Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(45), P. 9659 - 9664
Published: Oct. 31, 2024
1,3-Difunctionalization
of
donor–acceptor
cyclopropanes
with
copper
nitrate
and
N-halosuccinimide
was
developed
to
efficiently
afford
γ-halonitrates.
The
pivotal
factor
this
protocol
lies
in
the
dual
role
as
a
Lewis
acid
an
ideal
nitrooxy
source.
given
approach
features
easy
handling,
good
functional
group
compatibility,
wide
substrate
scope.
Furthermore,
various
transformations
obtained
γ-chloronitrates
underscore
remarkable
synthetic
potential
inherent
method.
Chemical Reviews,
Journal Year:
2024,
Volume and Issue:
unknown
Published: Sept. 13, 2024
Hypervalent
iodine(III)
compounds
have
found
wide
application
in
modern
organic
chemistry
as
environmentally
friendly
reagents
and
catalysts.
iodine
are
commonly
used
synthetically
important
halogenations,
oxidations,
aminations,
heterocyclizations,
various
oxidative
functionalizations
of
substrates.
Iodonium
salts
arylating
reagents,
while
iodonium
ylides
imides
excellent
carbene
nitrene
precursors.
Various
derivatives
benziodoxoles,
such
azidobenziodoxoles,
trifluoromethylbenziodoxoles,
alkynylbenziodoxoles,
alkenylbenziodoxoles
group
transfer
the
presence
transition
metal
catalysts,
under
metal-free
conditions,
or
using
photocatalysts
photoirradiation
conditions.
Development
hypervalent
catalytic
systems
discovery
highly
enantioselective
reactions
chiral
represent
a
particularly
recent
achievement
field
chemistry.
Chemical
transformations
promoted
by
many
cases
unique
cannot
be
performed
any
other
common,
non-iodine-based
reagent.
This
review
covers
literature
published
mainly
last
7-8
years,
between
2016
2024.
Nature Communications,
Journal Year:
2024,
Volume and Issue:
15(1)
Published: June 10, 2024
Chiral
1,2,3-triazoles
are
highly
attractive
motifs
in
various
fields.
However,
achieving
catalytic
asymmetric
click
reactions
of
azides
and
alkynes
for
chiral
triazole
synthesis
remains
a
significant
challenge,
mainly
due
to
the
limited
systems
substrate
scope.
Herein,
we
report
an
enantioselective
azidation/click
cascade
reaction
N-propargyl-β-ketoamides
with
readily
available
potent
azido
transfer
reagent
via
copper
catalysis,
which
affords
variety
up
99%
yield
95%
ee
under
mild
conditions.
Notably,
1,5-disubstituted
triazoles
that
have
not
been
accessed
by
previous
also
prepared
good
functional
group
tolerance.
The Journal of Organic Chemistry,
Journal Year:
2025,
Volume and Issue:
90(6), P. 2328 - 2340
Published: Jan. 31, 2025
A
benziodazole-type
O2NO-I(III)
compound
was
used
as
a
nitrating
reagent
to
react
with
series
of
electron-rich
arenes
including
substituted
phenols
and
anilines,
affording
the
corresponding
nitration
products
under
mild
conditions.
Mechanistically,
generates
reactive
nitrogen
dioxide
(NO2)
species,
which
enables
anilines.
The Journal of Organic Chemistry,
Journal Year:
2025,
Volume and Issue:
unknown
Published: March 6, 2025
We
describe
an
operationally
simple,
good-yielding,
two-step
cascade
process
to
convert
biscyclopropanes
1
into
high-value
benzocyclobutene
building
blocks
3.
This
study
highlights
the
novel
reactivity
of
our
"in-house"
donor-acceptor
cyclopropane,
achieving
complete
diastereoselectivity
and
regioselectivity
transfer.
Asian Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
13(4)
Published: Feb. 24, 2024
Abstract
A
catalyst‐free
intermolecular
dearomatization
reaction
of
β
‐naphthols
with
hypervalent‐iodine‐based
nitrooxylating
reagent
is
reported.
Various
nitrooxylated
‐naphthalenones
bearing
a
quaternary
carbon
stereogenic
center
were
obtained
smoothly
in
good
to
excellent
yields
(up
87
%)
under
mild
conditions.
