Organic Letters,
Год журнала:
2024,
Номер
26(10), С. 2108 - 2113
Опубликована: Март 5, 2024
A
metal-free
photosensitized
1,2-imino-sulfamoylation
of
olefins
by
employing
a
tailor-made
sulfamoyl
carbamate
as
the
difunctionalization
reagent
has
been
established.
This
protocol
exhibits
versatility
across
broad
substrate
scope,
including
aryl
and
aliphatic
alkenes,
leading
to
synthesis
diverse
β-imino
sulfonamides
in
moderate
good
yields.
method
is
characterized
its
reaction
system,
mild
conditions,
excellent
regioselectivity,
high
atom
economy,
serving
promising
platform
for
preparation
β-amino
sulfonamide-containing
molecules,
particularly
context
drug
discovery.
Organic Letters,
Год журнала:
2023,
Номер
25(9), С. 1595 - 1599
Опубликована: Фев. 24, 2023
A
vinyl
radical-mediated
1,5-hydrogen
atom
transfer
strategy
for
remote
C(sp3)-H
imination
under
visible-light-induced
photochemical
metal-free
conditions
afforded
diverse
γ-imino
alkenes
with
excellent
stereoselectivity.
Oxime
ester-based
bifunctional
reagents
provided
not
only
nucleophilic
alkyl
radicals
radical
addition
reactions
electron-deficient
alkynes
but
also
long-lived
steady-state
imine
trapping
following
the
intramolecular
migration
of
unstable
olefin
radicals.
ACS Catalysis,
Год журнала:
2024,
Номер
14(17), С. 13343 - 13351
Опубликована: Авг. 22, 2024
Atomic
carbon
and
its
corresponding
masked
analogues
are
exceedingly
underexplored
intermediates
in
synthesis.
Despite
this,
these
reagents
possess
inimitable
reactivity
such
as
the
ability
to
directly
insert
atoms
into
aromatic
frameworks
while
simultaneously
generating
an
additional
bond
at
center
further
diversify
structure.
Herein,
we
report
design
of
orthogonally
reactive
atomic
equivalent
Cl-DADO
demonstrate
application
molecular
editing
indole
pyrrole,
accessing
linchpin-containing
ring-expanded
heterocycles
that
can
be
subsequently
derivatized.
The
value
this
approach
broad
applicability
reagent
highlighted
by
late-stage
skeletal
numerous
natural
products
drug
molecules.
Angewandte Chemie International Edition,
Год журнала:
2024,
Номер
63(8)
Опубликована: Янв. 5, 2024
Abstract
Dearomative
spirocyclization
reactions
represent
a
promising
means
to
convert
arenes
into
three‐dimensional
architectures;
however,
controlling
the
regioselectivity
of
radical
dearomatization
with
nonactivated
afford
spirocyclizative
1,2‐difunctionalization
other
than
its
kinetically
preferred
1,4‐difunctionalization
is
exceptionally
challenging.
Here
we
disclose
novel
strategy
for
dearomative
1,2‐
or
1,4‐amidoximation
(hetero)arenes
enabled
by
direct
visible‐light‐induced
homolysis
N−NO
bonds
nitrosamides,
giving
rise
various
highly
regioselective
amidoximated
spirocycles
that
previously
have
been
inaccessible
required
elaborate
synthetic
efforts.
The
mechanism
and
origins
observed
regioselectivities
were
investigated
control
experiments
density
functional
theory
calculations.
Organic Letters,
Год журнала:
2024,
Номер
26(10), С. 2108 - 2113
Опубликована: Март 5, 2024
A
metal-free
photosensitized
1,2-imino-sulfamoylation
of
olefins
by
employing
a
tailor-made
sulfamoyl
carbamate
as
the
difunctionalization
reagent
has
been
established.
This
protocol
exhibits
versatility
across
broad
substrate
scope,
including
aryl
and
aliphatic
alkenes,
leading
to
synthesis
diverse
β-imino
sulfonamides
in
moderate
good
yields.
method
is
characterized
its
reaction
system,
mild
conditions,
excellent
regioselectivity,
high
atom
economy,
serving
promising
platform
for
preparation
β-amino
sulfonamide-containing
molecules,
particularly
context
drug
discovery.
