Organic Letters,
Journal Year:
2024,
Volume and Issue:
unknown
Published: Oct. 1, 2024
More
than
450
drugs
containing
a
carboxylic
acid
functional
group
have
been
marketed
worldwide.
Herein,
we
report
concise
and
environmentally
friendly
organic
photoinduced
protocol
for
the
interconversion
of
acids
into
their
bioisosteres.
With
this
strategy,
variety
substrates,
including
alkyl,
(hetero)aryl,
alkenyl
acids,
as
well
various
biologically
relevant
are
successfully
converted
primary
sulfonamides.
Journal of the American Chemical Society,
Journal Year:
2023,
Volume and Issue:
145(43), P. 23814 - 23823
Published: Oct. 18, 2023
Radical
remote
1,n-difunctionalization
reactions
(n
>
2)
of
alkenes
are
powerful
tools
to
efficiently
introduce
functional
groups
with
selected
distances
into
target
molecules.
Among
these
reactions,
1,5-difunctionalizations
an
important
subclass,
leading
sought-after
scaffolds,
but
typically
suffer
from
tailored
starting
materials
and
strict
limitations
for
the
formed
group
in
2-position.
Seeking
address
issues
make
radical
more
applicable,
we
report
a
novel
three-component
1,2,5-trifunctionalization
reaction
between
imine-based
bifunctional
reagents
two
distinct
alkenes,
driven
by
visible
light
energy
transfer-catalysis.
Key
achieving
this
selective
one-step
installation
three
different
via
choreographed
formation
four
bonds
was
utilization
1,2-boron
shift
rigorous
capitalization
polarities
stabilities.
Thorough
mechanistic
studies
were
carried
out,
synthetic
utility
obtained
products
demonstrated
various
downstream
modifications.
Notably,
addition
functionalization
individual
groups,
their
interplay
gave
rise
unique
array
cyclic
products.
Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(3), P. 713 - 718
Published: Jan. 12, 2024
Sulfonamides
are
important
structures
in
pharmaceuticals,
agrochemicals,
and
organocatalysts,
yet
the
rapid
benign
synthesis
of
these
compounds
is
still
a
great
challenge.
Herein
we
report
photoinduced
method
for
synthesizing
sulfonamides
from
(hetero)aryl
carboxylic
acid
oxime
esters.
This
reaction
proceeds
via
one-pot
cascade
radical–radical
cross-coupling
by
energy-transfer-mediated
photocatalysis.
A
wide
substrate
scope
including
substrates
late-stage
modification
pharmaceutical
molecular
entities
reveal
its
generality.
ACS Catalysis,
Journal Year:
2025,
Volume and Issue:
15(3), P. 1854 - 1941
Published: Jan. 17, 2025
Over
the
past
decade,
visible-light-mediated
energy-transfer
(EnT)
catalysis,
particularly
triplet–triplet
(TTEnT)
has
emerged
as
a
mild
and
environmentally
friendly
approach
for
diverse
organic
synthetic
transformations.
In
contrast
to
photoredox
which
typically
requires
sacrificial
electron
donors
or
acceptors
complete
catalytic
cycle,
EnT
photocatalysis
generally
proceeds
with
high
atom
economy
while
minimizing
generation
of
wasteful
byproducts.
Furthermore,
successful
catalysis
is
contingent
upon
precise
control
redox
potentials
both
photocatalysts
substrates,
strategies
are
primarily
influenced
by
triplet
energy
compatibility
between
these
entities.
Considering
growing
importance
photocatalysis,
well
hydrofunctionalization
difunctionalization
reactions
in
synthesis,
this
review
systematically
summarizes
significant
advancements
EnT-enabled
unsaturated
compounds
via
sigma-bond
homolysis
over
decade.
Special
emphasis
placed
on
elucidating
substrate
scopes
mechanistic
scenarios.
Additionally,
discusses
versatile
applications
methodologies
addresses
current
challenges
opportunities
within
evolving
research
field.
This
structured
into
six
main
categories
based
different
types
sigma-bonds
undergoing
homolysis.
These
include
transformations
mediated
1)
N–O
bond
oxime
esters
other
N,O-radical
precursors;
2)
N–S
N-sulfonyl
imines
N,S-radical
3)
chalcogen–chalcogen
disulfides
oxy/thio/selenosulfonates;
4)
C–S
tri/difluoromethylated
sulfinates,
acetylenic
triflones,
arylsulfonium
salts;
5)
C–X
(X
=
halogen)
halides;
6)
acceptors.
