Asian Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
12(12)
Published: Nov. 16, 2023
Abstract
Sulfonyl‐tethered
N
‐containing
heterocycles
are
valuable
building
blocks
in
synthetic
and
pharmaceutical
chemistry.
Recently,
the
installation
of
fluoroalkanesulfonyl
groups
into
via
difunctionalization
alkenes
still
remains
challenging.
Herein
this
work,
an
imino‐fluoroalkanesulfonylation
γ,δ‐unsaturated
oxime
esters
has
been
achieved
photoredox/Cu
dual
catalysis.
A
variety
fluoroalkanesulfonyl‐tethered
pyrroline
derivatives
have
readily
synthesized
moderate
to
good
yields
under
mild
conditions.
Angewandte Chemie International Edition,
Journal Year:
2024,
Volume and Issue:
unknown
Published: April 10, 2024
The
photoredox
electron
donor-acceptor
(EDA)
complex-mediated
radical
coupling
reaction
has
gained
prominence
in
the
field
of
organic
synthesis,
finding
widespread
application
two-component
reactions.
However,
EDA
complex-promoted
multi-component
reactions
are
not
well
developed
with
only
a
limited
number
examples
have
been
reported.
Herein,
we
report
photoinduced
and
highly
chemoselective
three-component
arylalkylation
[1.1.1]propellane,
which
allows
direct
functionalization
C(sp
This
review
summarizes
recent
progress
in
EDA
complex-promoted
C–S
bond
formation
using
various
sulfur-containing
substrates
under
mild
conditions
via
visible
light
irradiation.
Journal of the American Chemical Society,
Journal Year:
2025,
Volume and Issue:
unknown
Published: March 25, 2025
Dearomative
skeletal
editing
of
benzenoids
represents
a
promising
yet
challenging
strategy
for
the
rapid
construction
high-value
carbon
frameworks
from
readily
accessible
starting
materials.
Büchner
reaction
is
unique
type
expansive
that
transforms
into
functionalized
cycloheptatrienes.
However,
due
to
challenges
in
compatibility
and
selectivity,
achieving
seamless
integration
this
with
dearomative
cycloaddition
within
unified
system
remains
undeveloped.
Here,
we
demonstrated
an
energy-transfer-induced
intermolecular
range
electronically
diverse
alkynes.
This
protocol
employed
N-acylimines
as
diradical
precursors
efficiently
construct
various
structurally
polycyclic
high
chemo-,
regio-,
diastereoselectivities
have
been
previously
inaccessible.
The
related
general
reactivity
selectivity
issues
were
circumvented
through
smooth
merging
photoinduced
cycloaddition.
Experimental
computational
studies
performed
support
mechanism
interpret
origins
observed
diastereoselectivities.
Organic Letters,
Journal Year:
2025,
Volume and Issue:
unknown
Published: April 3, 2025
A
substrate-regulated
divergent
addition
of
N-sulfonyl
ketimines
to
bicyclo[1.1.0]butanes
(BCBs)
was
developed
using
a
photoinduced
energy
transfer
strategy.
The
[2π+2σ]
cycloaddition
BCBs
with
saccharin-derived
cyclic
yields
benzosultam-fused
aza-BCHs
good
and
excellent
diastereoselectivity.
In
contrast,
reactions
chain
produce
1,3-fully
substituted
cyclobutanes
via
energy-transfer-induced
N-S
bond
homolysis.
ease
large-scale
synthesis
derivatizations
products
highlight
their
application
potentials.
Angewandte Chemie,
Journal Year:
2024,
Volume and Issue:
136(39)
Published: April 10, 2024
Abstract
The
photoredox
electron
donor–acceptor
(EDA)
complex‐mediated
radical
coupling
reaction
has
gained
prominence
in
the
field
of
organic
synthesis,
finding
widespread
application
two‐component
reactions.
However,
EDA
complex‐promoted
multi‐component
reactions
are
not
well
developed
with
only
a
limited
number
examples
have
been
reported.
