Encyclopedia of Reagents for Organic Synthesis,
Год журнала:
2024,
Номер
unknown, С. 1 - 6
Опубликована: Апрель 18, 2024
image
A
[
195072‐48‐1
]
C
19
H
13
F
3
O
S
(MW
442.48)
InChI
=
1S/C18H13S2.CHF3O3S/c1‐2‐8‐14(9‐3‐1)20‐17‐12‐6‐4‐10‐15(17)19‐16‐11‐5‐7‐13‐18(16)20;2‐1(3,4)8(5,6)7/h1‐13H;(H,5,6,7)/q+1;/p‐1
InChiKey
ILICKJZOLUIMMN‐UHFFFAOYSA‐M
B
2839478‐51‐0
20
14
ClF
4
506.95)
1S/C19H14ClOS2.CHF3O3S/c1‐21‐15‐11‐10‐13(12‐14(15)20)23‐18‐8‐4‐2‐6‐16(18)22‐17‐7‐3‐5‐9‐19(17)23;2‐1(3,4)8(5,6)7/h2‐12H,1H3;(H,5,6,7)/q+1;/p‐1
UHXRBIHFIKXURP‐UHFFFAOYSA‐M
2786722‐96‐9
12
6
510.48)
1S/C19H12F3S2.CHF3O3S/c20‐19(21,22)13‐9‐11‐14(12‐10‐13)24‐17‐7‐3‐1‐5‐15(17)23‐16‐6‐2‐4‐8‐18(16)24;2‐1(3,4)8(5,6)7/h1‐12H;(H,5,6,7)/q+1;/p‐1
UEAVFAKSNUECER‐UHFFFAOYSA‐M
D
2786723‐55‐3
18
NO
443.47)
1S/C17H12NS2.CHF3O3S/c1‐3‐7‐16‐14(5‐1)19‐15‐6‐2‐4‐8‐17(15)20(16)13‐9‐11‐18‐12‐10‐13;2‐1(3,4)8(5,6)7/h1‐12H;(H,5,6,7)/q+1;/p‐1
SRMXRMTYQFMLCQ‐UHFFFAOYSA‐M
(reagents
used
as
an
aryl
pseudohalide
in
transition‐metal
catalyzed,
transition
metal‐free,
and
photochemical
reactions)
Physical
Data
:
mp
202.8–204.7
°C.
1
159.2–162.7
2
(Not
reported).
A–D
Solubility
soluble
acetonitrile
dichloromethane.
–
Form
Supplied
not
commercially
available;
free‐flowing
solids
prepared
by
literature
procedures.
3–5
Analysis
of
Reagent
Purity
NMR.
Purification
trituration
from
dichloromethane
using
diethyl
ether
or
hexanes;
silica
gel
chromatography
(eluting
with
DCM:MeOH).
Handling,
Storage,
Precautions
stable
under
ambient
conditions
for
extended
periods
time.
Can
be
weighed
normal
atmosphere
stored
a
vial
air.
Preparative
Methods
(From
simple
arenes)
Treatment
thianthrene
‐oxide
(TTSO)
trifluoroacetic
anhydride
(TFAA)
triflic
acid
(TfOH)
the
presence
desired
arene
at
0
After
addition
all
reagents,
reactions
are
typically
allowed
to
stir
between
h
depending
on
substrate.
Alternatively,
treatment
TTSO
(Tf
O)
−40
3,5
completion,
purple
reaction
is
quenched
methanol
generate
colorless/yellow
solution.
The
crude
mixture
concentrated
reduced
pressure
residue
triturated
afford
solid
which
isolated
filtration.
arylboronic
acids)
thianthrene,
copper(II)
triflate
water
nitrogen
100
°C
h.
aqueous
workup,
Angewandte Chemie International Edition,
Год журнала:
2024,
Номер
63(30)
Опубликована: Май 7, 2024
Abstract
Site‐selective
ortho/ipso
C−H
difunctionalizations
of
aromatic
compounds
were
designed
to
afford
polyfunctionalized
arenes
including
challenging
1,2,3,4‐tetrasubstituted
ones
(62
examples,
up
97
%
yields).
To
ensure
the
excellent
regioselectivity
process
while
keeping
high
efficiency,
an
original
strategy
based
on
a
“C−H
thianthenation/Catellani‐type
reaction”
sequence
was
developed
starting
from
simple
arenes.