Through
providing
theoretical
backgrounds
along
comprehensive
overview
currently
employed
acceptors,
photosensitizers,
contemporary
EnT-induced
compounds,
aims
serve
an
invaluable
resource
future
innovations
rapidly
Organic Letters,
Journal Year:
2025,
Volume and Issue:
unknown
Published: Feb. 17, 2025
A
metal-free
photosensitized
1,2-imino-thiocyanation
of
olefins
has
been
established
by
using
the
easily
accessible
bifunctional
reagent
S-cyano-N-(diphenylmethylene)
thiohydroxylamine.
wide
range
were
successfully
transformed
into
corresponding
β-iminothiocyanates
in
moderate
to
high
yields.
This
protocol
stands
out
for
its
nature,
broad
substrate
compatibility,
and
atom
step
economy,
providing
an
effective
strategy
assembling
β-amino
thiocyanate-containing
scaffolds.
Green Chemistry,
Journal Year:
2023,
Volume and Issue:
25(10), P. 3857 - 3863
Published: Jan. 1, 2023
A
general
and
environmentally
friendly
organic
photo-induced
strategy
was
developed
for
the
synthesis
of
diverse
alkyl-substituted
β-amino
sulfone
derivatives,
including
primary,
secondary,
tertiary
products.
Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(9), P. 1920 - 1925
Published: Feb. 22, 2024
A
photocatalytic
three-component
sulfonyl
peroxidation
of
alkenes
with
N-sulfonyl
ketimines
and
tert-butyl
hydroperoxide
is
reported.
The
reaction
takes
place
via
the
photoinduced
EnT
process,
which
allows
efficient
synthesis
a
variety
β-peroxyl
sulfones
under
mild
conditions
in
absence
transition
metal
catalyst.
downstream
derivatizations
peroxides
were
also
performed.
Furthermore,
utility
this
protocol
was
manifested
by
11β-HSD1
inhibitor
antiprostate
cancer
drug
bicalutamide.
Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(10), P. 2108 - 2113
Published: March 5, 2024
A
metal-free
photosensitized
1,2-imino-sulfamoylation
of
olefins
by
employing
a
tailor-made
sulfamoyl
carbamate
as
the
difunctionalization
reagent
has
been
established.
This
protocol
exhibits
versatility
across
broad
substrate
scope,
including
aryl
and
aliphatic
alkenes,
leading
to
synthesis
diverse
β-imino
sulfonamides
in
moderate
good
yields.
method
is
characterized
its
reaction
system,
mild
conditions,
excellent
regioselectivity,
high
atom
economy,
serving
promising
platform
for
preparation
β-amino
sulfonamide-containing
molecules,
particularly
context
drug
discovery.
Organic Letters,
Journal Year:
2023,
Volume and Issue:
25(45), P. 8067 - 8071
Published: Nov. 8, 2023
A
visible-light-induced
β-acyl
difunctionalization
of
alkenes
with
acyl
oxime
esters
and
various
nucleophiles
was
developed
to
achieve
molecular
complexity
from
readily
available
raw
materials
via
oxidative
radical-polar
crossover.
variety
nucleophiles,
including
NH-sulfoximines,
indoles,
indazole,
trimethoxybenzene,
were
all
effectively
applicable
the
sustainable
reaction
system.
The
novel
synthetic
strategy
features
mild
conditions,
a
broad
substrate
scope
(39
examples),
easy
scale-up,
excellent
regioselectivity.
Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(30), P. 6396 - 6401
Published: July 24, 2024
Spirocyclobutyl
oxindoles
have
garnered
substantial
attention
in
drug
discovery
and
pharmaceuticals
owing
to
their
wide
range
of
biological
activities.
Strain-release
small-ring
compounds
is
a
powerful
strategy
enable
efficient
access
complex
molecules.
In
this
study,
we
successfully
realized
photoredox-catalyzed
strain-release
radical
spirocyclization
approach
attain
functionalized
spirocyclobutyl
oxindoles.
A
diverse
array
radicals,
such
as
sulfonyl,
phosphonyl,
trifluoromethyl,
were
added
efficiently
the
strained
C-C
σ-bond
bicyclobutanes
(BCBs)
afford
library
Furthermore,
obtained
products
could
be
transformed
into
valuable
building
blocks.
The
observed
reactivity
selectivity
been
rationalized
based
on
density
functional
theory
calculations.
Organic Chemistry Frontiers,
Journal Year:
2025,
Volume and Issue:
unknown
Published: Jan. 1, 2025
We
report
a
visible-light-mediated
three-component
reaction
via
1,5-HAT
combined
with
site-selective
remote
C(sp
3
)–H
cross-coupling
reactions
of
alkenes
alkyl
radicals
for
the
α-C(sp
alkylation
glycine
derivatives
and
peptides.
