The Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
89(14), P. 10223 - 10233
Published: June 28, 2024
A
photo-induced
cascade
sulfone
alkylation/cyclization
of
2-isocyanoaryl
thioethers
is
explored.
This
visible-light-triggered
reaction
not
only
occurs
under
extremely
mild
conditions
but
also
does
require
the
presence
a
photosensitizer.
The
photocatalytic
process
triggered
by
photochemical
activity
in
situ-generated
electron
donor–acceptor
complexes,
arising
from
association
and
α-iodosulfones.
radical
pathway
was
confirmed
UV–vis
spectroscopy,
trapping,
Job's
plot,
on/off
irradiation
experiments.
Chemistry - A European Journal,
Journal Year:
2024,
Volume and Issue:
30(31)
Published: March 28, 2024
Abstract
Photoinduced
aryl
radical
generation
is
a
powerful
strategy
in
organic
synthesis
that
facilitates
the
formation
of
diverse
carbon‐carbon
and
carbon‐heteroatom
bonds.
The
synthetic
applications
photoinduced
complex
compounds,
including
natural
products,
physiologically
significant
molecules,
functional
materials,
have
received
immense
attention.
An
overview
current
developments
production
methods
their
uses
given
this
article.
A
generalized
idea
how
to
choose
reagents
approach
for
radicals
described,
along
with
techniques
associated
mechanistic
insights.
Overall,
article
offers
critical
assessment
results
as
well
selection
reaction
parameters
specific
context
cascades,
cross‐coupling
reactions,
functionalization,
selective
C−H
functionalization
substrates.
Journal of the American Chemical Society,
Journal Year:
2024,
Volume and Issue:
146(23), P. 15850 - 15859
Published: May 28, 2024
Light-driven
strategies
that
enable
the
chemoselective
activation
of
a
specific
bond
in
multifunctional
systems
are
comparatively
underexplored
comparison
to
transition-metal-based
technologies,
yet
desirable
when
considering
controlled
exploration
chemical
space.
With
current
drive
discover
next-generation
therapeutics,
reaction
design
enables
strategic
incorporation
an
sp3
carbon
center,
containing
multiple
synthetic
handles
for
subsequent
space
would
be
highly
enabling.
Here,
we
describe
photoactivation
ambiphilic
C1
units
generate
α-bimetalloid
radicals
using
only
Lewis
base
and
light
source
directly
activate
C–I
bond.
Interception
these
transient
with
various
SOMOphiles
rapid
synthesis
organic
scaffolds
(B,
Si,
Ge)
orthogonal
activation.
In-depth
theoretical
mechanistic
studies
reveal
prominent
role
2,6-lutidine
forming
photoactive
charge
transfer
complex
stabilizing
situ
generated
iodine
radicals,
as
well
influential
boron
p-orbital
activation/weakening
This
simple
efficient
methodology
enabled
expedient
access
functionalized
3D
frameworks
can
further
derivatized
available
technologies
C–B
C–Si
Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(3), P. 636 - 641
Published: Jan. 10, 2024
A
photochemical
halogen-bonding-assisted
synthesis
of
vinyl
sulfones
via
radical–radical
cross-coupling
bromines
and
sodium
sulfinates
is
developed.
This
methodology
offers
a
facile
efficient
approach
to
various
with
excellent
functional
group
tolerance
under
metal-,
photocatalyst-,
base-,
oxidant-free
conditions.
The
reaction
also
applicable
for
the
late-stage
functionalization
drug
molecules
hectogram
scale.
Moreover,
instead
sulfites
being
prepared,
these
reactions
could
be
conducted
using
sulfonyl
chlorides
in
one-pot
method.
Chemistry - A European Journal,
Journal Year:
2024,
Volume and Issue:
unknown
Published: Feb. 7, 2024
Abstract
Light‐mediated
processes
have
received
significant
attention,
since
they
re‐surfaced
unconventional
reactivity
platforms,
complementary
to
conventional
polar
chemistry.
γ‐Lactones
and
cyclopropanes
are
prevalent
moieties,
found
in
numerous
natural
products
pharmaceuticals.
