The Journal of Organic Chemistry,
Journal Year:
2025,
Volume and Issue:
unknown
Published: Feb. 21, 2025
We
presented
a
highly
efficient
palladium-catalyzed
site-selective
C-H
sulfonylation
reaction
via
aryl
thianthrenium
salts.
By
utilizing
readily
available
and
cost-effective
arenes
along
with
sodium
sulfinates,
we
achieved
the
C(sp2)-S
cross-coupling
high
efficiency,
establishing
dependable
method
for
synthesizing
diarylsulfones
satisfactory
yields.
This
exhibits
excellent
tolerance
toward
functional
groups,
scalability,
synthesis
or
late-stage
functionalization
of
bioactive
molecules,
making
it
valuable
tool
drug
modifications.
Chemical Science,
Journal Year:
2022,
Volume and Issue:
13(46), P. 13690 - 13707
Published: Jan. 1, 2022
This
review
summarizes
the
synthesis
of
diverse
organothianthrenium
salts
from
various
precursors
and
their
applications
in
organic
to
forge
new
C–C,
C–H
C–heteroatom
bonds
by
C–S
bond
cleavage
with
different
mechanistic
considerations.
Journal of the American Chemical Society,
Journal Year:
2023,
Volume and Issue:
145(18), P. 10431 - 10440
Published: April 26, 2023
Great
success
in
synthetic
chemistry
is
motivated
by
the
development
of
novel
and
reactive
linchpins
for
carbon-carbon
carbon-heteroatom
bond
formation
reactions,
which
has
dramatically
altered
chemists'
approach
to
building
molecules.
Herein,
we
report
ready
synthesis
aryl
sulfonium
salts,
a
versatile
electrophilic
linchpin,
via
Cu-mediated
thianthrenation
phenoxathiination
commercially
available
arylborons
with
thianthrene
phenoxathiine,
providing
series
salts
high
efficiency.
More
importantly,
leveraging
sequential
Ir-catalyzed
C-H
borylation
arylborons,
formal
arenes
also
achieved.
The
undirected
normally
occurred
at
less
steric
hindrance
position,
thus
complementary
method
comparison
thianthrenation.
This
process
capable
late-stage
functionalization
pharmaceuticals,
might
find
wide
applications
both
industry
academic
sectors.
Organic Letters,
Journal Year:
2023,
Volume and Issue:
25(4), P. 581 - 586
Published: Jan. 25, 2023
A
practical
electrochemically
driven
method
for
fluorosulfonylation
of
both
aryl
and
alkyl
thianthrenium
salts
has
been
disclosed.
The
strategy
does
not
need
external
redox
reagents
or
metal
catalysts.
In
combination
with
C-H
thianthrenation
aromatics,
this
provides
a
new
tool
the
site-selective
drugs.
Nature Communications,
Journal Year:
2024,
Volume and Issue:
15(1)
Published: Jan. 15, 2024
Abstract
Direct
and
site-selective
C-H
functionalization
of
alkenes
under
environmentally
benign
conditions
represents
a
useful
attractive
yet
challenging
transformation
to
access
value-added
molecules.
Herein,
unified
protocol
for
variety
intermolecular
Heck-type
functionalizations
C
sp2
-H
bond
has
been
developed
by
thianthrenation.
The
reaction
features
metal-free
operationally
simple
exclusive
cine
-selective
aliphatic
aryl
forge
C-C,
C-N,
C-P,
C-S
bonds
at
room
temperature,
providing
general
with
nucleophiles
(Nu
=
sulfinates,
cyanides,
amines,
amides).
Alkenes
undergo
-sulfonylation,
cyanation,
amination
afford
alkenyl
sulfones,
nitriles
enamines.
Chinese Journal of Chemistry,
Journal Year:
2023,
Volume and Issue:
41(16), P. 1979 - 1986
Published: April 5, 2023
Comprehensive
Summary
A
novel
transient
SET
mediator
approach
has
been
developed
for
the
photoinduced
radical‐radical
cross
coupling
reaction.
