SynOpen,
Год журнала:
2022,
Номер
06(03), С. 198 - 207
Опубликована: Авг. 23, 2022
Abstract
An
efficient
organo-photocatalytic
method
for
the
synthesis
of
tetrasubstituted
pyrroles
bearing
a
ketone,
ester,
alcohol,
or
nitro
group
at
3-position
has
been
developed.
The
reaction
involves
visible-light-mediated
formal
[3+2]
dipolar
cycloaddition
between
2H-azirines
and
α-substituted
nitroalkenes
followed
by
denitration
debromination
sequence.
notable
features
protocol
are
excellent
regioselectivity,
wide
substrate
scope,
high
yields
products.
ACS Catalysis,
Год журнала:
2024,
Номер
14(10), С. 7664 - 7673
Опубликована: Май 2, 2024
Our
study
proposes
an
approach
to
semiheterogeneous
photocatalysis,
focusing
on
recyclability
challenges.
We
developed
a
method
employing
visible
light
with
photoinert
anhydrous
CeCl3,
rendering
it
into
reusable
photocatalyst.
Despite
being
and
insoluble
in
organic
solvents,
CeCl3
formed
transient
charge
transfer
complex
acetonitrile,
denoted
as
-
NXS
(NBS
or
NCS),
due
the
strong
oxophilicity
of
trivalent
cerium
toward
oxygen.
This
facilitated
visible-light
absorption,
leading
photoexcitation
Ce(III)
complexes
conversion
centers
potent
reductants,
donating
electrons
NXS.
As
proof
concept,
we
demonstrated
reactions
where
NXS,
upon
accepting
electrons,
generated
halide
radicals,
allowing
synthesis
gem-dihaloketones
under
sunlight
from
terminal
aromatic
alkynes
via
C–X
cross-coupling
reactions.
Significantly,
exhibited
without
notable
decomposition,
by
its
regeneration
isolation
through
simple
filtration
postreaction,
underscoring
potential
for
prolonged
use.
Green Chemistry,
Год журнала:
2022,
Номер
24(18), С. 7122 - 7130
Опубликована: Янв. 1, 2022
Syntheses
of
β-keto
sulfones
have
been
reported
using
g-C
3
N
4
as
a
recyclable
photocatalyst
along
with
green
chemistry
metrics
and
eco-scale
evaluation.
Chemistry - An Asian Journal,
Год журнала:
2022,
Номер
17(21)
Опубликована: Сен. 1, 2022
In
the
arena
of
functional
group-oriented
organic
synthesis,
nitrile
or
cyano
functionality
is
immense
importance.
The
presence
nucleophilic
N-atom,
π-coordinating
ability
triple
bond,
and
electrophilic
C-center
imparts
unique
interesting
reactivities.
Owing
to
transform
into
various
other
groups
intermediates,
chemistry
very
rich
diverse.
particular,
involvement
in
numerous
reactions
such
as
inter-
intramolecular
alkyne
insertion,
[2+2+2]
cycloaddition
with
alkynes,
[3+2]
azides,
[4+2]
dienes
allow
synthesis
many
important
carbo-
heterocycles.
Furthermore,
serves
a
directing
group
C-H
bond
functionalization
introduce
diverse
functionalities
participate
radical
acceptor
cascade
strategies
obtain
large
variety
molecules.
This
review
mainly
focuses
on
reactivity
synthetic
application
including
functionalization,
cycloaddition,
thermal
photochemical
strategy.
objective
current
aims
at
bringing
out
striking
collection
nitrile-triggered
transformations.
Advanced Synthesis & Catalysis,
Год журнала:
2023,
Номер
365(20), С. 3413 - 3431
Опубликована: Сен. 12, 2023
Abstract
Due
their
multifaced
applications,
the
access
to
organosulfur
derivatives
in
an
efficient
and
economical
way
is
a
challenge
organic
synthesis.
In
this
context
photochemistry
photocatalysis
play
crucial
role
development
of
innovative
(and
selective)
Carbon‐Sulphur
bond
formation
processes.
The
present
review
aims
collect
most
recent
strategies
achieve
target
under
visible
light
driven
conditions.
Organic Letters,
Год журнала:
2023,
Номер
25(22), С. 4075 - 4079
Опубликована: Май 26, 2023
Herein
we
have
developed
a
strategy
for
chemodivergent
functionalization
of
N-methylalkanamides
via
C-Br
bond
activation
CBr4,
using
an
orthorhombic
CsPbBr3
perovskite
photocatalyst
under
blue
LEDs
(450-470
nm).
