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
Mn(III) Catalyzed Cascade Cross-coupling / Annulation / C(O)-C Bond Insertion / Rearrangement: Access to Multi-substituted Indolenines in Water
Green Synthesis and Catalysis,
Год журнала:
2025,
Номер
unknown
Опубликована: Апрель 1, 2025
Язык: Английский
Synthesis of Closed‐Heterohelicenes Interconvertible between Their Monomeric and Dimeric Forms
Angewandte Chemie International Edition,
Год журнала:
2023,
Номер
62(50)
Опубликована: Окт. 26, 2023
Oxidative
fusion
reaction
of
cyclic
heteroaromatic
pentads
consisting
pyrrole
and
thiophene
gave
closed-heterohelicene
monomers
dimers
depending
on
the
oxidation
conditions.
Specifically,
with
[bis(trifluoroacetoxy)iodo]benzene
(PIFA)
closed-[7]helicene
connected
at
β-position
one
units
remarkably
elongated
C-C
bonds
about
1.60
Å.
Although
this
bond
was
intact
against
thermal
physical
activations,
homolytic
dissociation
took
place
in
DMSO
upon
irradiation
UV
light
to
give
corresponding
monomers.
Thus,
interconversion
between
closed-helicene
monomer
dimer
achieved.
The
optically
pure
photo-dissociated
into
associated
a
turn-on
circularly
polarized
luminescence
(CPL).
Язык: Английский
Synthesis of [4.6] Spirocarbocycles: A Base-promoted Ring-Expansion and Subsequent I2-mediated Regioselective Spirocyclization Protocol
Organic Chemistry Frontiers,
Год журнала:
2024,
Номер
11(23), С. 6797 - 6803
Опубликована: Янв. 1, 2024
An
efficient
protocol
for
the
synthesis
of
[4.6]
spirocarbocycles
by
reacting
cyclic
β-ketoesters
with
aryl-fused
1,6-diyn-3-ones
has
been
developed.
Язык: Английский
Hypervalent Iodine Catalyzed Cascade C–H Functionalization: An Atom‐Economical Strategy to Access Diverse 2‐Substituted Benzothiazoles
European Journal of Organic Chemistry,
Год журнала:
2024,
Номер
unknown
Опубликована: Окт. 10, 2024
Abstract
A
metal‐free
4,5‐difluoro‐2‐iodobenzoic
acid
catalyzed
C−H
functionalization
strategy
has
been
developed
for
the
synthesis
of
2‐(hetero)aryl
benzothiazoles
from
aryl
isothiocyanates
and
unfunctionalized
arenes/thiophenes/furans
at
room
temperature.
The
procedure
entails
one‐pot
cascade
carbon−carbon
carbon−sulfur
bond
formation
facilitated
by
triflic
acid,
which
serves
as
both
a
Brønsted
ligand
source
in
situ
generated
I(III)
center.
This
process
is
atom‐economical
offers
benefits
over
existing
protocols
synthesizing
terms
ease
use,
eco‐friendliness,
not
requiring
typical
use
aldehyde/carboxylic
precursors.
Mechanistic
studies
were
carried
out,
synthetic
utility
protocol
was
demonstrated
benzothiazole‐based
antitumor
drug
GW‐610.
Язык: Английский
Dearomative Spirocyclization of Ynamides
Chemical Science,
Год журнала:
2024,
Номер
15(45), С. 19136 - 19141
Опубликована: Янв. 1, 2024
Spiro
N-heterocycles,
particularly
aza-spiro
piperidines,
have
shown
significant
promise
in
pharmaceutical
applications
due
to
their
ability
enhance
physicochemical
properties.
Despite
potential,
the
preparation
of
these
complex
structures
poses
challenges.
To
address
this,
we
propose
a
one-pot
dearomative
spirocyclization
reaction
ynamides.
This
method
involves
copper-catalyzed
carbomagnesiation
reaction,
achieving
chemo-,
regio-,
and
stereoselective
formation
vinyl
metal
intermediates.
Upon
addition
Lewis
acid,
intermediates
undergo
regioselective
nucleophilic
dearomatization
event,
facilitating
synthesis
diverse
dihydropyridine
scaffolds
with
multiple
functional
handles.
Various
Grignard
reagents,
ynamides,
acylating
reagents
been
explored.
A
subsequent
hydrogenation
provides
access
both
partially
fully
reduced
spirocyclic
frameworks,
broadening
scope
potential
medicinal
applications.
Язык: Английский
Five-membered ring systems: Pyrroles and benzo analogs
Progress in heterocyclic chemistry,
Год журнала:
2024,
Номер
unknown, С. 123 - 173
Опубликована: Янв. 1, 2024
Язык: Английский
Synthesis of Closed‐Heterohelicenes Interconvertible between Their Monomeric and Dimeric Forms
Angewandte Chemie,
Год журнала:
2023,
Номер
135(50)
Опубликована: Окт. 26, 2023
Abstract
Oxidative
fusion
reaction
of
cyclic
heteroaromatic
pentads
consisting
pyrrole
and
thiophene
gave
closed‐heterohelicene
monomers
dimers
depending
on
the
oxidation
conditions.
Specifically,
with
[bis(trifluoroacetoxy)iodo]benzene
(PIFA)
closed‐[7]helicene
connected
at
β‐position
one
units
remarkably
elongated
C−C
bonds
about
1.60
Å.
Although
this
bond
was
intact
against
thermal
physical
activations,
homolytic
dissociation
took
place
in
DMSO
upon
irradiation
UV
light
to
give
corresponding
monomers.
Thus,
interconversion
between
closed‐helicene
monomer
dimer
achieved.
The
optically
pure
photo‐dissociated
into
associated
a
turn‐on
circularly
polarized
luminescence
(CPL).
Язык: Английский