The Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
unknown
Published: Dec. 26, 2024
A
photoredox-catalyzed
aminolactonization
of
unsaturated
carboxylic
acids
was
achieved
using
N-aminopyridinium
salts
as
the
amino
radical
precursor.
The
transformation
features
mild
conditions
and
a
remarkably
broad
substrate
scope,
offering
an
efficient
approach
to
construct
wide
range
4-sulfonamino
3,4-dihydroisocoumarins.
Mechanistic
studies
indicate
that
reaction
proceeds
via
distinctive
salt-promoted
electrophilic
amination
2-styrylbenzoic
acids.
Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(15), P. 2939 - 2944
Published: April 11, 2024
A
selective
three-component
1,2-sulfonyl
etherification
of
aryl
1,3-dienes
enabled
by
copper
catalysis
to
afford
biologically
interesting
alkenyl
1,2-sulfone
ether
derivatives
through
C–S
and
C–O
bond
formation
is
described.
The
protocol
proceeds
with
the
sulfonyl
chloride
alcohols
under
simple,
mild,
base-free
conditions,
providing
a
straightforward
route
sulfonylated
allyl
compounds
broad
functional
group
tolerance
excellent
chemo-
regioselectivity.
Mechanistic
studies
indicate
that
alkene
difunctionalization
includes
key
copper-mediated
single-electron
transfer
process.
Angewandte Chemie International Edition,
Journal Year:
2024,
Volume and Issue:
63(32)
Published: May 24, 2024
Abstract
Radical‐involved
multicomponent
difunctionalization
of
1,3‐dienes
has
recently
emerged
as
a
promising
strategy
for
rapid
synthesis
valuable
allylic
compounds
in
one‐pot
operation.
However,
the
expansion
radical
scope
and
enantiocontrol
remain
two
major
challenges.
Herein,
we
describe
an
unprecedented
photoinduced
copper‐catalyzed
highly
enantioselective
three‐component
1,2‐azidooxygenation
with
readily
available
azidobenziodazolone
reagent
carboxylic
acids.
This
mild
protocol
exhibits
broad
substrate
scope,
high
functional
group
tolerance,
exceptional
control
over
chemo‐,
regio‐
enantioselectivity,
providing
practical
access
to
diverse
azidated
chiral
esters.
Mechanistic
studies
imply
that
copper
complex
is
implicated
bifunctional
catalyst
both
photoredox
catalyzed
azidyl
generation
C−O
cross‐coupling.
Chemical Communications,
Journal Year:
2024,
Volume and Issue:
60(50), P. 6340 - 6361
Published: Jan. 1, 2024
In
this
review,
the
state-of-the-art
advances
in
radical-involved
C(sp
3
)–N
bond
formation
via
metallaphotoredox
catalysis
have
been
highlighted,
which
are
organized
according
to
different
catalytic
modes,
reaction
types,
and
substrate
classes.
Organic Letters,
Journal Year:
2025,
Volume and Issue:
unknown
Published: March 12, 2025
Medium-sized
rings
show
great
potential
in
medicinal
chemistry
but
are
difficult
to
achieve
via
direct
cyclization
reaction.
We
herein
report
a
versatile
and
mild
photocatalytic
approach
for
synthesis
of
medium-
large-sized
vinyl
N-heterocycles
by
radical-mediated
sulfonamides
with
pendant
1,3-dienes.
The
reaction
involves
the
generation
radicals
from
alkyl
halides
π-allylpalladium
species.
This
method
could
serve
as
platform
construction
Pd
catalysis.
We
unveil
a
novel
strategy
that
leverages
cost-effective
fluorine-containing
sources
for
rapid
synthesis
of
fluorinated
com-pounds
through
multicomponent
reactions.
Our
study
introduces
visible
light-driven
palladium-catalyzed
1,4-difluoromethyl
difunctionalization
conjugated
dienes,
capitalizing
on
the
abundant
industrial
resource
chlorodifluoro-methane
(ClCF2H,
Freon-22).
Illuminated
by
blue
LED
light,
palladium
catalyst
orchestrates
efficient
single
electron
reduction
Freon-22's
C-Cl
bond,
yielding
CF2H
radicals.
This
versatile
protocol
accommodates
an
extensive
array
amines,
sulfinates,
and
enolates
as
nucleophiles,
delivering
regioselective
products
via
SN2'
substitution
allylic
intermediate.
Redox-neutral
in
nature,
this
transformation
finds
utility
late-stage
functionalization
drug
molecules,
while
broad
compatibility
with
diverse
functional
groups
dienes
underscores
its
versa-tility.
Initial
insights
suggest
involvement
difluoromethyl
radical
intermediate,
unveiling
direct
mild
avenue
to
harness
radicals
from
Freon-22.
Organic Letters,
Journal Year:
2025,
Volume and Issue:
unknown
Published: Feb. 22, 2025
A
copper-based
catalytic
system
has
been
described
to
enable
the
efficient
1,4-sulfonylindolylation
of
1,3-dienes
with
sulfonyl
chloride
and
indoles.
This
protocol
offers
a
practical
method
for
synthesis
allylsulfone-containing
indole
derivatives
broad
range
compatible
functionalities
excellent
chemo-
regioselectivities.
Mechanistic
studies
suggest
that
copper
catalyst
plays
dual
role
initiating
radicals
prompting
coupling
in
this
conjugated
diene-selective
1,4-difunctionalization
strategy.
Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(7), P. 1387 - 1392
Published: Feb. 11, 2024
We
report
a
copper-catalyzed
selective
1,2-phosphonoazidation
of
conjugated
dienes.
This
three-component
reaction
is
achieved
by
using
readily
available
P(O)–H
compounds
and
bench-stable
NaN3.
Salient
features
this
strategy
include
its
mild
conditions,
broad
functional
group
tolerance,
high
chemoselectivity
regioselectivity.
Moreover,
the
compatibility
with
late-stage
functionalization
drug
molecules,
potential
for
scalable
production,
feasibility
further
modifications
products
underscore
practical
utility
protocol
in
synthetic
applications.
Synthesis,
Journal Year:
2024,
Volume and Issue:
56(16), P. 2558 - 2564
Published: May 23, 2024
Abstract
A
dual
cobalt
and
chromium
photoredox-catalyzed
allylation
of
aldehydes
with
allenes
through
a
photo
metal-hydride
atom
transfer
(MHAT)
process
has
been
developed
to
yield
homoallylic
alcohols
exceptional
diastereoselective
control.
This
sustainable
efficient
method
holds
significant
promise
for
applications
in
the
synthesis
valuable
organic
compounds.