The
selectivity
whether
5-exo-trig
spiro
cyclization
or
6-endo-trig
occurred
depended
on
the
stability
radical
intermediate
that
was
formed
after
addition
bromide
to
starting
compound
obtain
3,8-dibromo-1-methyl-4-phenyl-1-azaspiro[4.5]deca-3,6,9-trien-2-on
3-bromo-1-methyl-4-phenyl-1-azaspiro[4.5]deca-3,6,9-triene-2,8-dione
3-bromo-6-(tert-butyl)-1-methyl-4-phenylquinolin-2(1H)-one.
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(3), С. 1784 - 1796
Опубликована: Янв. 12, 2024
The
atom
transfer
radical
addition
(ATRA)
reaction
is
defined
as
a
method
for
introducing
halogenated
compounds
into
alkenes
via
mechanism.
In
this
study,
we
present
an
ATRA
approach
achieving
regioselective
functionalization
of
quinoxalin-2(1H)-ones
by
activating
C–Br
bonds
CBr4
and
subsequent
trihaloalkyl-carbofunctionalization
styrenes
employing
the
9-mesityl-10-methylacridinium
perchlorate
(Fukuzumi)
photocatalyst
under
3W
blue
LED
(450–470
nm)
irradiation.
This
three-component
cascade
process
demonstrates
remarkable
efficiency
in
synthesis
1-methyl-3-(3,3,3-tribromo-1-(4-chlorophenyl)propyl)quinoxalin-2(1H)-one
derivatives.
Advanced Synthesis & Catalysis,
Год журнала:
2023,
Номер
366(2), С. 168 - 182
Опубликована: Дек. 16, 2023
Abstract
Photoinduced
chemical
transformations
have
become
a
promising
aspect
of
organic
synthesis.
This
review
focuses
on
the
recent
advancements
in
harnessing
photoinduced
processes
for
formation
carbon‐chalcogen
(C−O,
C−S,
C−Se,
and
C−Te)
bonds
under
catalyst‐free
conditions.
These
pathways
typically
involve
either
radical
mechanism
or
creation
electron‐donor‐acceptor
(EDA)
complexes.
The
explores
intricacies
underlying
mechanisms,
discusses
limitations,
evaluates
applicability
various
methodologies
this
field.
Notably,
photocatalyst
transition
metal‐free
photochemical
reactions
offer
effective
alternatives
to
enhance
sustainability
research
area.
Asian Journal of Organic Chemistry,
Год журнала:
2023,
Номер
12(8)
Опубликована: Июнь 26, 2023
Abstract
The
upsurge
in
interest
the
development
of
methodologies
for
synthesis
sulfur‐containing
compounds
via
use
visible‐light
has
been
established
as
a
sustainable
tool
organic
chemistry.
Particularly,
mediated
C−S
bond
formation
gained
popularity
due
to
its
operational
simplicity,
minimized
by‐products,
easy
handling,
mild
reaction
conditions,
etc.
Photochemistry
not
only
provides
way
synthesize
complex
molecules
but
also
ability
overcome
many
challenges
which
are
difficult
attain
by
conventional
thermal
pathways.
Owing
biological
importance
compounds,
present
review
focused
on
under
metal‐free
conditions
visible‐light.
objective
current
is
bring
out
unearthing
collection
regarding
photoredox
catalysis.
For
better
understanding,
categorized
according
mode
reactions
viz
,
difunctionalization
alkenes
and
alkynes,
C−H
functionalization,
radical
cyclization.
All
each
sections
described
with
selected
examples
proper
explanation
proposed
mechanism.
The Journal of Organic Chemistry,
Год журнала:
2023,
Номер
88(14), С. 10096 - 10110
Опубликована: Июль 3, 2023
Herein
we
report
a
cascaded
chalcogenation
of
aryl
alkynoates
or
N-arylpropynamides
using
9-mesityl-10-methylacridinium
perchlorate
as
visible
light
photocatalyst
to
obtain
selectively
either
3-sulfenylated/selenylated
coumarins
spiro[4,5]trienones.
In
radical
initiated
process,
the
spiro-cyclization
reaction
was
favored
due
presence
-OMe
-F
substituent
at
para
position
group,
which
helped
stabilize
allylic
intermediate
formed
during
reaction.
Otherwise,
6-endo-trig
cyclization
led
coumarins.
Overall,
new
C–S/C–Se,
C–C,
and
C═O
bonds
were
in
single
step.
The
Stern–Volmer
quenching
study,
EPR
experiments,
ON-OFF
trapping
etc.,
understand
radical-based
mechanism.
