Photoinduced C(sp3)−H Bicyclopentylation Enabled by an Electron Donor–Acceptor Complex‐Mediated Chemoselective Three‐Component Radical Relay
Angewandte Chemie International Edition,
Год журнала:
2024,
Номер
unknown
Опубликована: Апрель 10, 2024
The
photoredox
electron
donor-acceptor
(EDA)
complex-mediated
radical
coupling
reaction
has
gained
prominence
in
the
field
of
organic
synthesis,
finding
widespread
application
two-component
reactions.
However,
EDA
complex-promoted
multi-component
reactions
are
not
well
developed
with
only
a
limited
number
examples
have
been
reported.
Herein,
we
report
photoinduced
and
highly
chemoselective
three-component
arylalkylation
[1.1.1]propellane,
which
allows
direct
functionalization
C(sp
Язык: Английский
Seven-membered N-heterocycles as approved drugs and promising leads in medicinal chemistry as well as the metal-free domino access to their scaffolds
European Journal of Medicinal Chemistry,
Год журнала:
2024,
Номер
275, С. 116556 - 116556
Опубликована: Июнь 5, 2024
Azepanes
or
azepines
are
structural
motifs
of
many
drugs,
drug
candidates
and
evaluated
lead
compounds.
Even
though
compounds
having
N-heterocyclic
7-membered
rings
often
found
in
nature
(e.g.
alkaloids),
the
natural
this
group
rather
rare
as
approved
therapeutics.
Thus,
recently
studied
azepane
azepine-congeners
predominantly
consist
semi-synthetically
synthetically-obtained
scaffolds.
In
review
a
comparison
drugs
investigated
leads
was
proposed
taking
into
regard
their
aspects
(stereochemistry),
biological
activities,
pharmacokinetic
properties
confirmed
molecular
targets.
The
N-heterocycles
reveal
wide
range
not
only
against
CNS
diseases,
but
also
e.g.
antibacterial,
anticancer,
antiviral,
antiparasitic
allergy
agents.
As
most
potential
structures,
belonging
to
N-heterocycles,
synthetic
scaffolds,
report
reveals
different
efficient
metal-free
cascade
approaches
useful
synthesize
both
simple
azepine-containing
congeners
those
oligocyclic
structures.
Stereochemistry
azepane/azepine
fused
systems,
view
data
binding
with
targets,
is
discussed.
Apart
from
we
compare
advances
SAR
studies
(mainly
2018
2023),
whereas
related
part
concerning
various
domino
strategies
focused
on
last
ten
years.
Язык: Английский
Visible Light-Induced Radical Cascade Functionalization of Quinoxalin-2(1H)-ones: Three-Component 1,2-Di(hetero)arylation Approach with Styrenes and Thianthrenium Salts
Organic Letters,
Год журнала:
2024,
Номер
26(41), С. 8821 - 8826
Опубликована: Окт. 9, 2024
The
additive-free
visible
light-induced
three-component
1,2-di(hetero)arylation
of
styrenes
was
developed
using
quinoxalin-2(1
Язык: Английский
Photoinduced C(sp3)−H Bicyclopentylation Enabled by an Electron Donor–Acceptor Complex‐Mediated Chemoselective Three‐Component Radical Relay
Angewandte Chemie,
Год журнала:
2024,
Номер
136(39)
Опубликована: Апрель 10, 2024
Abstract
The
photoredox
electron
donor–acceptor
(EDA)
complex‐mediated
radical
coupling
reaction
has
gained
prominence
in
the
field
of
organic
synthesis,
finding
widespread
application
two‐component
reactions.
However,
EDA
complex‐promoted
multi‐component
reactions
are
not
well
developed
with
only
a
limited
number
examples
have
been
reported.
Herein,
we
report
photoinduced
and
highly
chemoselective
three‐component
arylalkylation
[1.1.1]propellane,
which
allows
direct
functionalization
C(sp
3
)−H
bicyclo[1.1.1]pentanes
(BCP)‐aryl
groups
under
mild
conditions.
A
variety
unnatural
α‐amino
acids,
featuring
structurally
diversified
1,3‐disubstituted
BCP
moieties,
were
synthesized
single‐step
process.
Notably,
leveraging
high
tension
release
unstable
transient
aryl
undergoes
rapid
conversion
into
relatively
stable
tertiary
alkyl
radical,
consequently,
competing
side‐reaction
was
entirely
suppressed.
strategic
use
this
approach
would
be
useful
for
design
diverse
It
is
noteworthy
that
late‐stage
incorporation
pharmacophores
peptides
achieved
both
liquid‐phase
solid‐phase
This
advancement
anticipated
to
significant
potential
future
development
peptide
drugs.
