Abstract
A
novel
transition‐metal‐free
regioselective
allylic
C−H
thiolation
of
alkenes
has
been
achieved
by
cross‐dehydrogenative
coupling
strategy.
The
present
protocol
realizes
efficient
and
highly
regio‐
stereo‐selective
functionalization
bonds
under
metal‐free
conditions,
leading
to
a
series
thioethers
in
good
excellent
yields.
Moreover,
this
work
features
mild
reaction
high
step‐
atom‐economy
functional
group
tolerance.
The Journal of Organic Chemistry,
Год журнала:
2023,
Номер
88(2), С. 1049 - 1060
Опубликована: Янв. 4, 2023
A
straightforward
and
efficient
electrochemical
method
for
regioselective
C(sp2)-H
selenylation
sulfenylation
of
substituted
2-amino-1,4-naphthoquinones
has
been
unearthed.
This
oxidative
cross-coupling
reaction
avoids
using
transition
metal
catalysts,
oxidants,
high
temperatures.
The
other
notable
advantages
this
protocol
are
the
tolerance
diverse
functional
groups,
mild
conditions
at
ambient
temperature,
energy
efficiency,
good
to
excellent
yields,
short
times
(in
minutes),
gram-scale
applicability,
eco-friendliness.
The Journal of Organic Chemistry,
Год журнала:
2023,
Номер
88(7), С. 4187 - 4198
Опубликована: Март 14, 2023
A
visible-light-induced
cross-dehydrogenative
methodology
has
been
developed
for
the
regioselective
sulfenylation
of
pyrazolo[1,5-a]pyrimidine
derivatives.
Rose
bengal,
blue
LEDs,
KI,
K2S2O8,
and
DMSO
are
all
essential
this
photocatalytic
transformation.
The
protocol
is
applicable
synthesis
a
library
3-(aryl/heteroaryl
thio)pyrazolo[1,5-a]pyrimidine
derivatives
with
broad
functionalities.
selectivity
scalability
have
also
demonstrated.
Moreover,
efficiency
strategy
pyrazoles,
indole,
imidazoheterocycles,
4-hydroxy
coumarin
proven.
mechanistic
investigation
revealed
radical-based
mechanism
formation
diaryl
disulfide
as
key
intermediate
coupling
reaction.
European Journal of Organic Chemistry,
Год журнала:
2024,
Номер
27(8)
Опубликована: Янв. 19, 2024
Abstract
Over
the
past
few
years,
organic
chemistry
has
used
dye
rose
bengal‘s
ability
to
absorb
visible
light.
In
present‐day
research,
innovation
of
environmentally
friendly
processes
for
carbon‐carbon/carbon‐heteroatoms
(Nitrogen,
Oxygen,
Sulphur,
and
Phosphorus)
bond
formation
great
importance.
The
photocatalyzed
cross‐dehydrogenative
coupling
(CDC)
reactions
using
bengal
(RB)
is
a
promising
technique
creating
carbon‐carbon/carbon‐heteroatom
bonds
directly
from
readily
available
compounds.
Our
review
focuses
on
current
advancement
in
that
uses
bond‐making
synthesize
various
important
molecules
via
CDC
reactions.
Organic & Biomolecular Chemistry,
Год журнала:
2023,
Номер
21(7), С. 1518 - 1530
Опубликована: Янв. 1, 2023
A
highly
efficient
pot,
atom,
and
step
economical
method
for
the
construction
of
pharmacologically
potent
structurally
functionalized
1,4-dihydropyridines,
quaternary
centered
C-3
spiro[indoline-3,4'-pyridines],
C-11
spiro[indeno[1,2-b]quinoxaline-11,4'-pyridines]
via
rose
bengal
photoredox
catalysis
under
blue
LED
irradiation
in
an
aqueous
medium
at
room
temperature
has
been
developed.
The
products
were
isolated
excellent
yields
within
a
short
reaction
time
variety
functional
groups
transition
metal-
ligand-free
energy-efficient
conditions
green
solvent
system
with
high
mass
efficiency
process
intensity,
which
are
key
advantages
current
work.
