Abstract
The
establishment
of
all‐carbon
quaternary
carbon
centers
represents
a
pivotal
aspect
in
the
synthesis
numerous
natural
products
and
pharmaceutical
compounds,
underscoring
its
paramount
significance
synthetic
organic
chemistry.
Herein,
we
present
novel
strategy
for
generation
through
reductive
coupling
tertiary
halides,
catalyzed
by
dinuclear
(salen)titanium
catalysts.
This
catalytic
framework
demonstrates
notable
reactivity
towards
chlorides
while
maintaining
inertness
secondary
primary
chlorides,
thereby
facilitating
exceptional
chemoselectivity
C−C
bond
formation.
reaction
proceeds
with
remarkable
efficiency
across
diverse
range
substrates
under
mild
conditions.
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(6), С. 4120 - 4127
Опубликована: Март 5, 2024
Heteroatom-adjacent
C(sp3)
radical
cyclization
of
N-arylacrylamides
provides
a
straightforward
pathway
to
synthesize
valuable
3-functionalized
oxindoles.
Traditional
reactions
normally
require
harsh
conditions
or
transition-metal
catalysts.
Here,
we
developed
metal-free,
diversity-oriented
synthesis
oxindoles
via
photochemically
induced
selective
cleavage
C(sp3)–H
bonds.
A
variety
3-substituted
with
functionalities
such
as
ethers,
polyhalogens,
benzyl,
and
formyl
groups
can
be
obtained
by
rational
design.
This
strategy
is
characterized
its
simple
operation
mild
conditions,
aligning
well
the
developmental
requirements
for
sustainable
chemistry.
The
gram-scale
continuous-flow
efficient
construction
bioactive
molecules
highlight
practical
utility.
Journal of the American Chemical Society,
Год журнала:
2024,
Номер
unknown
Опубликована: Сен. 12, 2024
The
ligated
boryl
radical
(LBR)
has
emerged
as
a
potent
tool
for
activating
alkyl
halides
in
transformations
through
halogen-atom
transfer
(XAT).
However,
unactivated
chlorides
still
present
an
open
challenge
this
strategy.
We
herein
describe
new
activation
mode
of
the
LBR
to
construct
C(sp
Organic & Biomolecular Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Янв. 1, 2025
A
visible-light-induced
deoxygenative
alkylation/cyclization
of
acrylamides
with
alcohols
activated
by
CS
2
has
been
developed
using
xanthate
salts
as
alkyl
radical
precursors
in
the
presence
tricyclohexylphosphine.
Organic & Biomolecular Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Янв. 1, 2025
We
present
a
photoredox
nickel-catalyzed
intermolecular
cyclization
between
N
-arylacrylamides
and
readily
accessible
alkyl
bromides,
which
affords
diverse
range
of
3,3-disubstituted
oxindoles
in
moderate
to
high
yields.
The Journal of Organic Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Март 19, 2025
Herein,
we
developed
alkyl
radical
generation
from
C(sp3)–H
bonds
of
alkanes
via
a
photoinduced
HAT-process
without
employing
an
external
metal,
photocatalyst,
and
organic
peroxide.
The
generated
participates
in
addition
cascade
cyclization
N-arylacrylamides/N-acryloyl
benzamides
to
deliver
structurally
diverse
valuable
functionalized
oxindoles
isoquinolinediones
moderate
good
yields.
Preliminary
mechanistic
studies
indicated
the
aryl
through
homolytic
cleavage
Ar–I
direct
photoexcitation
iodide.
In
this
report,
we
present
the
synthesis
of
2-aryl
indoles
via
an
organo-photocatalytic
pathway
at
room
temperature.
The
catalysts
are
commercially
available
phenothiazine
and
phenoxazine,
which
upon
deprotonation
become
very
strong
reductants
cleave
a
C-Cl
bond
to
steer
radical
process
for
targeted
synthesis.
We
proved
that
deprotonated
phenoxazine
extremely
potent
reaching
excited-state
reducing
ability
up
-3.41
V
vs
saturated
calomel
electrode.
Photophysical
studies
revealed
their
great
light-absorbing
properties,
can
facilitate
functionalizing
indole
molecules
under
such
mild
reaction
condition.
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(17), С. 12693 - 12700
Опубликована: Авг. 26, 2024
FeTiO3
has
emerged
as
an
interesting
semiconductor
photocatalyst
in
organic
synthesis.
We
herein
describe
a
visible-light-induced
semiheterogeneous
strategy
for
the
synthesis
of
3-(2-oxoethyl)indolin-2-ones
with
moderate
to
good
yields
and
functional
group
compatibility
using
recyclable
NHPI
redox
catalyst.
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(17), С. 11950 - 11958
Опубликована: Авг. 19, 2024
An
environmentally
friendly
electrochemical
strategy
for
the
synthesis
of
SCF3-containing
oxindoles
was
developed.
This
transformation
accomplished
through
a
cascade
trifluoromethylthiolation/cyclization
N-acrylamides
with
AgSCF3,
obviating
requirement
external
oxidants.
A
variety
functional
groups
were
well
tolerated
in
this
transformation.
European Journal of Organic Chemistry,
Год журнала:
2024,
Номер
27(45)
Опубликована: Авг. 28, 2024
Abstract
A
photocatalyst‐free
cascade
reaction
of
N
‐alkyl‐
‐arylmethacrylamides
with
monoalkyl
cesium
oxalate
salts
is
described.
In
the
presence
visible
light
and
(NH
4
)
2
S
O
8
,
undergo
single‐electron
oxidation/CO
extrusion
to
generate
alkyl
radicals,
followed
by
addition
subsequent
cyclization
give
alkylated
oxindoles.
addition,
‐methacryloylbenzamides
could
be
applied
for
reaction,
providing
a
series
isoquinolinediones,
which
are
completely
different
from
products
obtained
oxalates
as
substrates.
