
studies
revealed
that
key
C-Se
bond
was
constructed
using
n-Bu4NI
an
electrolyte
catalyst
electrosynthetic
protocol.
Finally,
desired
showed
excellent
antimicrobial
activity
against
Candida
albicans,
which
can
be
identified
lead
further
exploration.
Organic & Biomolecular Chemistry,
Journal Year:
2022,
Volume and Issue:
21(5), P. 879 - 909
Published: Dec. 6, 2022
Transition
metal-catalyzed
cross-coupling
of
sp2
C-H
bonds
with
diazo
compounds
via
carbene
migratory
insertion
represents
an
efficient
strategy
for
the
construction
C-C
and
C-heteroatom
in
organic
synthesis.
Despite
popularity
as
coupling
partners
activation,
they
pose
serious
safety
stability
issues
due
to
potential
exothermic
reactions
linked
release
N2
gas.
However,
compared
compounds,
sulfoxonium
ylides
are
generally
crystalline
solids,
more
stable,
widely
used
industrial
scales,
easier/safer
prepare.
Therefore,
recent
years
have
witnessed
upsurge
employing
α-carbonyl
alternative
surrogate
transition
activation.
Unlike
contain
inherent
serve
a
partner
well
weak
directing
group.
This
review
will
summarize
progress
made
both
categories
reactions.
Organic Letters,
Journal Year:
2025,
Volume and Issue:
unknown
Published: April 24, 2025
Herein,
we
report
a
novel
ligand-switchable
Pd-catalyzed
carbene
coupling
reaction
employing
vinylethylene
carbonates
and
sulfoxonium
ylides.
By
proper
choice
of
ligands,
the
chemoselectivity
process
could
be
efficiently
regulated,
allowing
for
availability
dihydrofuran
or
dienol
scaffolds.
This
method
features
mild
conditions,
broad
scope,
remarkable
synthetic
utility.
Compound
6f
can
effectively
stimulate
secretion
GLP-1,
providing
promising
insight
into
development
small-molecule
agonists
GLP-1
receptor.
The Journal of Organic Chemistry,
Journal Year:
2022,
Volume and Issue:
87(21), P. 14809 - 14818
Published: Oct. 26, 2022
A
one-pot
three-component
synthesis
of
multifunctionalized
isoquinolones
from
2-oxazolines,
iodonium
ylides,
and
carboxylic
acids
via
Rh(III)-catalyzed
oxazolinyl-directed
C-H
activation
tandem
annulation
under
redox-neutral
conditions
has
been
developed.
This
catalytic
system
is
characterized
by
readily
available
starting
materials,
a
wide
tolerance
functional
groups,
short
reaction
time,
high
yields.
The
synthetic
utility
the
cascade
was
further
demonstrated
gram-scale
derivatization
obtained
products.
Advanced Synthesis & Catalysis,
Journal Year:
2023,
Volume and Issue:
365(15), P. 2588 - 2593
Published: July 12, 2023
Abstract
A
concise
and
flexible
protocol
to
assemble
structurally
diverse
1
H
‐pyrrolo[3,4‐
b
]quinoline‐1,3(2
)‐diones
(29
examples,
70–87%
yields)
has
been
developed
via
one‐pot
stepwise
synthesis.
The
potentially
valuable
quinine‐fused
heterocycles
were
synthetized
by
utilizing
aliphatic
alcohol
hydroxyl
as
directing
group
which
promoted
a
sequential
transformation
form
functionalized
aminomaleimides,
then
underwent
an
I
2
‐oxidized
tandem
annulations.
This
route
involved
the
formation
of
multiple
new
chemical
bonds
(C=N,
2C−N,
C−C)
in
fashion
under
mild
conditions.
Organic Chemistry Frontiers,
Journal Year:
2022,
Volume and Issue:
9(20), P. 5617 - 5623
Published: Jan. 1, 2022
A
method
for
the
synthesis
of
6-alkenylindazolo[3,2-a]isoquinolines
via
Rh(
iii
)-catalysed
C–H
bond
activation/cyclization
has
been
developed.
The
title
products
exhibited
favourable
fluorescence
properties
which
were
verified
by
relevant
experiments.
