Recent Progress in Synthetic Applications of Hypervalent Iodine(III) Reagents
Chemical Reviews,
Год журнала:
2024,
Номер
unknown
Опубликована: Сен. 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.
Язык: Английский
Electrochemical Oxidative Dibrominative Cyclization of 1,n-Enynes with Hypervalent Iodoarene Intermediates Utilizing Recyclable Bromine Ionic Liquids
The Journal of Organic Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Апрель 5, 2025
An
electrochemical
approach
with
iodoarene
as
a
mediator
using
recyclable
ionic
liquids
to
achieve
dibromonative
cyclization
of
1,n-enynes
has
been
reported.
With
bromine
sources,
in
situ
generation
iodine(III)
compounds
through
oxidation
cyclization,
variety
heterocyclic
frameworks
containing
both
vinyl
and
alkyl
bromide
groups
had
obtained
high
yields
good
selectivity.
Язык: Английский
A decade of lessons in the activation of ArIL2 species
Chemical Science,
Год журнала:
2024,
Номер
15(11), С. 3784 - 3799
Опубликована: Янв. 1, 2024
Developments
in
methods
to
increase
the
oxidative
capacity
of
ArIL
2
reagents
are
discussed,
with
a
focus
on
an
understanding
these
species'
behaviour
from
perspective
iodine.
Язык: Английский
Reduced estrogenic risks of a sunscreen additive: Theoretical design and evaluation of functionally improved salicylates
Journal of Hazardous Materials,
Год журнала:
2024,
Номер
477, С. 135371 - 135371
Опубликована: Июль 29, 2024
Язык: Английский
Electrophilic activation of molecular bromine mediated by I(iii)
Dalton Transactions,
Год журнала:
2023,
Номер
52(44), С. 16472 - 16479
Опубликована: Янв. 1, 2023
In
pursuit
of
a
genuine
bromo-λ3-iodane,
it
has
been
found
that
the
combination
Br2
and
electron
deficient
λ3-iodanes
can
result
in
delivery
both
bromine
atoms
from
to
range
aryl
substrates,
some
highly
deactivated.
These
brominations
occur
rapidly
common
chlorinated
solvents
at
room
temperature
be
achieved
with
catalytic
activation
commercially
available
PhI(OAc)2
PhI(OTFA)2.
para-NO2
substituted
derivatives
are
employed
direct
bromination
towards
more
deactivated
substrates.
The
mechanism
is
discussed
insights
being
made,
however
remains
unclear.
Язык: Английский
ArI(NTf2)2: the boundary of oxidative capacity for ArIL2?
Chemical Communications,
Год журнала:
2023,
Номер
59(89), С. 13340 - 13343
Опубликована: Янв. 1, 2023
Synthesis
and
crystallographic
characterization
of
NO2-C6H4-I(NTf2)2
(NTf2
=
bistriflimide)
is
reported.
Experimental
results
find
that
this
compound
can
perform
oxidation
reactions
ArI(OTf)2
unable
to
theoretical
analysis
indicates
Ar-I(NTf2)2
the
most
oxidizing
in
ArIL2
class
compounds
known
may
also
be
practically
possible.
Язык: Английский
Structural verification and new reactivity for Stang's reagent, [PhI(CN)][OTf]
Dalton Transactions,
Год журнала:
2023,
Номер
52(25), С. 8536 - 8539
Опубликована: Янв. 1, 2023
The
structure
of
Stang's
reagent
[PhI(CN)][OTf]
is
confirmed
by
X-ray
crystallography
and
determined
to
be
best
described
as
an
ion-pair
in
organic
solution.
It
found
a
strong
Lewis
acid,
but
reaction
with
pyridine
ligands
gives
[Pyr-CN][OTf]
salts
via
oxidation
giving
new
derivative
the
CDAP
widely
used
activation
agent
for
polysaccharides.
Язык: Английский
Alkene versus Aryl Chlorination in Asymmetric Hypervalent Iodine Catalysis: A Case Study
Synlett,
Год журнала:
2023,
Номер
35(09), С. 1001 - 1006
Опубликована: Окт. 30, 2023
Abstract
Hypervalent
λ3-iodanes
have
become
a
prominent
tool
for
halofunctionalizations
of
alkenes.
Despite
many
examples
asymmetric
fluorinations
reported
lately,
the
corresponding
enantioselective
chlorination
reactions
using
iodoresorcinol-based
catalysts
are
significantly
less
developed,
with
only
one
example
known
to
date.
Here,
we
show
how
competing
aromatic
iodoarene
catalyst
is
significant
obstacle
in
these
transformations,
hinting
towards
conceptual
issue
this
well-established
class
chlorinations.
Consequently,
reaction
conditions
and
design
must
be
adapted
facilitate
an
effective
chirality
transfer.
Hence,
attention
should
paid
when
selecting
oxidizing
agent,
stoichiometry,
careful
analysis
conducted
identify
factual
catalytically
active
species.
Язык: Английский