Advanced Synthesis & Catalysis,
Год журнала:
2023,
Номер
365(11), С. 1714 - 1755
Опубликована: Апрель 12, 2023
Abstract
In
the
last
decade,
free
radicals
have
found
a
wide
application
in
functionalization
of
unsaturated
compounds,
such
as
alkenes,
alkynes,
and
arenes,
via
free‐radical
addition
to
carbon‐carbon
π‐bonds.
these
processes,
intermolecular
attack
on
aromatic
substrates
represents
challenge
due
relatively
high
resistance
π‐system
reactions
comparison
alkene
C=C
bonds.
The
heterocycles
is
especially
interesting
diversity
their
structures
chemical
properties
well
importance
for
medicinal
chemistry,
agrochemistry,
materials
science.
Addition
C‐centered
widely
known
Minisci‐type
well‐reviewed.
this
paper,
we
summarized
main
achievements
less
explored
group
processes:
by
heteroatom‐centered
(O‐,
N‐,
S‐/Se‐,
P‐radicals)
with
emphasis
papers
published
after
2010.
Literature
analysis
revealed
strong
trend
towards
usage
electrochemistry
photoredox‐catalysis
generation
recent
years.
remaining
fundamental
problem
field
lack
experimental
support
proposed
mechanisms
frequent
existence
several
plausible
reaction
pathways.
progress
mechanistic
studies
can
significantly
improve
prediction
optimal
conditions
depending
structure.
Green Chemistry,
Год журнала:
2022,
Номер
24(7), С. 2825 - 2838
Опубликована: Янв. 1, 2022
Electrochemical
and
mechanochemical
synthesis
of
a
new
series
functionalized
dihydrofuro[3,2-
c
]chromenones,
involving
intramolecular
direct
C
sp3
–H
cross
-dehydrogenative
oxygenation
within
the
warfarin
framework,
has
been
accomplished.
The Journal of Organic Chemistry,
Год журнала:
2022,
Номер
87(7), С. 4777 - 4787
Опубликована: Март 18, 2022
A
photochemical
method
for
the
synthesis
of
functionalized
dihydrofuro[3,2-c]chromenones
via
intramolecular
Csp3-H
cross-dehydrogenative
oxygenation
within
a
warfarin
framework
has
been
unearthed.
Advantages
this
protocol
include
abundant
sunlight
or
low-energy
visible
light
as
energy
source,
mild
reaction
conditions,
and
avoidance
metal
catalysts.
New Journal of Chemistry,
Год журнала:
2022,
Номер
46(28), С. 13483 - 13497
Опубликована: Янв. 1, 2022
The
essence
of
photo-
and
electrochemistry:
sulfenylation
selenylation
substituted
benzo[
a
]phenazin-5-ols
through
cross-dehydrogenative
C(sp
2
)–H
functionalization.
Asian Journal of Organic Chemistry,
Год журнала:
2022,
Номер
11(3)
Опубликована: Янв. 21, 2022
Abstract
A
new
synthetic
strategy
for
accessing
a
diverse
series
of
2‐hydroxyphenylated
α‐ketoamides
has
been
achieved
based
on
visible
light
(white
LED/direct
sunlight)‐driven
photocatalytic
decarboxylative
amidation
4‐hydroxycoumarins.
Advantages
this
protocol
include
mild
and
energy‐efficient
reaction
conditions,
the
use
dioxygen
as
reactant,
avoidance
metal
catalysts.
In
addition,
method
offers
pathway
to
install
biologically
potent
hydroxy
group
at
C‐2
position
phenyl
ring
α‐ketoamide
skeleton.
Green Synthesis and Catalysis,
Год журнала:
2022,
Номер
4(3), С. 226 - 230
Опубликована: Апрель 12, 2022
Using
visible
light
as
energy
to
form
free
radicals
has
important
synthetic
value.
A
novel
and
efficient
visible-light-mediated
strategy
been
developed
for
the
generation
of
thiobenzene
through
cerium-catalyzed
activation
disulfides.
Through
this
photochemical
reaction,
various
3-sulfenylated
quinoxalin-2(1H)-ones
can
be
conveniently
obtained
in
good
yields
with
functional
group
tolerance.
Our
transformation
provides
an
alternative
that
allows
rapid
access
C3
sulfenylated
a
sustainable
practical
manner.
