European Journal of Organic Chemistry,
Journal Year:
2022,
Volume and Issue:
2022(34)
Published: July 29, 2022
Abstract
Herein,
a
method
for
N
‐aryl
amides
preparation
has
been
established
through
Rh(III)‐catalyzed
C(sp
2
)−N
cross‐coupling
reactions
of
alkyl
dioxazolones
with
arylboronic
acids,
heterocyclic
boronic
acid,
and
alkenyl
acid.
This
efficient
straightforward
catalytic
approach
was
featured
broad
substrate
scope
(38
examples),
good
functional
group
compatibility,
high
yields
(up
to
99
%),
is
suitable
late‐stage
modification
drug
molecular
structures.
The
possible
mechanism
hypothesis
also
accomplished.
Organic Letters,
Journal Year:
2023,
Volume and Issue:
25(23), P. 4286 - 4291
Published: June 2, 2023
Two
categories
of
tetrasubstituted
phenols
were
prepared
via
the
cycloaddition
reaction
vinyl
sulfoxonnium
ylides
with
cyclopropenones
in
a
switchable
manner.
Copper
carbenoid
was
proposed
as
active
intermediate
process
2,3,4,5-tetrasubstituted
formation,
while
2,3,5,6-tetrasubstituted
generated
direct
[3
+
3]
annulation
under
metal-free
conditions.
Further
synthetic
applications
also
demonstrated.
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 Chemistry Frontiers,
Journal Year:
2024,
Volume and Issue:
11(11), P. 3234 - 3241
Published: Jan. 1, 2024
Herein,
we
present
a
cascade
O–H
double
insertion
reaction
between
I
(III)
/S
(VI)
-ylides,
carboxylic
acids,
and
alcohols
under
metal-free
conditions,
enabling
the
modular
synthesis
of
unsymmetrical
α,α-
O
,
-substituted
ketones.
Advanced Synthesis & Catalysis,
Journal Year:
2024,
Volume and Issue:
366(8), P. 1744 - 1750
Published: Feb. 22, 2024
Abstract
The
transmetalation
triggered
rhodium‐catalyzed
C−H
bond
activation
and
tandem
annulation
of
2‐biphenylboronic
acids
with
sulfoxonium
ylides
or
iodonium
has
been
developed.
Various
products
phenanthrenes
were
constructed
under
redox‐neutral
conditions
in
34–86%
yields.
Several
mechanism
exploration
experiments
derivatization
reactions
conducted
sequence
to
gain
a
deeper
understanding
the
process
potential
this
transformation.
It
offers
an
alternative
approach
for
synthesis
phenanthrene
derivatives.
Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(11), P. 2249 - 2254
Published: March 7, 2024
A
copper-mediated
[3
+
2]
cyclization
of
CF3-imidoyl
sulfoxonium
ylides
and
terminal
alkynes
has
been
demonstrated.
This
work
provides
a
practical
approach
for
assembling
5-trifluoromethylpyrroles
with
the
merits
broad
substrate
scope,
good
functional
tolerance,
mild
reaction
conditions.
Control
experiments
DFT
studies
indicate
that
this
may
involve
addition
π-bonds
by
copper-carbene
radicals
hydrogen
migration.
Advanced Synthesis & Catalysis,
Journal Year:
2021,
Volume and Issue:
363(5), P. 1436 - 1442
Published: Jan. 21, 2021
Abstract
A
highly
efficient
cascade
Rh(III)‐catalyzed
C−H
activation/intramolecular
chemodivergent
cyclization
reaction
of
N‐carbamoylindoles
and
sulfoxonium
ylides
has
been
successfully
achieved
for
the
first
time.
This
synergistic
process
provides
rapid
access
to
functionalized
dihydropyrimidoindolone
tricyclic
[1,3]oxazino[3,4‐
a
]indol‐1‐ones
skeletons
under
redox
neutral
conditions
with
broad
substrate
scope
remarkable
functional‐group
compatibility.
Further
late‐stage
modification
structurally
complex
drug
molecules
mechanistic
studies
were
also
accomplished.
magnified
image
Organic Letters,
Journal Year:
2021,
Volume and Issue:
23(19), P. 7407 - 7411
Published: Sept. 20, 2021
A
lithium-bromide-promoted
nucleophilic
substitution/annulation
cascade
reaction
between
CF3-imidoyl
sulfoxonium
ylides
and
1,3-dicarbonyl
compounds
has
been
established,
the
corresponding
1,2,3-trisubstituted
5-trifluoromethylpyrroles
have
obtained
in
27–78%
yield.
This
features
a
broad
substrate
scope
generates
dimethyl
sulfoxide
H2O
as
byproducts.
Advanced Synthesis & Catalysis,
Journal Year:
2023,
Volume and Issue:
365(9), P. 1457 - 1464
Published: April 14, 2023
Abstract
In
this
study,
Rh(III)‐catalyzed
C−H
bifunctionalization
and
direct
vinylene
annulation
of
sulfoxonium
ylides
N
‐carbamoylindoles
with
carbonate
was
accomplished,
which
afforded
a
series
naphthalenones
containing
β‐ketosulfoxonium
ylide
moiety,
isocoumarins,
pyrimidones.
This
protocol
featured
mild
conditions,
broad
substrate
scope,
functional‐groups
compatibility.
addition,
related
applications
preliminary
mechanistic
exploratory
were
also
investigated
magnified
image
Advanced Synthesis & Catalysis,
Journal Year:
2020,
Volume and Issue:
363(2), P. 446 - 452
Published: Dec. 2, 2020
Abstract
A
formation
of
fused
tricyclic
[1,3]oxazino[3,4‐
a
]indol‐1‐ones
and
dihydropyrimido[1,6‐
]indol‐1(2
H
)‐ones
via
Rh(III)‐catalyzed
[3+3]
or
[4+2]
annulation
N
‐methoxy‐1
‐indole‐1‐carboxamides
with
sulfoxonium
ylides
has
been
developed.
These
selective
reactions
were
carried
out
by
switching
the
additives
notable
features
this
protocol
low
catalyst
loading
broad
substrate
scope
providing
corresponding
products
in
up
to
99%
yields.
magnified
image
