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.
Angewandte Chemie International Edition,
Год журнала:
2024,
Номер
63(38)
Опубликована: Июнь 26, 2024
A
modular
synthesis
of
sulfondiimidoyl
fluorides-the
double
aza-analogues
sulfonyl
fluorides-allowing
variation
the
carbon
and
both
nitrogen-substituents
is
reported.
The
chemistry
uses
readily
available
organometallic
reagents,
commercial
sulfinylamines,
simple
electrophiles,
N-fluorobenzenesulfonimide
(NFSI),
as
starting
materials.
reactions
are
broad
in
scope,
efficient,
scalable.
We
show
that
fluoride
products
can
be
combined
with
amines
to
provide
sulfondiimidamides,
organolithium
reagents
sulfondiimines,
reactivity
these
transformations
modulated
by
N-substituents.
Journal of the American Chemical Society,
Год журнала:
2024,
Номер
unknown
Опубликована: Дек. 12, 2024
Four-membered
heterocycles
such
as
oxetanes
and
azetidines
represent
attractive
emergent
design
options
in
medicinal
chemistry
due
to
their
small
polar
nature
potential
significantly
impact
the
physiochemical
properties
of
drug
molecules.
The
challenging
preparation
these
derivatives,
especially
a
divergent
manner,
has
severely
limited
combination
with
other
medicinally
biologically
important
groups.
Consequently,
there
is
substantial
demand
for
mild
effective
synthetic
strategies
access
new
oxetane
azetidine
derivatives
molecular
scaffolds.
Here,
we
report
development
use
sulfonyl
fluorides
(OSFs)
(ASFs),
which
behave
precursors
carbocations
an
unusual
defluorosulfonylation
reaction
pathway
(deFS).
small-ring
are
activated
under
thermal
conditions
(60
°C),
generated
reactive
intermediates
couple
broad
range
nucleophiles.
Oxetane
heterocyclic,
-sulfoximine,
-phosphonate
prepared,
several
do
not
have
comparable
carbonyl
analogs,
providing
chemical
motifs
elements
discovery.
Alternatively,
SuFEx
anionic
accesses
oxetane-sulfur(VI)
derivatives.
We
demonstrate
utility
novel
OSF
ASF
reagents
through
synthesis
11
showcasing
subsequent
diversification
facile
inclusion
into
programs.
Moreover,
propose
application
linker
incorporation
pendant
groups
suitable
common
conjugation
reactions.
Productive
deFS
reactions
E3
ligase
recruiters
pomalidomide
related
provide
degrader
PROTAC
linkers.
Organic & Biomolecular Chemistry,
Год журнала:
2023,
Номер
21(37), С. 7597 - 7601
Опубликована: Янв. 1, 2023
An
efficient
metal-free
visible-light-mediated
protocol
for
the
synthesis
of
various
aryl
sulfonyl
fluorides
from
diaryliodonium
salts
via
a
radical
sulfur
dioxide
insertion
and
fluorination
strategy
was
developed.
Organic Letters,
Год журнала:
2024,
Номер
26(46), С. 9897 - 9902
Опубликована: Ноя. 9, 2024
A
new
method
uses
metal
Lewis
acids
as
catalysts
to
convert
sulfonyl
fluorides,
fluorosulfates,
and
sulfamoyl
fluorides
with
silyl
amines
into
S-N
bond-containing
compounds
via
sulfur
fluoride
exchange.
The
reaction
successfully
employs
Ca(NTf
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.
