The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(17), С. 12263 - 12276
Опубликована: Авг. 15, 2024
A
fast,
scalable,
transition
metal-free,
electrochemical
sp2
geminal
functionalization
of
carbonyls
enabled
by
anodic
oxidation
non-prefunctionalized
chromone-fused
indolizines
to
access
the
triarylmethanes
(TRAMs)
is
disclosed
for
first
time.
This
momentary
approach
features
use
readily
available
carbonyls,
implantation
C(sp3)
center
(well-known
dramatically
improving
biological
active
potency),
a
broad
substrate
scope,
and
excellent
yields
TRAMs
with
fluorescence
properties.
Acta Chimica Sinica,
Год журнала:
2023,
Номер
81(7), С. 793 - 793
Опубликована: Янв. 1, 2023
o-Hydroxyphenyl
substituted
p-quinone
methides
(p-QMs)
belong
to
a
class
of
p-QMs
with
unique
advantages.They
not
only
maintain
the
high
reactivity
p-QMs,
but
also
have
more
reactive
and
activation
sites
owing
introduction
hydroxyl
group.Therefore,
o-hydroxyphenyl
wide
applications
in
synthetic
medicinal
chemistry.The
catalytic
asymmetric
1,6-conjugate
addition
[4＋n]
cycloaddition
developed
very
rapidly
recent
years,
which
become
efficient
strategies
for
synthesis
chiral
oxygen-containing
heterocycles
arylmethanes
potential
bioactivity.This
review
summarizes
reactions
involving
points
out
remaining
challenges
this
research
area,
will
open
new
window
design
type
their
involved
reactions.
Abstract
The
efficient
synthesis
of
chiral
2,2‐disubstituted
indolin‐3‐ones
is
great
importance
due
to
its
significant
synthetic
and
biological
applications.
However,
catalytic
enantioselective
methods
for
de
novo
such
heterocycles
remain
scarce.
Herein,
a
novel
cyclizative
rearrangement
readily
available
anilines
vicinal
diketones
the
one‐step
construction
enantioenriched
presented.
reaction
proceeds
through
self‐sorted
[3+2]
heteroannulation/regioselective
dehydration/1,2‐ester
shift
process.
Only
phosphoric
acid
employed
promote
entire
sequence
simplify
manipulation
this
protocol.
Various
common
aniline
derivatives
are
successfully
applied
asymmetric
as
1,3‐binuclephiles
first
time.
Remarkably,
observed
stereoselectivity
proposed
originate
from
an
amine‐directed
regio‐
ortho
‐Csp
2
‐H
addition
ketones.
A
range
transformations
resulting
products
demonstrated
well.
Organic Letters,
Год журнала:
2023,
Номер
25(22), С. 4000 - 4004
Опубликована: Май 30, 2023
Rhodium-catalyzed
C-H
functionalization
of
cyclohexadiene
derivatives
with
diaryldiazomethanes
followed
by
oxidation
DDQ
provides
ready
access
to
triarylmethanes.
Two
chiral
dirhodium
tetracarboxylates,
Rh2(S-PTAD)4
and
Rh2(S-TPPTTL)4,
were
found
be
the
optimum
catalysts
for
these
transformations.
This
method
showcases
ability
perform
intermolecular
insertion
high
enantioselectivity
good
yields.
The
has
a
broad
substrate
scope,
leading
triarylmethane
products
variety
aryl
heteroaryl
substituents,
including
benzofuran
pyridine
heterocycles.
Chemical Reviews,
Год журнала:
2025,
Номер
unknown
Опубликована: Март 18, 2025
Chiral
phosphoric
acids
(CPAs)
have
emerged
as
highly
effective
Brønsted
acid
catalysts
in
an
expanding
range
of
asymmetric
transformations,
often
through
novel
multifunctional
substrate
activation
modes.
Versatile
and
broadly
appealing,
these
benefit
from
modular
tunable
structures,
compatibility
with
additives.