Using
in‐situ
generated
thianthrene
radical
cation
as
mediator,
thiocyanation
and
selenocyanation
of
aryl
thianthrenium
salts
have
realized
under
mild
conditions
without
need
photocatalyst
or
single
electron
donor.
In
comparison
with
enabled
process,
protocol
features
conditions,
simple
manipulation,
a
broad
substrate
scope,
excellent
functional
group
heterocycle
tolerance.
Due
to
feasible
accessibility
salts,
this
method
also
applied
in
efficient
synthesis
bioactive
molecule,
late‐stage
functionalization
complex
arenes.
Organic Letters,
Journal Year:
2023,
Volume and Issue:
25(12), P. 2162 - 2166
Published: March 21, 2023
The
development
of
mild
methodology
for
converting
inert
C-H
bonds
to
value-added
molecules
has
been
an
attractive
research
topic
during
the
last
few
decades
as
it
offers
efficient
preparation.
Meanwhile,
diaryl
ketones
hold
potent
applications
in
antitumor
drugs,
agrochemical
industry,
and
synthetic
chemistry.
Herein,
we
report
versatile
palladium-catalyzed
carbonylative
cross-coupling
reactions
aryl
thianthrenium
salts
with
arylboronic
acids.
Arenes
were
transformed
site
selectively
via
C(sp2)-H
thianthrenation,
various
desired
produced
good
excellent
yields.
Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(16), P. 3332 - 3337
Published: April 15, 2024
As
a
class
of
rising
electrophilic
coupling
reagents,
aryl–thianthreniums
(aryl-TTs)
have
been
gaining
immense
attention.
Herein,
novel
palladium-catalyzed
domino
annulation
aryl-TTs
with
anhydrides
is
proposed
to
rapidly
assemble
collection
highly
functionalized
fluorenones.
This
finding
presents
an
innovative
reaction
pattern
wherein
the
version
first
involved.
Heavily
compared
existing
conversions
aryl-TTs,
this
identified
process
successively
functions
as
four
aryl
C–H
bonds.
Organic Chemistry Frontiers,
Journal Year:
2024,
Volume and Issue:
11(12), P. 3333 - 3340
Published: Jan. 1, 2024
We
report
a
Pd/NBE
cooperative
catalyzed
ortho
C–H
methylation
and
trideuteromethylation
of
arylthianthrenium
salts,
enabling
the
efficient
synthesis
wide
variety
(trideutero)methylated
arenes
in
moderate
to
good
yields.
Organic Chemistry Frontiers,
Journal Year:
2024,
Volume and Issue:
11(15), P. 4318 - 4342
Published: Jan. 1, 2024
This
review
primarily
focuses
on
the
generation
of
aryl
radicals
via
an
electroreduction
strategy,
and
systematically
elaborates
synthetic
applications,
scope,
limitations
substrates.
Angewandte Chemie International Edition,
Journal Year:
2023,
Volume and Issue:
62(44)
Published: Sept. 13, 2023
Abstract
Efficient
methods
for
synthesizing
1,2‐aryl(alkenyl)
heteroatomic
cores,
encompassing
heteroatoms
such
as
nitrogen,
oxygen,
sulfur,
and
halogens,
are
of
significant
importance
in
medicinal
chemistry
pharmaceutical
research.
In
this
study,
we
present
a
mild,
versatile
practical
photoredox/iron
dual
catalytic
system
that
enables
access
to
highly
privileged
pharmacophores
with
exceptional
efficiency
site
selectivity.
Our
approach
exhibits
an
extensive
scope,
allowing
the
direct
utilization
wide
range
commodity
or
commercially
available
(hetero)arenes
well
activated
unactivated
alkenes
diverse
functional
groups,
drug
scaffolds,
natural
product
motifs
substrates.
By
merging
iron
catalysis
photoredox
cycle,
vast
array
alkene
functionalization
products
incorporate
neighboring
azido,
amino,
halo,
thiocyano
nitrooxy
group
were
secured.
The
scalability
ability
rapid
synthesize
numerous
bioactive
small
molecules
from
readily
starting
materials
highlight
utility
protocol.
