Synthetic Communications,
Год журнала:
2023,
Номер
53(21), С. 1784 - 1798
Опубликована: Авг. 22, 2023
AbstractA
visible-light-mediated
fluorosulfonylation
reaction
of
thianthrenium
salts
has
been
developed
to
prepare
various
sulfonyl
fluorides
with
1,4-diazabicyclo
[2.2.2]
octane
bis
(sulfur
dioxide)
(DABSO)
as
source
and
cheap
KHF2
fluorine
based
on
radical
sulfur
dioxide
insertion
fluorination
strategy.
This
operationally
simple
protocol
proceeds
high
functional-group
tolerance
under
mild
conditions.Keywords:
Fluorosulfonylationthianthrenium
saltsvisible-light-mediated
Disclosure
statementNo
potential
conflict
interest
was
reported
by
the
author(s).Additional
informationFundingThe
authors
gratefully
acknowledge
financial
support
from
National
Natural
Science
Foundation
China
[No.
21871283],
project
Technology
Commission
Shanghai
Municipality
in
[21010503800],
Key
Laboratory
Organofluorine
Chemistry,
Institute
Organic
Chinese
Academy
Sciences,
Engineering
Research
Center
Green
Fluoropharmaceutical
Technology,
Technology.
A
radical
fluorosulfonylation
of
allyl
bromides
was
achieved
under
electroreductive
conditions.
This
catalyst-free
protocol
employs
mild
conditions
and
enables
straightforward
access
to
a
new
structurally
diverse
variety
previously
inaccessible
sulfonyl
fluorides.
We
have
also
illustrated
the
synthetic
value
this
method
by
performing
scaled-up
reactions
product
derivatization.
Herein,
we
describe
the
successful
development
of
an
azido-fluorosulfonylation
reaction
alkenes
under
photoredox
catalysis,
which
could
allow
installation
two
"clickable"
groups,
-N3
and
-SO2F,
on
a
C-C
double
bond,
with
TMSN3
as
azide
source.
The
utilization
difunctionalization
products
is
also
demonstrated
in
construction
library
1,2,3-triazolesulfonyl
fluoride
compounds
well
drug
molecule
ligation
by
merging
copper-catalyzed
azide-alkyne
cycloaddition
(CuAAC)
sulfur(VI)
exchange
(SuFEx),
generations
click
reactions.
Mechanistic
studies
suggest
radical
fluorosulfonylation/azidation
mechanism
unveil
FSO2N3
new
potential
fluorosulfonyl
precursor.
The
sulfonyl
group
is
able
to
polarize
adjacent
C=C
bonds,
but
strength
of
the
effect
considerably
varies
with
substituents
(SO2X).
In
this
report,
we
present
asymmetric
organocatalyzed
conjugate
addition
1,3-dicarbonyl
compounds
β-arylvinyl
triflones
(ArCH=CHSO2CF3).
reaction
runs
under
mild
conditions
5
mol
%
tertiary
amino-thiourea
afford
Michael-type
adducts
in
high
yields
and
enantioselectivities.
Comparative
experiments
reveal
that
electron-withdrawing
properties
increase
series
SO2F
≪
SO2CF3
<
SO2C4F9,
latter
approaching
nitro
group.
Mechanochemical
S(VI)
exchange
reactions
are
developed
on
chiral
S(VI)–F
and
S(VI)–Cl
centers
that
fast,
solvent–free,
high–yielding,
enantiospecific.
This
approach
is
used
to
synthesize
a
range
of
sulfonimidate
esters
sulfonimidamides
from
sulfonimidoyl
fluorides
chlorides
under
mild
reaction
conditions.
The
broad
scope
this
method
demonstrated
by
its
successful
reactivity
with
phenols
both
primary
secondary
anilines.
Furthermore,
substitution
in
4–nitrophenol‐derived
species
substituted
(SuPhenEx)
successfully
achieved.
faster,
greener,
reduces
the
need
for
formation
fluorinated
species,
while
retaining
many
advantages
SuFEx
related
reactions.
Research Journal of Pharmacy and Technology,
Год журнала:
2025,
Номер
unknown, С. 831 - 838
Опубликована: Фев. 27, 2025
Over
the
last
four
dacades,
obesity
has
emerged
as
a
significant
globale
health
issue,
closely
associated
with
several
serious
condition
including
diabetes
and
heart
diseases.
Alarmingly,
prevalence
of
continues
to
rise
each
year,
effective
solutions
seem
elusive.
While
various
strategies
medications
have
been
introduced
tackle
support
weight
loss;
many
these
options
come
drawbacks,
such
risk
malnutrition
inconsistent
results
due
limited
effectiveness.
In
this
study,
we
will
adopt
molecular
modelling
approach
using
pharmacophore
based
virtual
screening
docking
studies
design
potential
oral
pancreatic
lipase
inhibitors
which
prevent
excess
fatty
acid
absorption
promotes
loss,
all
while
minimizing
intestinal
avoid
possible
systemic
side
effects.
Organic & Biomolecular Chemistry,
Год журнала:
2023,
Номер
21(18), С. 3789 - 3793
Опубликована: Янв. 1, 2023
We
developed
an
efficient
palladium-catalyzed
fluorosulfonylation
reaction
of
aryl
thianthrenium
salts
to
smoothly
prepare
various
sulfonyl
fluorides
using
cheap
Na2S2O4
as
a
convenient
source
in
combination
with
N-fluorobenzenesulfonimide
(NFSI)
ideal
fluorine
under
mild
reduction
conditions.
A
one-pot
synthesis
starting
from
arenes
was
established
well
without
the
need
for
separating
salts.
The
practicality
this
protocol
demonstrated
by
gram-scale
synthesis,
derivatization
reactions,
and
excellent
yields.
Organic Letters,
Год журнала:
2023,
Номер
25(33), С. 6222 - 6227
Опубликована: Авг. 15, 2023
Herein
we
report
the
facile
syntheses
of
tetrazoles
enabled
by
FSO2N3
under
mild
conditions.
has
been
shown
as
most
powerful
diazotizing
reagent,
which
converts
thousands
primary
amines
to
azides
fast
and
orthogonally.
As
follow-up
studies
diazo
transfer
reaction
using
FSO2N3,
discover
that
amidines
guanidines
are
rapidly
transformed
into
tetrazole
derivatives
when
reacting
with
an
aqueous
environment,
is
unprecedented
for
synthesis.
