Synlett,
Journal Year:
2024,
Volume and Issue:
unknown
Published: July 22, 2024
Abstract
A
novel
and
efficient
method
has
been
established
for
synthesizing
a
variety
of
heterotriarylmethanes
with
good
yields
by
employing
metal-free
self-coupling
reaction
benzofuran
azadienes.
The
involvement
t-BuONa
is
essential
in
this
process.
Remarkably,
technique
boasts
mild
conditions
exceptional
compatibility
various
functional
groups,
rendering
it
versatile
invaluable
asset
the
realm
organic
synthesis.
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.
Advanced Synthesis & Catalysis,
Journal Year:
2023,
Volume and Issue:
365(11), P. 1817 - 1823
Published: Feb. 7, 2023
Abstract
We
described
an
Rhodium(III)‐catalyzed
divergent
C−H
bond
functionalization
of
N
‐aryl
amidines
with
iodonium
ylides.
Carbazolones
and
zwitterionic
salts
were
diversely
constructed
through
intermolecular
annulation
intramolecular
proton
transfer
under
the
different
reaction
conditions.
This
protocol
is
operationally
simple
tolerates
a
variety
functional
groups.
The
efficient
post‐modification
pharmaceutical
molecules
demonstrates
its
practicability.
The Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
88(9), P. 5348 - 5358
Published: April 3, 2023
A
facile
access
to
isocoumarins
has
been
established
via
rhodium(III)-catalyzed
C-H
bond
activation
and
intramolecular
C-C
cascade
annulation
of
enaminones
cyclic
1,3-dicarbonyl
compounds.
The
synthetic
protocol
features
a
wide
range
substrates
with
high
functional
group
tolerance,
mild
reaction
conditions,
the
selective
cleavage
enaminone
bond.
Notably,
compounds
can
in
situ-generate
iodonium
ylide
as
carbene
precursor
prepare
polycyclic
scaffolds
by
reacting
PhI(OAc)2.
application
this
method
useful
precursors
bioactive
skeletons
is
also
exemplified.
The Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
88(13), P. 8360 - 8368
Published: June 1, 2023
A
1,2,3,5-tetrakis(carbazol-9-yl)-4,6-dicyanobenzene
(4-CzIPN)-photocatalyzed
cascade
arylation/cyclization
reaction
of
2-isocyanobiaryls
and
iodonium
ylides
was
established
for
the
synthesis
6-arylated
phenanthridines.
This
is
first
example
employing
as
aryl
radical
sources
in
a
visible-light-induced
cyclization
reaction.
The Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
89(3), P. 1753 - 1761
Published: Jan. 22, 2024
A
novel
and
flexible
domino
reaction
of
aurones
with
pyridin-2-yl
active
methylene
compounds
promoted
by
I2/BF3
has
been
developed
to
afford
spirodihydroindolizines
indolizines
in
a
controllable
manner.
When
the
was
performed
1,2-dichloroethane
at
80
°C,
variety
were
obtained,
whereas
it
almost
exclusively
provided
series
when
mixed
solvent
N,N-dimethylformamide
relatively
higher
temperature
100
°C.
Being
metal-free,
excellent
product
selectivity,
high
atom
economy,
good
functional
group
tolerance,
feasibility
for
large-scale
synthesis
are
salient
features
methodology.
Chemistry - A European Journal,
Journal Year:
2023,
Volume and Issue:
29(48)
Published: June 14, 2023
Generally,
the
potential
reactive
"olefin
pairs"
in
molecular
crystals
satisfying
Schmidt's
criteria
could
undergo
topological
[2+2]
cycloaddition.
In
this
study,
another
factor
that
affects
photodimerization
reactivity
of
chalcone
analogues
was
found.
The
cyclic
(E)-2-(2,4-dichlorobenzylidene)-2,3-dihydro-1H-inden-1-one
(BIO),
(E)-2-(naphthalen-2-ylmethylene)-2,3-dihydro-1H-inden-1-one
(NIO),
(Z)-2-(2,4-dichlorobenzylidene)benzofuran-3(2H)-one
(BFO),
and
(Z)-2-(2,4-dichlorobenzylidene)benzo[b]thiophen-3(2H)-one
(BTO)
have
been
synthesized.
While
geometrical
parameters
for
packing
above
four
compounds
did
not
exceed
criteria,
cycloaddition
occur
BIO
BTO.
single
crystal
structures
Hirshfeld
surface
analyses
revealed
interactions
C=O⋅⋅⋅H
(CH2
)
existed
between
adjacent
molecules
BIO.
Therefore,
carbonyl
methylene
groups
linked
with
one
carbon
atom
carbon-carbon
double
bond
were
tightly
confined
lattice,
acting
as
a
tweezer
to
inhibit
free
movement
suppressing
BTO,
similar
Cl⋅⋅⋅S
(C6
H4
prevented
bond.
contrast,
intermolecular
interaction
only
exists
around
group
BFO
NIO,
leaving
C=C
bonds
move
freely
allowing
occurrence
Driven
by
photodimerization,
needle-like
NIO
displayed
evident
photo-induced
bending
behavior.
This
work
demonstrates
affect
except
criteria.
These
findings
provide
valuable
insights
into
design
photomechanical
crystalline
materials.
The Journal of Organic Chemistry,
Journal Year:
2025,
Volume and Issue:
unknown
Published: March 21, 2025
Herein,
an
efficient
Rh-catalyzed
C-H
activation/annulation
between
α,β-unsaturated
amides
and
coumarin-derived
iodonium
ylides
has
been
developed,
affording
novel
pyrano[3,2-c]chromene-2,5-diones
analogues
in
high
yields.
Most
products
could
be
easily
isolated
by
precipitation
ethanol,
followed
simple
filtration.
Additionally,
this
protocol
demonstrated
the
benefits
of
environmentally
friendly
conditions,
air
compatibility,
good
functional
group
scale-up
synthesis
with
low
catalyst
loading,
a
recyclable
Rh
catalyst.
Importantly,
compounds
3m
3w
moderate
agonist
activity
on
TASK-3
channel,
I/I0
values
1.7650
±
0.1058
1.400
0.0589,
respectively.
RSC Advances,
Journal Year:
2025,
Volume and Issue:
15(14), P. 10634 - 10638
Published: Jan. 1, 2025
The
transition-metal-free
regioselective
[3
+
2]
annulation
of
azadienes
with
haloalcohols
for
the
preparation
highly
functionalized
spiro-oxazolidines
is
experimentally
simple,
broad
substrate
scope,
good
yields,
and
excellent
regioselectivity.
The Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
88(18), P. 13030 - 13041
Published: Aug. 30, 2023
A
novel
highly
regio-
and
diastereoselective
phosphine-catalyzed
[2
+
4]
annulation
of
benzofuran-derived
azadienes
(BDAs)
with
acidic
hydrogen-tethered
allyl
carbonates
has
been
developed
ingeniously.
range
functionalized
spiro[benzofuran-cyclohexane]
derivatives
two
consecutive
stereocenters
were
smoothly
obtained
in
moderate
to
excellent
yields
under
mild
reaction
conditions
from
readily
available
materials.
Moreover,
this
method
is
a
practical
scalable
strategy
that
creates
the
core
structural
motif
fungistatic
drug,
griseofulvin.