This
method
features
conditions,
broad
substrate
scope
and
chemoselectivity.
Chemistry - A European Journal,
Journal Year:
2023,
Volume and Issue:
30(5)
Published: Oct. 17, 2023
Diazomethyl-substituted
iodine(III)
compounds
with
electron-withdrawing
groups
(EWG)
connected
to
diazo
methyl
center
were
a
type
of
donor-acceptor
potential
reaction
abilities
similar
ordinary
compounds.
Although
several
diazomethyl-substituted
synthesized
and
used
in
the
nucleophilic
substitution
reactions
as
early
1994,
synthesis
application
new
have
only
been
reported
certain
extent
recent
years.
In
presence
rhodium
catalyst,
photocatalyst,
or
nucleophiles,
can
be
converted
into
rhodium-carbenes,
diazomethyl
radicals,
ester
radicals
intermediates,
which
key
intermediates
for
formation
chemical
bonds.
The
aim
this
review
is
give
an
overview
organic
synthesis.
Communications Chemistry,
Journal Year:
2024,
Volume and Issue:
7(1)
Published: July 9, 2024
Abstract
The
existing
hypervalent
I(III)
reagents
bearing
ONO
2
group
are
limited
in
types
and
their
applications
primarily
focused
on
the
nitrooxylation
reactions
featuring
a
fully-
exo
fashion.
Herein,
benziodazole-type
O
NO-I(III)
compound
was
prepared
its
reaction
with
β-monosubstituted
enamines
presence
of
CuI
could
trigger
radical
nitration/cyclization/dehydration
cascade
to
provide
series
less
explored
but
biologically
interesting
furazan
heterocycles.
Mechanistically,
acts
as
nitrating
reagent
incorporates
NO
moiety
into
final
product
endo
model,
process
which
proposed
involve
nitration,
cyclization
dehydration.
Angewandte Chemie International Edition,
Journal Year:
2024,
Volume and Issue:
unknown
Published: Aug. 23, 2024
Abstract
Nitrate
esters
hold
pivotal
roles
in
pharmaceuticals,
energetic
materials,
and
atmospheric
processes,
motivating
the
development
of
efficient
synthesis
routes.
Here,
we
present
a
novel
catalytic
method
for
nitrates
via
direct
O
‐nitration
alcohols,
addressing
limitations
current
traditional
methods.
Leveraging
bench‐stable
recoverable
N
,6‐dinitrosaccharin
reagent,
our
strategy
employs
magnesium
triflate
to
achieve
mild
selective
offering
broad
substrate
scope
unprecedentedly
large
functional
group
tolerance
(e.g.
alkenes,
alkynes,
carbonyls).
DFT
mechanistic
studies
reveal
dual
role
catalyst
activation
both
nitrating
reagent
alcohol
substrate.
They
also
unveil
barrierless
proton
transfer
upon
formation
widely‐accepted
–
yet
elusive
solution
nitrooxonium
ion
intermediate.
Overall,
work
contributes
mild,
selective,
sustainable
approaches
synthesis,
with
potential
applications
drug
discovery,
materials
science,
environmental
chemistry.
Chemical Communications,
Journal Year:
2024,
Volume and Issue:
60(72), P. 9801 - 9804
Published: Jan. 1, 2024
A
metal-free
and
sustainable
visible-light-mediated
method
for
the
preparation
of
organic
nitrate
esters
has
been
developed
through
aerobic
nitrooxylation
reaction
α-diazoesters
cyclic
ethers
with
Nature Communications,
Journal Year:
2024,
Volume and Issue:
15(1)
Published: Aug. 20, 2024
Organic
nitrates,
as
effective
donors
of
the
signaling
molecule
nitric
oxide,
are
widely
applied
in
pharmaceutical
industry.
However,
practical
and
efficient
methods
for
accessing
organic
nitrates
still
scarce,
achieving
high
regiocontrol
unactivated
alkene
difunctionalization
remains
challenging.
Here
we
present
a
simple
method
highly
regioselective
halonitrooxylation
alkenes.
The
approach
utilizes
TMSX
(X:
Cl,
Br,
or
I)
oxybis(aryl-λ
