The
thiol
group
is
one
of
the
most
biologically
important
and
synthetically
versatile
organosulfur
functionalities
that
can
serve
as
a
central
entry
point
to
wide
range
other
sulfur-containing
functional
groups.
Despite
their
cross-disciplinary
importance,
synthetic
access
thiols
largely
remains
dominated
by
two-electron-mediated
processes
based
on
toxic
uneconomical
reagents
precursors.
We
report
herein
photocatalytic
for
first
time
merges
structural
diversity
carboxylic
acids
with
ready
availability
elemental
sulfur,
whose
radical
reactivity
significantly
underexplored.
two-phase
process
facilitated
multimodal
catalytic
acridine
photocatalysis
enables
both
PCET-mediated
decarboxylative
carbon–sulfur
bond
formation
previously
unknown
reductive
disulfur
cleavage
photoinduced
HAT
in
silane–acridine
system.
Journal of the American Chemical Society,
Journal Year:
2024,
Volume and Issue:
146(12), P. 8508 - 8519
Published: Feb. 21, 2024
Tricomponent
cobalt(salen)-catalyzed
carbofunctionalization
of
unsaturated
substrates
by
radical-polar
crossover
has
the
potential
to
streamline
access
broad
classes
heteroatom-functionalized
synthetic
targets,
yet
reaction
platform
remained
elusive,
despite
well-developed
analogous
hydrofunctionalizations
mediated
high-valent
alkylcobalt
intermediates.
We
report
herein
development
a
cobalt(salen)
catalytic
system
that
enables
carbofunctionalization.
The
entails
tricomponent
decarboxylative
1,4-carboamination
dienes
and
provides
direct
route
aromatic
allylic
amines
obviating
preformed
allylation
reagents
protection
oxidation-sensitive
amines.
merges
acridine
photocatalysis
with
regioselective
1,4-carbofunctionalization
facilitates
radical
polar
phases
coupling
process,
revealing
critical
roles
reactants,
as
well
ligand
effects
nature
formal
species
on
chemo-
regioselectivity.
ACS Catalysis,
Journal Year:
2024,
Volume and Issue:
14(9), P. 6973 - 6980
Published: April 19, 2024
Development
of
photocatalytic
systems
that
facilitate
mechanistically
divergent
steps
in
complex
catalytic
manifolds
by
distinct
activation
modes
can
enable
previously
inaccessible
synthetic
transformations.
However,
multimodal
remain
understudied,
impeding
their
implementation
methodology.
We
report
herein
a
access
to
thiols
directly
merges
the
structural
diversity
carboxylic
acids
with
ready
availability
elemental
sulfur
without
substrate
preactivation.
The
transformation
provides
direct
radical-mediated
segue
one
most
biologically
important
and
synthetically
versatile
organosulfur
functionalities,
whose
accessibility
remains
largely
dominated
two-electron-mediated
processes
based
on
toxic
uneconomical
reagents
precursors.
two-phase
radical
process
is
facilitated
reactivity
acridine
photocatalysis
enables
both
singlet
excited
state
PCET-mediated
decarboxylative
carbon–sulfur
bond
formation
unknown
reductive
disulfur
cleavage
photoinduced
hydrogen
atom
transfer
silane–triplet
system.
study
points
significant
potential
providing
unexplored
directions
Journal of the American Chemical Society,
Journal Year:
2025,
Volume and Issue:
147(6), P. 4736 - 4742
Published: Jan. 31, 2025
The
preparation
of
alcohols
with
anti-Markovnikov
selectivity
directly
from
olefins
and
water
is
a
sought-after
reaction
due
to
its
atom-economy
potential
cost-effectiveness.
Herein,
we
present
the
first
general
method
for
direct,
catalytic
hydration
unconjugated
tri-
disubstituted
olefins.
key
advancement
made
possible
by
an
oxidative
(E*red
=
2.15
V)
N-H
acridinium
catalyst,
which
allowed
functionalization
alkenes
that
were
previously
unreactive
in
such
transformations
their
high
oxidation
potential.
developed
protocol
not
limited
but
also
enables
other
hydrofunctionalizations,
as
hydroetherifications,
following
same
mechanistic
pathway.