Non‐prefunctionalized
first
regioselectively
converted
into
corresponding
thianthrenium
salts.
Then,
palladium‐catalyzed,
norbornene
(NBE)‐mediated
allowed
synthesis
ipso
‐olefinated/
ortho
‐alkylated
using
thianthrene
as
leaving
group
(revisited
Catellani
reaction).
Pleasingly,
commercially
available
(NBE)
and
unique
catalytic
system,
synthetic
challenges
known
for
reaction
with
aryl
iodides
smoothly
successfully
tackled
“thianthrenium”
approach.
The
protocol
robust
(gram‐scale
reaction)
widely
applied
two‐fold
functionalization
various
bio‐active
compounds.
Moreover,
panel
olefins
alkyl
halides
coupling
partners
suitable.
further
incorporation
other
groups
at
(CN/alkyl/H,
aryl)
(alkyl,
aryl,
amine,
thiol)
positions,
showcasing
generality
process.
Molecules,
Год журнала:
2024,
Номер
29(9), С. 1991 - 1991
Опубликована: Апрель 26, 2024
An
efficient
palladium-catalyzed
carbonylation
of
aryl
fluorosulfates
with
formates
for
the
facile
synthesis
esters
was
developed.
The
cross-coupling
reactions
proceeded
effectively
in
presence
a
palladium
catalyst,
phosphine
ligand,
and
triethylamine
DMF
to
produce
corresponding
moderate
good
yields.
Of
note,
functionalities
or
substituents,
such
as
nitro,
cyano,
methoxycarbonyl,
trifluoromethyl,
methylsulfonyl,
trifluoromethoxy,
fluoro,
chloro,
bromo,
methyl,
methoxy,
N,N-dimethyl,
[1,3]dioxolyl,
were
well-tolerated
reactions,
which
could
be
kept
late-stage
modification.
employing
readily
available
relatively
robust
coupling
electrophiles
potentially
serve
an
attractive
alternative
traditional
cross-couplings
use
halides
pseudohalides
substrates.
Organic Letters,
Год журнала:
2023,
Номер
25(15), С. 2606 - 2610
Опубликована: Апрель 11, 2023
The
mild
and
efficient
palladium-catalyzed
pyrrolidin-2-yl
tetrahydrofuran-2-yl
methylation
of
(hetero)arenes
has
been
developed.
A
wide
range
underwent
the
regioselective
thianthrenation
to
generate
arylthianthrenium
triflate,
developed
Pd-catalyzed
alkene
carboamination
carboalkoxylation
reactions
afforded
corresponding
biologically
important
pyrrolidine
tetrahydrofuran
derivatives.
Mechanistic
studies
indicated
that
this
reaction
proceeds
through
a
syn-heteropalladation
mechanistic
pathway.
demonstrated
late-stage
functionalization
enantioselective
will
help
promote
potential
application
established
method
in
organic
synthesis
related
fields.
A
nickel-catalyzed
site-selective
reductive
carbonylation
of
arenes
via
aryl
thianthrenium
salts
is
described.
Using
Mo(CO)6
as
a
convenient
solid
CO
source
and
reductant
employing
nitroarenes
sulfonyl
chlorides
readily
available
nitrogen
sulfur
sources,
range
amides
thioesters
were
successfully
synthesized
in
moderate
to
good
yields.
The
utility
this
transformation
demonstrated
through
the
synthesis
antimicrobial
agents
late-stage
functionalization
biorelevant
molecules.
European Journal of Organic Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Июнь 3, 2025
A
simple
aryl–aryl
bond‐forming
reaction
via
palladium‐catalyzed
cross‐coupling
between
cheap
and
easily
accessible
arene
carboxylic
acids
aryl
thianthrenium
trifluoromethanesulfonates
is
described.
It
turns
out
that
the
use
of
PdCl
2
in
presence
Ag
CO
3
DMSO
at
120
°C
most
efficient
system
for
performing
this
reaction.
Various
biaryls,
bearing
electron‐donating
or
electron‐withdrawing
groups,
including
sterically
hindered
biaryls
are
successfully
obtained.
The
amount
waste
generated
during
minimized
since
thianthrene
obtained
as
a
by‐product
can
be
recovered
reused
after
