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
Catalytic 1,1-diazidation of alkenes
Nature Communications,
Год журнала:
2024,
Номер
15(1)
Опубликована: Апрель 29, 2024
Compared
to
well-developed
catalytic
1,2-diazidation
of
alkenes
produce
vicinal
diazides,
the
corresponding
1,1-diazidation
yield
geminal
diazides
has
not
been
realized.
Here
we
report
an
efficient
approach
for
by
redox-active
selenium
catalysis.
Under
mild
conditions,
electron-rich
aryl
with
Z
or
E
Z/E
mixed
configuration
can
undergo
migratory
give
a
series
functionalized
monoalkyl
dialkyl
that
are
difficult
access
other
methods.
The
method
is
also
effective
construction
polydiazides.
formed
relatively
safe
TGA-DSC
analysis
and
impact
sensitivity
tests,
be
easily
converted
into
various
valuable
molecules.
In
addition,
interesting
reactivity
molecules
via
diazidomethyl
moiety
as
formal
leaving
group
in
presence
Lewis
acid
disclosed.
Mechanistic
studies
revealed
selenenylation-deselenenylation
followed
1,2-aryl
migration
process
involved
reactions,
which
provides
basis
design
new
reactions.
Язык: Английский
Gem-difluorinative ring-expansion of alkenes
Опубликована: Апрель 18, 2024
Incorporating
fluorine
into
aliphatic
rings
induces
significant
alterations
in
molecular
conformation,
acidity/basicity,
and
lipophilicity.
Current
methods
for
synthesizing
fluorinated
rings,
however,
involve
manipulating
functional
groups
within
pre-existing
ring
systems.
Here,
we
have
developed
a
novel
chemical
reaction
-
gem-difluorinative
ring-expansion
of
methylenecycloalkanes.
The
involves
iodine(III)
species,
allows
the
preparation
gem-difluorinated
macrocyclic,
fused,
spiro,
bridged,
natural
product-derived
structures.
protocol's
practicality
is
demonstrated
through
several
decagram-scale
syntheses.
Язык: Английский
Hypervalent Iodine Mediated Ring-Opening 1,3-Difluorination of Benzylidenecyclopropanes
Long-Ling Huang,
Jiayi Li,
Qigang Sun
и другие.
Synthesis,
Год журнала:
2024,
Номер
unknown
Опубликована: Июль 25, 2024
Abstract
1,3-Difluorinated
compounds
are
characterized
by
their
unique
conformation,
influenced
1,3-dipolar
minimization
effects.
However,
synthetic
methods
relatively
limited.
Here,
a
ring-opening
1,3-difluorination
of
benzylidenecyclopropanes
(BCPs)
using
HF·Py,
mediated
an
electron-poor
hypervalent
iodine
reagent,
which
is
generated
in
situ
the
oxidation
o-nitroiodobenzene
with
mCPBA
described.
The
protocol
features
mild
reaction
conditions,
good
functional
group
tolerance,
and
moderate
to
yields.
Additionally,
utility
this
method
showcased
further
transformations
olefin
allylic
fluoride
motif.
Язык: Английский
Straightforward Synthesis of 1‐Aryloxy‐1,1‐difluoro‐3‐aminopropan‐2‐ols – Accessing Fluorinated Derivatives of Commercialized Beta‐Blockers
European Journal of Organic Chemistry,
Год журнала:
2024,
Номер
unknown
Опубликована: Май 24, 2024
Abstract
The
efficient
synthesis
of
an
array
1‐aryloxy‐1,1‐difluoro‐3‐aminopropan‐2‐ols
in
a
one‐pot
epoxidation/nucleophilic
ring‐opening
via
the
corresponding
iodohydrines
is
described.
This
methodology
permits
construction
1,1‐difluorinated
derivatives
commercialized
beta‐blockers
addition
to
unprecedented
members
this
compound
class.
Язык: Английский
1.7 Synthesis of Difluoromethylene-Containing Compounds
Опубликована: Янв. 1, 2024
Abstract
The
difluoromethylene
group
(CF2)
is
a
valuable
fluorinated
motif
that
widely
present
in
pharmaceuticals,
agrochemicals,
and
advanced
functional
materials
because
of
the
unique
properties
fluorine
atoms.
Consequently,
considerable
efforts
have
been
dedicated
to
introducing
into
organic
molecules.
This
review
summarizes
progress
synthesis
difunctionalized
difluoromethane
(R1−CF2−FG)
compounds,
including
methods
for
difluoroalkylation
C—X
unsaturated
bonds,
gem-difluorination
reactions.
Язык: Английский