Язык: Английский
Photocatalytic Enantioselective Radical Cascade Multicomponent Minisci Reaction of β‐Carbolines Using Diazo Compounds as Radical Precursors
Advanced Science,
Год журнала:
2024,
Номер
11(25)
Опубликована: Апрель 19, 2024
Abstract
Here,
a
photocatalytic
asymmetric
multicomponent
cascade
Minisci
reaction
of
β‐carbolines
with
enamides
and
diazo
compounds
is
reported,
enabling
an
effective
enantioselective
radical
C─H
functionalization
high
yields
enantioselectivity
(up
to
83%
yield
95%
ee).
This
protocol
exhibits
step
economy,
chemo‐/enantio‐selective
control,
good
functional
group
tolerance,
allowing
access
variety
valuable
chiral
β‐carbolines.
Notably,
are
suitable
precursors
in
reactions.
Moreover,
the
efficiency
practicality
this
approach
demonstrated
by
synthesis
bioactive
natural
products.
Язык: Английский
A new dual nickel/ferrocenyl-chalcone as photoredox catalyst along with DFT studies for the three-component domino performance
Journal of Photochemistry and Photobiology A Chemistry,
Год журнала:
2024,
Номер
451, С. 115494 - 115494
Опубликована: Янв. 28, 2024
Язык: Английский
Photo(Multicomponent) Reaction of Quinoxalin‐2(1H)‐ones with CBrCl3 and Styrenes by Mes‐Acr‐MeClO4
Buddhadeb Pal,
Soumyashree Priyadarshinee,
Prasenjit Mal
и другие.
ChemCatChem,
Год журнала:
2024,
Номер
unknown
Опубликована: Окт. 30, 2024
Abstract
In
this
study,
we
explored
the
use
of
Mes‐Acr‐MeClO
4
as
a
visible
light
photocatalyst
for
multicomponent
reactions
involving
quinoxalin‐2(
1
H)‐ones
with
CBrCl
3
and
styrene.
The
method
showcases
regioselective
functionalization
in
three‐component
system,
forming
two
C─C
bonds
one
pot.
Mechanistic
investigations
suggest
radical‐mediated
pathway,
initiated
by
photoexcitation
,
followed
halogen
atom
abstraction
from
.
This
approach
provides
versatile
sustainable
route
H)‐one
functionalization,
effectively
facilitating
photocatalyzed
reaction
under
mild
conditions
irradiation,
yielding
high
selectivity
efficiency.
Язык: Английский
Visible Light-Mediated Four-Component synthesis of Polyfunctionalized pyrroles using Eosin-Y via the HAT process
Journal of Photochemistry and Photobiology A Chemistry,
Год журнала:
2024,
Номер
457, С. 115863 - 115863
Опубликована: Июль 3, 2024
Язык: Английский
Purple‐Light Promoted Thiol‐ene Reaction of Alkenes
Advanced Synthesis & Catalysis,
Год журнала:
2023,
Номер
365(24), С. 4623 - 4633
Опубликована: Ноя. 2, 2023
Abstract
Here
we
present
a
catalyst‐free
protocol
for
the
purple
light‐mediated
anti
‐Markovnikov
functionalization
of
alkenes
with
thiols.
Crucial
to
generation
thiyl
radical
was
formation
key
photo‐active
complex.
More
than
30
thioether
products
were
obtained,
demonstrating
tolerance
towards
different
functional
groups
and
scalability
up
5
mmol
alkene.
Two
reaction
conditions
have
been
developed,
varying
both
solvent
amount
thiol.
Depending
on
alkene
structure,
water
can
be
used
as
an
alternative
dichloromethane
solvent,
thus
increasing
sustainability
whole
process.
Язык: Английский
Light-Initiated Four-Step Domino-Multicomponent Synthesis of Functionalized Alkylidenecyclobutanes
Organic Letters,
Год журнала:
2024,
Номер
26(46), С. 9915 - 9919
Опубликована: Ноя. 12, 2024
A
four-step
domino-multicomponent
reaction
(domino-MCR)
is
described
for
the
synthesis
of
functionalized
E-alkylidenecyclobutanes
from
4-hydroxy-2-methylcyclopent-2-enone
derivatives
and
three
other
simple
reagents.
The
domino-MCR
accomplished
in
a
single
protocol,
comprising
tandem
photochemical
[2
+
2]-cycloaddition/Norrish-I/γ-H
transfer
followed
by
an
acetal
protection
allylic
substitution
reaction.
In
parallel,
consecutive
process
has
been
established
with
distinct
nonradiative
sequences.
An
intramolecular
version
these
reactions
provides
access
to
complex
fused-bicyclic
alkylidenecyclobutanes.
Язык: Английский