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.
ACS Catalysis,
Год журнала:
2024,
Номер
14(9), С. 6973 - 6980
Опубликована: Апрель 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
Organic Letters,
Год журнала:
2024,
Номер
26(15), С. 3174 - 3178
Опубликована: Апрель 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,
Год журнала:
2024,
Номер
15(25), С. 9582 - 9590
Опубликована: Янв. 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.
Abstract
Sulfur-containing
compounds
are
found
in
myriad
applications.
Sulfones
and
sulfonamides
the
most
common
functional
groups
used
medicinal
agrochemical
endeavours.
Isosteres
of
these
groups,
for
example,
sulfoximines
sulfonimidamides,
emerging
functionalities,
they
increasingly
relevant
patent
literature.
However,
general,
associated
synthetic
routes
still
have
limitations,
including
use
harsh
reaction
conditions
highly
reactive
reagents.
A
variety
catalytic
reactions
that
employ
a
diverse
range
substrate
classes
been
developed
to
address
issues.
This
short
review
highlights
recent
syntheses
aza-sulfur
compounds,
which
we
hope
will
open
new
directions
discovery
chemistry.
1
Introduction
2
Reactions
N-Sulfinylamines
3
with
Sulfenamides
4
Sulfinates
5
Sulfinamides
6
Other
Aza-Sulfur
Compounds
7
Conclusion
Chemical Science,
Год журнала:
2023,
Номер
15(2), С. 644 - 650
Опубликована: Дек. 5, 2023
A
method
for
the
one
pot
conversion
of
acids
to
free
thiols
is
described.
The
reaction
based
on
ability
a
novel
sulfur
reagent
maintain
regeneration
acridine
photocatalyst.
Development
of
photocatalytic
systems
that
facilitate
mechanistically
different
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
HAT
silane–triplet
system.
study
points
significant
potential
providing
new
directions
