Sustainable and scalable one-pot synthesis of diaryliodonium salts
Sayad Doobary,
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Leonard Kersting,
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Piret Villo
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et al.
Chemical Communications,
Journal Year:
2025,
Volume and Issue:
unknown
Published: Jan. 1, 2025
Two
one-pot
syntheses
of
diaryliodonium
triflates
are
presented,
rendering
the
production
these
electrophilic
arylating
agents
more
sustainable.
Language: Английский
Arylation of Diethyl Acetamidomalonate with Diaryliodonium Salts En Route to α-Arylglycines
Dmitry I. Bugaenko,
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Olga A. Tikhanova,
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Valeriy V. Andreychev
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et al.
The Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
89(14), P. 9923 - 9928
Published: July 1, 2024
Diethyl
acetamidomalonate
(DEAM)
has
been
widely
used
for
the
synthesis
of
α-amino
acids
via
C-alkylation
under
basic
conditions
followed
by
hydrolysis/decarboxylation.
In
contrast,
C-arylation
this
reagent
remains
undeveloped.
Herein,
we
report
a
novel
strategy
racemic
α-arylglycines
based
on
selective
arylation
DEAM
with
diaryliodonium
salts
mild,
transition
metal-free
conditions.
The
reaction
features
good
functional
group
tolerance
and
easy
scalability
is
applicable
to
chemoselective
C-H-modification
arenes
including
approved
drugs,
thus
enabling
straightforward
approach
complex
that
would
be
challenging
make
otherwise.
Language: Английский
Synthesis of Diaryl Ethers via Hypervalent Iodine-Mediated C–H Functionalization
Chenghu Hu,
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Qi Jia,
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Wenjing Bao
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et al.
Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(37), P. 7864 - 7868
Published: Sept. 9, 2024
A
hypervalent
iodine-reagent-based
C-H
functionalization
strategy
was
utilized
to
synthesize
diaryl
ethers.
This
method
directly
transforms
various
arenes
into
their
corresponding
diaryliodonium
salts,
followed
by
a
C-O
coupling
reaction
produce
structurally
diverse
The
efficacy
of
this
approach
in
the
late-stage
structural
modifications
complex
molecules
demonstrated.
Language: Английский
Iodonium(III) Ylide: An Iodoalkylation Reagent with Aryne
Weigang Xu,
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Pengfei Li,
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Yuerong Li
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et al.
The Journal of Organic Chemistry,
Journal Year:
2025,
Volume and Issue:
unknown
Published: Feb. 5, 2025
A
tandem
Hexadehydro-Diels–Alder
(HDDA)/[2
+
2]
cycloaddition/aryl
migration
reaction
of
iodonium
ylide
with
tetrayne
is
described,
in
which
served
as
a
unique
double
bond
and
reacted
aryne
to
form
four-membered
iodonium(III)
cycle,
then
converted
iodoarene
after
aryl
group
from
iodine
adjacent
carbon.
This
strategy
allows
the
efficient
construction
fully
substituted
compounds.
Language: Английский
Synthesis of 1,2-Disubstituted-3-thioindoles by the Madelung Reaction
Russian Journal of Organic Chemistry,
Journal Year:
2025,
Volume and Issue:
61(2), P. 217 - 224
Published: Feb. 1, 2025
Language: Английский
Hypervalent Iodine-Mediated Selective Monofunctionalization of Calix[4]arenes
Haoliang Hao,
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Wei Zhang,
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Wenjie Zhu
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et al.
Organic Letters,
Journal Year:
2025,
Volume and Issue:
unknown
Published: April 30, 2025
The
selective
introduction
of
a
single
functionality
on
the
upper
rim
calix[4]arene
is
challenging
due
to
identical
reactivity
its
four
aryl
units.
In
this
study,
we
introduce
novel
strategy
for
monofunctional
modification
calix[4]arenes
using
hypervalent
iodine-mediated
C-H
functionalization.
This
process
yields
calix[4]arene-iodonium
salt,
which
can
be
easily
isolated
distinct
solubility
compared
native
calixarene.
versatile
intermediate
efficiently
undergoes
C-O,
C-N,
and
C-S
couplings
with
variety
nucleophiles,
including
amines,
phenols,
thiols,
sulfinate
salts
under
mild
conditions.
enables
streamlined
structural
diversification
calix[4]arenes,
opening
new
avenues
design
supramolecular
macrocycles
tailored
functions.
Language: Английский
Site-Selective Nitration of Arene via Hypervalent Iodine-Mediated C–H Functionalization
Ziyang Zhang,
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Wenjing Bao,
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Guangxing Gu
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et al.
Organic Letters,
Journal Year:
2025,
Volume and Issue:
unknown
Published: May 7, 2025
We
developed
a
novel
nitration
method
using
hypervalent
iodine
for
site-selective
C-H
functionalization.
This
technique
efficiently
synthesizes
nitroarenes
with
high
regioselectivity
and
is
scalable,
enhancing
the
late-stage
modification
of
bioactive
pharmaceuticals.
Language: Английский
Interrupted Plancher Rearrangement Initiated by Dearomative Epoxide–Indole Cyclization: Formal Umpolung Reactivity of Indoles
Raju Chouhan,
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Sajal Kumar Das
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Organic Letters,
Journal Year:
2024,
Volume and Issue:
unknown
Published: Dec. 12, 2024
We
herein
report
the
serendipitous
discovery
of
interrupted
Plancher
rearrangement
initiated
by
an
HFIP-promoted
dearomative
epoxide-indole
cyclization,
unlocking
a
new
blueprint
to
formal
C3
umpolung
reactivity
indoles.
This
rapid
complexity
generating
cascade
process
paves
way
toward
class
fused-bridged
indolines
in
high
yields
and
under
full
regio-
diastereocontrol.
The
reaction
is
amenable
wide
range
substituents
starting
materials.
Language: Английский
Copper-Catalyzed Cascade Cyclization of 2-Nitrochalcones with NH-Heterocycles
The Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
unknown
Published: Nov. 19, 2024
We
developed
a
method
for
allowing
cascade
cyclization
of
2-nitrochalcones
with
pyrazoles,
imidazole,
and
indazole
in
the
presence
CuI
catalyst,
DBU
base,
THF
solvent.
The
conditions
were
tolerant
an
array
useful
functionalities
including
ester,
nitro,
cyano,
halogen
groups.
A
mechanistic
consideration
was
also
provided,
as
H2O2
presumably
byproduct.
Our
appears
to
be
rare
example
directly
prepare
C3-heterocyclic
unprotected
indoles.
Language: Английский