A
variety
of
dearomatized
compounds
have
been
prepared
in
moderate
to
excellent
yields
from
planar
scaffolds
using
trichloroisocyanuric
acid
(TCCA)
as
an
atom-economical
chlorinating
agent.
The
method
tolerates
a
broad
range
functionalities
and
can
take
place
several
green
and/or
sustainable
solvents.
Twenty-one
examples
1,1-dichlorinated
products
2-naphthols
analogous
heteroarenes
(quinolinols,
isoquinolinols,
quinazolinol)
are
reported
along
with
five
monochlorinated
products.
utility
the
1,1-dichloronaphthalenone
product
reactive
intermediate
species
is
demonstrated
two-step,
one-pot
reaction
carried
out
solvent.
In
mechanistic
investigation,
coordination
agent
hydroxy
substituent
scaffold
prior
chlorine
transfer
implicated.
ACS Catalysis,
Journal Year:
2024,
Volume and Issue:
14(12), P. 9244 - 9253
Published: June 3, 2024
Catalytic
asymmetric
dearomatization
(CADA)
is
a
powerful
tool
for
the
rapid
construction
of
complex
chiral
three-dimensional
cyclic
molecules
featuring
quaternary
carbon
centers
from
readily
available
arenes.
However,
ubiquitous
nonfunctionalized
1-naphthols
to
afford
remains
challenging
and
undeveloped.
This
study
reports
dearomative
[4
+
1]
spiroannulation
via
copper
catalysis.
reaction
features
highly
chemo-,
regio-,
stereoselective
nucleophilic
addition
intramolecular
annulation
cascade
reactive
π-extended
copper-allenylidene,
thus
enabling
practical
synthesis
range
valuable
spirocyclic
enones
bearing
stereocenter
with
high
efficiency.
Furthermore,
this
protocol
applicable
phenols.
Control
experiments
supported
substitution-annulation
mechanism
by
excluding
process
involving
1,3-sigmatropic
shift.
Preliminary
biological
activity
studies
indicated
that
synthesized
hold
significant
promise
as
anticancer
agents
inducing
tumor
cell
apoptosis.
Asian Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
unknown
Published: June 27, 2024
Abstract
In
recent
years,
Morita‐Baylis‐Hillman
(MBH)
carbonates
have
been
extensively
used
in
domino
reactions
for
the
synthesis
of
novel
cyclic
and
acyclic
compounds.
This
review
highlights
progress
made
last
decade
a
series
compounds
from
an
uncyclized
reaction
or
annulation
MBH
carbonates,
which
demonstrates
that
excellent
reactivity
high
research
value
as
representative
substrates
organic
synthesis.
We
hope
summary
understanding
can
inspire
chemists
to
apply
these
design
more
efficient
reactions,
will
be
beneficial
drug
chemistry.
Advanced Synthesis & Catalysis,
Journal Year:
2024,
Volume and Issue:
366(20), P. 4238 - 4243
Published: March 16, 2024
Abstract
The
catalytic
asymmetric
dearomative
arylation
of
2‐naphthols
enabled
by
the
unconventional
reactivity
o
‐quinone
diimides,
i.
e.
1,4‐conjugate
addition
on
quinone
sp
2
hybridized
carbon,
has
been
established.
Under
catalysis
chiral
phosphoric
acid,
various
cyclohexaenones
bearing
an
all‐carbon
quaternary
stereocenter
have
prepared
with
excellent
yields
and
enantioselectivities.
Asian Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
13(4)
Published: Feb. 24, 2024
Abstract
A
catalyst‐free
intermolecular
dearomatization
reaction
of
β
‐naphthols
with
hypervalent‐iodine‐based
nitrooxylating
reagent
is
reported.
Various
nitrooxylated
‐naphthalenones
bearing
a
quaternary
carbon
stereogenic
center
were
obtained
smoothly
in
good
to
excellent
yields
(up
87
%)
under
mild
conditions.
This
method
features
conditions,
broad
substrate
scope
and
chemoselectivity.
Chemical Communications,
Journal Year:
2023,
Volume and Issue:
59(24), P. 3590 - 3593
Published: Jan. 1, 2023
An
asymmetric
allylic
dearomatization
reaction
of
1-nitro-2-naphthol
derivatives
with
Morita-Baylis-Hillman
(MBH)
adducts
has
been
developed.
By
utilizing
Pd
catalyst
derived
from
Pd(OAc)2
and
Trost
ligand
(R,R)-L1,
the
proceeded
smoothly
in
1,4-dioxane
at
room
temperature,
affording
substituted
β-naphthalenones
good
yields
(up
to
92%)
enantioselectivity
90%
ee).
A
range
1-nitro-2-naphthols
MBH
were
found
be
compatible
under
optimized
conditions.
This
provides
a
convenient
method
for
synthesis
enantioenriched
1-nitro-β-naphthalenone
derivatives.
Molecules,
Journal Year:
2024,
Volume and Issue:
29(5), P. 968 - 968
Published: Feb. 22, 2024
Since
the
discovery
of
classical
chiral
oxazoline
ferrocene
ligands
in
1995,
they
have
become
pivotal
transition
metal-catalyzed
asymmetric
transformations.
Over
past
decade,
a
notable
evolution
has
been
observed
with
emergence
siloxane-substituted
ferrocenes,
demonstrating
significant
potential
as
and
catalysts.
These
compounds
consistently
delivered
exceptional
results
diverse
mechanistically
distinct
transformations,
surpassing
capabilities
ligands.
This
review
meticulously
delineates
research
progress
on
compounds.
It
encompasses
synthesis
crucial
precursors
desired
products,
highlights
their
achievements
catalysis
reactions,
delves
into
exploration
derivatization
these
compounds,
emphasizing
introduction
ionophilic
groups
impact
recovery
metal
In
addition
to
presenting
current
state
knowledge,
this
propels
future
directions
by
identifying
topics
for
further
investigation
concerning
siloxane-tagged
derivatives.
derivatives
are
poised
be
promising
candidates
next
generation
highly
efficient
The Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
89(7), P. 4904 - 4915
Published: March 19, 2024
The
palladium-catalyzed
highly
regioselective
asymmetric
allylic
alkylation
of
3′-indolyl-3-oxindole
derivatives
with
Morita–Baylis–Hillman
(MBH)
carbonates
was
developed
to
facilely
construct
chiral
3,3′-bisindole
under
mild
reaction
conditions.
regioselectivity
(α/γ)
MBH
efficiently
switched
in
the
presence
oxalamide
phosphine
or
spiroketal-based
diphosphine/Pd(0)
complexes
as
a
catalyst.
A
series
multifunctional
all-carbon
quaternary
stereogenic
centers
were
obtained
high
yields
good
excellent
enantio-,
diastereo-,
and
regioselectivity.
present
process
is
endowed
some
salient
features
such
broad
substrate
scope,
N-protecting
group-free,
stereoselectivity,
well
adjustable