Given
the
unique
types
noncovalent
interactions
(NCIs)
that
can
be
established
between
CPAs
various
reactants─such
hydrogen
bonding,
aromatic
interactions,
van
der
Waals
forces─it
is
unsurprising
catalyst
systems
become
a
promising
approach
for
accessing
diverse
chiral
product
outcomes.
This
review
aims
to
provide
in-depth
exploration
mechanisms
by
which
impart
stereoselectivity,
positioning
NCIs
central
feature
connects
broad
spectrum
catalytic
reactions.
Spanning
literature
2004
2024,
it
covers
nucleophilic
additions,
radical
atroposelective
bond
formations,
highlighting
applicability
CPA
organocatalysis.
Special
emphasis
placed
on
structural
mechanistic
features
govern
CPA-substrate
well
tools
techniques
developed
enhance
our
understanding
their
behavior.
In
addition
emphasizing
details
stereocontrolling
elements
individual
reactions,
we
carefully
structured
this
natural
progression
specifics
broader,
class-level
perspective.
Overall,
findings
underscore
critical
role
catalysis
significant
contributions
advancing
synthesis.
Organic Chemistry Frontiers,
Год журнала:
2023,
Номер
10(20), С. 5274 - 5283
Опубликована: Янв. 1, 2023
The
asymmetric
Friedel–Crafts
alkylation
of
3-bromo-3-substituted
oxindoles
with
arenes
and
heteroarenes
was
achieved
to
synthesize
enantioenriched
C3-arylated
oxindoles.
The Journal of Organic Chemistry,
Год журнала:
2023,
Номер
88(16), С. 11778 - 11792
Опубликована: Авг. 9, 2023
An
efficient,
secondary
amine-catalyzed
cascade
annulation
of
2-O/N-propargylarylaldehydes
with
2,6-dialkylphenols
was
established
to
access
biologically
relevant
functionalized
2H-chromenes
and
1,2-dihydroquinolines
tethered
a
synthetically
useful
p-quinone
methide
scaffold
in
high
yields
under
microwave
irradiation
conventional
heating
conditions.
The
microwave-assisted
strategy
convenient,
clean,
rapid,
yielding
which
the
reactions
were
completed
just
15
min,
obtained
up
95%.
This
highly
atom-economical
domino
process
constructed
two
new
C-C
double
bonds
six-membered
O/N-heterocyclic
ring
single
synthetic
operation.
Its
mechanism
rationalized
as
involving
sequential
iminium
ion
formation,
nucleophilic
addition,
intramolecular
steps.
Furthermore,
synthesized
2H-chromene
derivatives
transformed
into
valuable
indeno[2,1-c]chromenes,
5H-indeno[2,1-c]quinolines,
oxireno[2,3-c]chromene
via
palladium-catalyzed
C-H
bond
activation
epoxidation,
respectively.
Advanced Synthesis & Catalysis,
Год журнала:
2023,
Номер
366(4), С. 774 - 779
Опубликована: Окт. 26, 2023
Abstract
Rh‐catalyzed
asymmetric
C(
sp
3
)−H
arylation
of
8‐benzylquinolines
with
arylboronic
acids
was
developed.
In
the
presence
5
mol%
BINOL‐derived
chiral
cyclopentadienyl
rhodium
complex,
benzylic
bond
reaction
proceeded
smoothly
to
afford
a
series
enantioenriched
triarylmethanes
in
moderate
good
yields
excellent
enantioselective
control
(24–89%
yields,
63–93%
ee).
The
method
displays
broad
substrate
scope
and
functional
group
tolerance
under
mild
conditions.
Organic & Biomolecular Chemistry,
Год журнала:
2024,
Номер
22(11), С. 2187 - 2191
Опубликована: Янв. 1, 2024
Herein,
we
developed
an
efficient
HOTf-promoted
Friedel–Crafts
alkylation
reaction
of
broad
arenes
with
α-aryl-α-diazoesters
under
metal-free
and
solvent-free
conditions.