Chemical Science,
Journal Year:
2023,
Volume and Issue:
14(46), P. 13384 - 13391
Published: Jan. 1, 2023
Sulfinamides
are
some
of
the
most
centrally
important
four-valent
sulfur
compounds
that
serve
as
critical
entry
points
to
an
array
emergent
medicinal
functional
groups,
molecular
tools
for
bioconjugation,
and
synthetic
intermediates
including
sulfoximines,
sulfonimidamides,
sulfonimidoyl
halides,
well
a
wide
range
other
S(iv)
S(vi)
functionalities.
Yet,
accessible
chemical
space
sulfinamides
remains
limited,
approaches
largely
confined
two-electron
nucleophilic
substitution
reactions.
We
report
herein
direct
radical-mediated
decarboxylative
sulfinamidation
first
time
enables
access
from
broad
structurally
diverse
carboxylic
acids.
Our
studies
show
formation
prevails
despite
inherent
thermodynamic
preference
radical
addition
nitrogen
atom,
while
machine
learning-derived
model
facilitates
prediction
reaction
efficiency
based
on
computationally
generated
descriptors
underlying
reactivity.
Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(15), P. 3174 - 3178
Published: April 8, 2024
A
concept
for
the
dual
use
of
acridine
and
tetrabutylammonium
decatungstate
photocatalysts
in
reactions
carboxylic
acids
is
proposed.
Imines
generated
situ
from
aldehydes
p-methoxyaniline,
as
well
other
azomethines,
were
used
radical
acceptors.
The
role
believed
to
facilitate
turnover
photocatalyst
by
means
hydrogen
atom
transfer.
Chemical Science,
Journal Year:
2024,
Volume and Issue:
15(25), P. 9582 - 9590
Published: Jan. 1, 2024
Diverse
amines
and
amino
acids
are
now
readily
accessed
from
carboxylic
acids,
aldehydes,
amine
precursors
in
a
direct
decarboxylative
reaction
enabled
by
homogeneous
triple
catalytic
system
based
on
acridine
photocatalysis.
Chemistry - A European Journal,
Journal Year:
2023,
Volume and Issue:
29(67)
Published: Aug. 30, 2023
A
mild,
practical,
and
environmentally
friendly
method
for
the
hydrodecarboxylation
of
fatty
acids
using
an
acridine-based
photoredox
catalyst
thiophenol
was
developed.
Cn-1
alkanes
were
synthesized
in
good
to
excellent
yields
(up
99
%)
from
C10-C18
saturated
under
visible
light
irradiation
(405
nm).
The
developed
protocol
employed
a
mixture
obtained
hydrolysis
Licuri
oil,
affording
C9-C17
hydrocarbons
quantitative
yield,
which
demonstrates
potential
application
produce
drop-in
biofuels.
European Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
unknown
Published: June 26, 2024
Abstract
The
copper‐catalyzed
azide
alkyne
[3+2]‐cycloaddition
(CuAAC)
reaction
of
organoboranes
represents
an
attractive
area
research
within
the
field
click
chemistry,
with
diverse
applications
in
organic
synthesis,
medicinal
or
materials
science.
Despite
potential
issues
caused
by
copper
insertion
into
carbon‐boron
bond,
significant
progress
has
been
made
to
harness
reactivity
organoboron
compounds
CuAAC.
This
review
provides
overview
catalytic
methods
reported
for
CuAAC
various
organoboranes,
discussing
stability
boron
group
and
highlighting
recent
advancements
this
area.
Organic Chemistry Frontiers,
Journal Year:
2025,
Volume and Issue:
unknown
Published: Jan. 1, 2025
Homologation
of
carboxylic
acids
with
a
tosylhydrazone
reagent
is
described.
The
reaction
performed
using
dual
acridine/decatungstate
photocatalytic
system.
