Organic Letters,
Journal Year:
2023,
Volume and Issue:
25(20), P. 3766 - 3771
Published: May 11, 2023
Alkyldiarylsulfonium
salts
were
synthesized
by
a
combination
of
active
sulfonium
species,
prepared
through
the
activation
diarylsulfoxide,
and
alkyl
nucleophiles.
The
isolated
subjected
to
allylation
cyclopropanation
methylene
compounds
metal-free
C(sp3)-C(sp2)
couplings
via
oxyallyl
cation
intermediates
under
mild
conditions.
series
reactions
included
an
umpolung
strategy
for
coupling
nucleophiles
C-C
bond
formation
using
salts.
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.
Chemical Communications,
Journal Year:
2023,
Volume and Issue:
59(36), P. 5343 - 5364
Published: Jan. 1, 2023
The
activation
and
transformation
of
organic
chemical
bonds
is
a
fundamental
scientific
problem.
In
the
past
several
decades,
C-S
bond
cleavage
for
construction
C-C
C-heteroatom
has
received
tremendous
attention
in
chemistry.
Although
significant
progress
been
made
field
transition
metal
strategies,
variety
novel
transition-metal-free
strategies
have
also
developed
using
halogenated
reagents,
oxidants,
acids,
bases.
Moreover,
photochemical
electrochemical
methods
to
achieve
organosulfur
compounds.
To
date,
however,
no
comprehensive
review
reported.
Therefore,
we
herein
provide
major
advances
compounds,
including
thioethers,
sulfoxides,
sulfones,
thioacetals,
sulfonium
salts,
sulfur
ylides.
Chinese Journal of Chemistry,
Journal Year:
2024,
Volume and Issue:
42(15), P. 1679 - 1685
Published: March 15, 2024
Comprehensive
Summary
A
novel
and
eco‐friendly
electrochemical
activation
of
trifluoromethyl
thianthrenium
triflate
(TT–CF
3
+
OTf
−
)
for
trifluoromethylation
imidazole‐fused
heteroaromatic
compounds
was
established.
This
method
involves
the
direct
electrolysis
TT–CF
without
requirement
external
oxidants
or
catalysts,
aligning
with
principles
green
chemistry.
wide
range
including
imidazo[1,2‐
a
]pyridines
benzo[
d
]imidazo[2,1‐
b
]thiazoles
have
been
successfully
trifluoromethylated
using
this
technique,
exhibiting
excellent
compatibility
various
functional
groups
broad
substrate
scope.
Moreover,
method's
applicability
one‐pot
sequential
reactions
enables
reduction
waste
resource
consumption
by
eliminating
need
intermediate
purification
steps.
Angewandte Chemie International Edition,
Journal Year:
2022,
Volume and Issue:
61(39)
Published: Aug. 9, 2022
Here
we
report
an
α-thianthrenium
carbonyl
species,
as
the
equivalent
of
α-carbonyl
carbocation,
which
is
generated
by
radical
conjugate
addition
a
trifluoromethyl
thianthrenium
salt
to
Michael
acceptors.
The
reactivity
allows
for
synthesis
C
Chemical Society Reviews,
Journal Year:
2024,
Volume and Issue:
53(9), P. 4786 - 4827
Published: Jan. 1, 2024
This
review
summarizes
structural
and
synthetic
aspects
of
heterocyclic
molecules
incorporating
an
atom
a
hypervalent
main-group
element.
The
higher
thermal
stability
heterocycles,
as
compared
to
their
acyclic
analogs,
adds
special
feature
chemistry.
Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(9), P. 1980 - 1984
Published: Feb. 29, 2024
Efforts
to
develop
alternatives
triflic
anhydride
(Tf2O)
as
a
trifluoromethylation
reagent
continue
due
its
limitations,
including
volatility,
corrosiveness,
and
moisture
sensitivity.
Described
herein
is
the
use
of
trifluoromethylsulfonylpyridinium
salt
(TFSP),
easily
obtained
by
one-step
reaction
Tf2O
with
4-dimethylaminopyridine,
for
trifluoromethylative
difunctionalization
alkenes
photoredox
catalysis.
DMSO
CH3CN
are
suitable
solvents
achieving
keto-
amino-trifluoromethylation
alkenes,
respectively,
good
functional
group
tolerance.
Organic Letters,
Journal Year:
2023,
Volume and Issue:
25(36), P. 6633 - 6637
Published: Sept. 6, 2023
Herein,
we
report
a
light-driven,
radical-type
cyano
migration
in
the
absence
of
photocatalyst,
enabling
chemo-divergent
synthesis
(Z)-alkenyl
nitriles
and
ketones.
Trifluoromethyl
thianthrenium
salt
(TT–CF3+OTf–)
plays
multiple
roles:
(a)
absorbing
light
to
generate
trifluoromethyl
radicals
initiate
reaction
(b)
forming
α-thianthrenium
species
by
situ
capture
TT•
+.
(Z)-Alkenyl
were
formed
through
elimination
salts,
aryl
ketones
obtained
via
nucleophilic
substitution
salts.
Chemistry - A European Journal,
Journal Year:
2024,
Volume and Issue:
30(18)
Published: Jan. 6, 2024
Hydroxytrifluoroethyl
and
trifluoroacetyl
groups
are
of
utmost
importance
in
biologically
active
compounds,
but
methods
to
tether
these
motifs
organic
architectures
have
been
limited.
Typically,
the
preparation
compounds
relied
on
use
strong
bases
or
multistep
routes.
The
renaissance
radical
chemistry
photocatalytic,
transition
metal
mediated,
hydrogen
atom
transfer
(HAT)
processes
allowed
installation
medicinally
relevant
fluorinated
motifs.
This
review
provides
an
overview
available
for
direct
synthesis
hydroxytrifluoroethyl-
trifluoroacetyl-derived
governed
by
single-electron
processes.
Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(20), P. 4388 - 4393
Published: May 16, 2024
Herein,
a
photoredox-driven
practical
protocol
for
fluorinated
alkene
synthesis
using
easily
accessible
and
modular
thianthrenium
salts
with
electron-withdrawing
alkynes
or
propargyl
alcohols
is
reported.
Vinyl
radical
intermediates,
formed
by
the
reaction
between
alkyl
trifluoromethyl
electronically
diverse
alkynes,
can
mediate
key
1,5-HAT
process
of
regioselective
C(sp3)–H
fluorination
vinylation.
This
provides
straightforward
access
to
structurally
trifluoromethyl-
distally
fluoro-functionalized
products
in
21–79%
yields
broad
substrate
range
under
mild
photocatalytic
conditions.