Among
various
methods
for
their
synthesis,
light‐mediated
protocols
coming
the
spotlight,
although
these
contingent
upon
use
of
photoorgano‐
or
metal‐based
catalysts.
Herein,
we
introduce
a
novel
photochemical
activation
iodo‐reagents
via
cheap
sodium
ascorbate
ascorbic
acid
enable
homolytic
scission
addition
onto
double
bonds.
The
developed
protocol
was
applied
successfully
formal
[3+2]
cycloaddition
synthesis
γ‐lactones,
traditional
atom
transfer
radical
(ATRA)
reactions
one‐pot
two‐step
conversion
alkenes
cyclopropanes.
In
all
cases,
desired
were
obtained
good
high
yields,
while
reaction
mechanism
thoroughly
investigated.
Depending
on
nature
iodo‐reagent,
halogen
hydrogen‐bonded
complex
is
formed,
which
initiates
process.
Chemical Society Reviews,
Journal Year:
2024,
Volume and Issue:
53(10), P. 4926 - 4975
Published: Jan. 1, 2024
In
search
for
the
perfect
wave(length).
This
review
is
dedicated
to
recent
efforts
in
development
of
visible
light
driven
photochemical
strategies
occurring
coloured
organic
compounds.
Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(12), P. 2440 - 2444
Published: March 19, 2024
An
iodoarene-driven
electroreductive
remote
C(sp3)–H
arylation
of
unsymmetrical
1-(o-iodoaryl)alkyl
ethers
with
cyanoarenes
for
the
site
selective
synthesis
α-(hetero)aryl
is
developed.
With
introduction
as
both
aryl
sources
and
electron
transfer
mediators,
this
method
includes
an
strategy
to
enable
regiocontrollable
formation
two
new
bonds,
one
C(sp2)–H
bond,
C(sp2)–C(sp3)
in
a
single
reaction
step
through
sequence
halogen
atom
(XAT),
hydrogen
(HAT),
radical–radical
coupling,
decyanation.
Advanced Synthesis & Catalysis,
Journal Year:
2024,
Volume and Issue:
366(6), P. 1422 - 1429
Published: Feb. 1, 2024
Abstract
The
photochemical
catalyst‐free
radical‐based
synthesis
of
vinyl
and
1,3‐dienyl
sulfones
is
disclosed.
Mechanistic
investigations
support
that
the
transformations
rely
on
a
visible‐light‐promoted
activation
halogen‐bonding
complex,
which
formed
between
an
alkenyl
(or
1,3‐dienyl)
bromide
sodium
sulfinate
salt.
reactions
exhibit
wide
functional
group
tolerance
(compatible
with
heteroatoms,
electron‐withdrawing
electron‐donating
groups),
finding
application
in
structural
modification
biologically
relevant
molecules.
Eventually,
continuous
flow
protocol
was
developed
to
upscale
these
transformations.
Advanced Science,
Journal Year:
2024,
Volume and Issue:
unknown
Published: Dec. 31, 2024
Abstract
Introducing
distinctive
functional
groups
to
expand
the
structural
diversity
and
improve
intrinsic
properties
of
parent
molecules
has
been
an
essential
pursuit
in
organic
chemistry.
By
using
perfluoroalkyl
halide
(PFAH)
as
a
nontraditional,
readily
available,
ideal
1,2‐difluoroalkenyl
coupling
partner,
defluorinative
cyclization
reaction
enamides
for
construction
fluoroalkenyl
oxazoles
is
first
developed.
The
selective
controllable
two‐fold
cleavage
vicinal
C(sp
3
)─F
bonds
PFAH
not
only
enables
introduction
specific
moiety
with
ease
but
also
results
functionalization
two
2
)─H
without
need
metal
catalyst,
photocatalyst,
oxidant,
or
light.
method
can
be
applied
late‐stage
modification
complex
molecules,
synthesis
biological‐relevant
oxazole
analoges,
scale‐up
synthesis,
which
all
further
highlight
real‐world
utility
this
protocol.
Mechanistic
studies
reveal
that
possibly
proceeds
through
radical
perfluoroalkylation,
consecutive
C─F
bond
heterolytic
cleavage,
process.
In
addition,
situ
formed
may
serve
hydrogen
abstractor.
