Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(6), P. 1178 - 1183
Published: Feb. 2, 2024
Sulfoximines
and
pyrazoles
are
both
important
motifs
in
medicinal
compounds.
Here
we
report
the
synthesis
reactivity
of
sulfoximine
diazo
compounds
as
new
reagents
for
incorporation
sulfoximines.
The
use
N-silyl
sulfoximines
enabled
formation
monosubstituted
Their
application
is
demonstrated
a
[3
+
2]
cycloaddition
with
alkynes
to
form
pyrazole
combination
these
chemotypes.
Further
derivatization
demonstrated,
including
silyl
deprotection
unprotected
pyrazolesulfoximines.
We
report
a
modular
photoredox
strategy
for
the
synthesis
of
aryl
vinyl
sulfoximines
from
sulfinamide
and
halide
starting
materials.
This
demonstrates
difunctionalization
sulfinamides
to
sulfoximine
products
with
excellent
configurational
retention
stereoselective
trans
alkenes.
Under
mild
redox
conditions,
we
propose
generation
nitrogen
centered
radical
that
is
resonance
stabilized
by
sulfur
partner,
increasing
overall
lifetime.
disclose
thus
well
suited
capture,
leading
products.
process
also
entails
broad
modularity
about
alkene,
arene,
acyl
protecting
group,
providing
synthetic
chemists
multiple
functional
handles
allowing
further
exploration
into
physicochemical
properties
have
shown
promise
in
recent
studies.
