Angewandte Chemie,
Journal Year:
2023,
Volume and Issue:
135(29)
Published: March 31, 2023
Abstract
Benzothiophenes,
activated
by
oxidation
to
the
corresponding
S
‐oxides,
undergo
C−H/C−H‐type
coupling
with
phenols
give
C4
arylation
products.
While
an
electron‐withdrawing
group
at
C3
of
benzothiophene
is
important,
process
operates
without
a
directing
and
metal
catalyst,
thus
rendering
it
compatible
sensitive
functionalities—e.g.
halides
formyl
groups.
Quantum
chemical
calculations
suggest
formal
stepwise
mechanism
involving
heterolytic
cleavage
aryloxysulfur
species
π‐complex
phenoxonium
cation.
Subsequent
addition
cation
position
favored
over
C3;
Fukui
functions
predict
that
major
regioisomer
formed
more
electron‐rich
between
C4.
Varied
selective
manipulation
products
showcase
synthetic
utility
metal‐free
process.
Journal of the American Chemical Society,
Journal Year:
2025,
Volume and Issue:
unknown
Published: Jan. 8, 2025
The
asymmetric
and
divergent
total
syntheses
of
two
phragmalin
(moluccensins
G
H)
khayanolide-type
(krishnolide
F
khayseneganin
F)
limonoids
were
disclosed,
which
employed
a
torquoselective
interrupted
Nazarov
cyclization
as
the
key
step.
Taken
together
with
Liebeskind-Srogl
coupling,
benzoin
condensation,
bidirectional
acyloin
rearrangements,
our
strategy
would
simplify
synthetic
design
both
facilitate
their
modular
syntheses.
Moreover,
described
approach
also
provides
additional
insights
into
biosynthetic
relationships
between
these
distinct
skeletons.
Molecules,
Journal Year:
2023,
Volume and Issue:
28(2), P. 686 - 686
Published: Jan. 10, 2023
The
Nef
reaction
(nitro
to
carbonyl
group
conversion)
and
related
Meyer
are
among
the
key
transformations
of
aliphatic
nitro
compounds.
interrupted
versions
these
reactions
in
which
normal
pathway
is
redirected
a
different
end
product
by
an
external
nucleophile
much
less
common,
albeit
processes
substantially
increase
synthetic
potential
In
this
review,
examples
summarized,
prospects
methodology
diversity-oriented
organic
synthesis
analyzed.
bibliography
contains
90
references.
Angewandte Chemie International Edition,
Journal Year:
2023,
Volume and Issue:
62(29)
Published: March 31, 2023
Abstract
Benzothiophenes,
activated
by
oxidation
to
the
corresponding
S
‐oxides,
undergo
C−H/C−H‐type
coupling
with
phenols
give
C4
arylation
products.
While
an
electron‐withdrawing
group
at
C3
of
benzothiophene
is
important,
process
operates
without
a
directing
and
metal
catalyst,
thus
rendering
it
compatible
sensitive
functionalities—e.g.
halides
formyl
groups.
Quantum
chemical
calculations
suggest
formal
stepwise
mechanism
involving
heterolytic
cleavage
aryloxysulfur
species
π‐complex
phenoxonium
cation.
Subsequent
addition
cation
position
favored
over
C3;
Fukui
functions
predict
that
major
regioisomer
formed
more
electron‐rich
between
C4.
Varied
selective
manipulation
products
showcase
synthetic
utility
metal‐free
process.
Organic Letters,
Journal Year:
2025,
Volume and Issue:
unknown
Published: Feb. 17, 2025
Interrupted
reactions
redirect
established
processes,
often
resulting
in
unexpected
and
novel
outcomes.
By
employing
a
building
block
containing
both
acidic
oxo
functionalities
tethered
to
the
same
carbon,
we
uncovered
interrupted
variants
of
Ugi
Passerini
reactions.
More
than
20
derivatives
with
peptide-like
framework
have
been
synthesized,
demonstrating
broad
scope
versatility
these
Additional
studies
explored
use
various
nucleophiles
postmodifications
expand
even
more
chemical
diversity.
Chemistry - A European Journal,
Journal Year:
2024,
Volume and Issue:
30(20)
Published: Feb. 26, 2024
Abstract
The
particular
and
unique
mechanism
of
the
copper‐catalyzed
reaction
between
azides
alkynes
(CuAAC)
has
not
only
allowed
for
efficient
synthesis
1,2,3‐trisubstituted
1,4‐triazoles
in
excellent
yields
under
mild
conditions,
becoming
quintessential
click
reaction,
but
it
also
enabled
straightforward
formation
a
metallocycle
intermediate,
copper
triazolyl.
This,
suitable
conditions
able
to
suppress
its
protonolysis,
can
be
used
either
creation
new
bicyclic
triazolyl
structures
or
generation
novel
three
four‐component
reactions.
aim
this
review
is
rationalize
unify
all
these
transformations,
which
are
collectively
referred
as
“interrupted
reactions”.
Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(15), P. 3279 - 3283
Published: April 5, 2024
Chiral
spiro-polycyclic
oxindoles
are
valuable
heterocyclic
ring
systems
that
widely
distributed
in
natural
alkaloids
and
biologically
active
compounds.
Herein,
we
reported
an
asymmetric
tandem
Michael
addition/interrupted
Nef
reaction
of
nitromethane
with
oxindole-derived
alkenes
catalyzed
by
a
chiral
2-aminobenzimidazole
bifunctional
organocatalyst.
A
series
novel
enantiomerically
enriched
oxindole
derivatives
bearing
oxime
group
were
synthesized
moderate
to
excellent
isolated
yields
(up
99%)
level
enantioselectivities
99%
ee).
Furthermore,
the
antiproliferation
activity
resulting
evaluated,
compound
2d
demonstrated
promising
anticancer
properties
against
HCT116
(IC50
=
14.08
μM)
HT29
15.46
cell
lines.
ACS Central Science,
Journal Year:
2025,
Volume and Issue:
unknown
Published: April 10, 2025
A
multidisciplinary
platform
is
presented
to
address
aryl
hydrocarbon
receptor
(AhR)
modulation.
rewired
Yonemitsu
multicomponent
reaction
with
indole
2-carboxaldehydes
and
nucleophilic
species
was
designed
access
a
family
of
6-substituted
indolocarbazoles.
The
conformational
behavior
these
compounds
examined
rationalize
their
axial
chirality.
In
silico
docking
molecular
simulations
highlighted
key
features
implicated
in
binding
AhR.
Furthermore,
the
synthesis
linkable
derivatives
allowed
direct
development
conjugated
entities.
Reporter
gene
target
expression
analyses
identified
novel
structures
as
potent
noncytotoxic
activating
AhR
ligands,
that
can
be
extended
bifunctional
molecules.
anti-inflammatory
properties
agonists
were
assessed
interleukin-13
treated
keratinocytes.
Altogether,
synergistic
research
synthetic
computational
chemistry
integrated
biological
studies
opens
avenues
toward
understanding
roles
targeted
therapeutics.