Herein,
we
report
photoinduced
and
highly
chemoselective
three‐component
arylalkylation
[1.1.1]propellane,
which
allows
direct
functionalization
C(sp
3
)−H
bicyclo[1.1.1]pentanes
(BCP)‐aryl
groups
under
mild
conditions.
A
variety
unnatural
α‐amino
acids,
featuring
structurally
diversified
1,3‐disubstituted
BCP
moieties,
were
synthesized
single‐step
process.
Notably,
leveraging
high
tension
release
unstable
transient
aryl
undergoes
rapid
conversion
into
relatively
stable
tertiary
alkyl
radical,
consequently,
competing
side‐reaction
was
entirely
suppressed.
strategic
use
this
approach
would
be
useful
for
design
diverse
It
is
noteworthy
that
late‐stage
incorporation
pharmacophores
peptides
achieved
both
liquid‐phase
solid‐phase
This
advancement
anticipated
to
significant
potential
future
development
peptide
drugs.
Advanced Synthesis & Catalysis,
Journal Year:
2024,
Volume and Issue:
366(14), P. 3138 - 3143
Published: May 11, 2024
Abstract
Visible‐light‐induced
difunctionalization
of
alkenes
is
a
powerful
strategy
for
constructing
complex
molecules.
Herein,
we
disclose
three‐component
1,2‐alkylpyridylation
under
mild
and
photosensitizers‐free
conditions.
UV‐vis
absorption
spectroscopy
studies
NMR
titration
experiments
indicate
that
the
formation
an
EDA
between
4‐alkyl‐DHPs
4‐cyanopyridines.
Primary,
secondary,
tertiary
C(
sp
3
)‐centered
radicals
were
formed
by
homolytic
cleavage
4‐alkyl‐DHPs.
Gram‐scale
synthesis
late‐stage
functionalization
medicinally
relevant
molecules
showed
synthetic
potential
our
methodology.
Angewandte Chemie International Edition,
Journal Year:
2024,
Volume and Issue:
63(38)
Published: July 2, 2024
Excitation
of
photoactive
electron
donor-acceptor
(EDA)
complexes
to
generate
radical
is
a
promising
approach
in
chemistry.
In
this
study,
we
introduce
new
model
H-bonding
EDA
for
the
selective
hydrothiolation
and
hydroxysulfenylation
carbonyl-activated
alkenes
with
diverse
thiols
under
visible
light
conditions.
The
reliability
complex
has
been
confirmed
by
meticulous
experimental
theoretical
calculations.
Mechanistic
investigations
have
revealed
significant
influence
solvent
determining
whether
excitation
leads
charge
transfer
(CT)
or
energy-charge
(E
Organic Letters,
Journal Year:
2024,
Volume and Issue:
unknown
Published: Sept. 30, 2024
The
development
of
efficient
methods
for
synthesizing
β-silyl
amines
has
long
been
a
significant
goal
in
organic
synthesis.
Previous
mainly
relied
on
the
use
prefunctionalized
substrates
or
special
reagents.
Herein,
we
present
visible-light-promoted
synthesis
approach
amines,
utilizing
combination
photoinduced
energy
and
hydrogen
atom
transfer
processes.
Using
flow
chemistry
technology,
variety
valuable
skeletons,
including
α-amino
esters,
can
be
produced
from
readily
available
feedstocks
such
as
hydrosilanes
simple
alkanes.
Moreover,
strategy's
full-process
fluidized
production
capability
highlights
its
potential
industrial-scale
manufacturing.
Mechanistic
studies
revealed
that
oxime
esters
act
radical
precursors
well
Chemical Communications,
Journal Year:
2024,
Volume and Issue:
unknown
Published: Jan. 1, 2024
The
synthesis
of
β-amino
acid
esters
was
achieved
through
the
combination
three-components
radical
coupling,
hydrogen
atom
transfer
and
energy
processes,
utilizing
alkyl
formates
olefins
as
raw
materials
in
a
light-induced
reaction.
