We
herein
report
a
photochemical
Truce–Smiles
rearrangement
reaction
of
N-sulfinyl
acrylamides
with
bromodifluoroacetamides
resulting
in
the
synthesis
series
aryl
difluoroglutaramides
moderate
to
good
yields.
The
asymmetric
using
chiral
sulfinamides
produced
quaternary
carbon-centered
glutaramide
products
modest
enantioselectivity.
This
protocol
effectively
complements
previous
methods
involving
N-sulfonyl
acrylamides.
Advanced Synthesis & Catalysis,
Год журнала:
2024,
Номер
366(6), С. 1325 - 1330
Опубликована: Фев. 2, 2024
Abstract
Copper‐catalyzed
silylarylation
of
N
‐(arylsulfonyl)acrylamides
via
a
tandem
silyl
radical
addition/1,4‐aryl
migration/desulfonylation
sequence
has
been
developed.
This
method
employs
silanes
as
the
precursor
and
di‐
tert
‐butyl
peroxide
(DTBP)
initiator.
By
using
this
cascade
procedure,
series
β
‐silyl
amide‐pharmaceutical
hybrids
which
contain
an
α
‐all‐carbon
quaternary
stereocenter
were
facilely
synthesized.
Green Chemistry,
Год журнала:
2024,
Номер
26(11), С. 6774 - 6778
Опубликована: Янв. 1, 2024
A
novel
and
attractive
photochemical
difunctionalization
of
N
-tosyl
acrylamide
for
constructing
alkylsulfonylated
oxindoles
amides
with
excellent
substrate
adaptability
via
a
radical
Smiles
rearrangement
strategy
is
described.
Organic Letters,
Год журнала:
2023,
Номер
25(51), С. 9186 - 9190
Опубликована: Дек. 15, 2023
The
photoredox/PPh3-mediated
cyclization
of
2-isocyanobiaryls
has
been
developed.
A
substantial
range
functional-group-rich
phenanthridine
derivatives
were
synthesized
at
room
temperature
in
a
highly
selective
and
atom-economic
manner.
Mechanistic
studies
suggested
that
the
process
is
probably
mediated
both
by
Ph3P
radical
cation
with
key
1,2-hydride
transfer
hydrogen
atom
generated
through
O–H
bond
homolytic
cleavage
Ph3P–OH
intermediate.
Angewandte Chemie International Edition,
Год журнала:
2025,
Номер
unknown
Опубликована: Янв. 2, 2025
The
azidofunctionalization
of
alkenes
under
mild
conditions
using
commercially
available
starting
materials
and
easily
accessible
reagents
is
reported
based
on
a
radical-polar
crossover
strategy.
A
broad
range
alkenes,
including
vinyl
arenes,
enamides,
enol
ethers,
sulfides,
dehydroamino
esters,
were
regioselectively
functionalized
with
an
azide
nucleophiles
such
as
azoles,
carboxylic
acids,
alcohols,
phosphoric
oximes,
phenols.
method
led
to
more
efficient
synthesis
1,2-azidofunctionalized
pharmaceutical
intermediates
when
compared
previous
approaches,
resulting
in
both
reduction
step
count
increase
overall
yield.
scope
limitations
these
transformations
further
investigated
through
standard
unbiased
selection
15
substrate
combinations
out
1,175,658
possible
clustering
technique.
Angewandte Chemie,
Год журнала:
2025,
Номер
unknown
Опубликована: Янв. 2, 2025
Abstract
The
azidofunctionalization
of
alkenes
under
mild
conditions
using
commercially
available
starting
materials
and
easily
accessible
reagents
is
reported
based
on
a
radical‐polar
crossover
strategy.
A
broad
range
alkenes,
including
vinyl
arenes,
enamides,
enol
ethers,
sulfides,
dehydroamino
esters,
were
regioselectively
functionalized
with
an
azide
nucleophiles
such
as
azoles,
carboxylic
acids,
alcohols,
phosphoric
oximes,
phenols.
method
led
to
more
efficient
synthesis
1,2‐azidofunctionalized
pharmaceutical
intermediates
when
compared
previous
approaches,
resulting
in
both
reduction
step
count
increase
overall
yield.
scope
limitations
these
transformations
further
investigated
through
standard
unbiased
selection
15
substrate
combinations
out
1,175,658
possible
clustering
technique.
Organic & Biomolecular Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Янв. 1, 2025
We
present
a
photoredox
nickel-catalyzed
intermolecular
cyclization
between
N
-arylacrylamides
and
readily
accessible
alkyl
bromides,
which
affords
diverse
range
of
3,3-disubstituted
oxindoles
in
moderate
to
high
yields.
JACS Au,
Год журнала:
2024,
Номер
4(7), С. 2456 - 2461
Опубликована: Июнь 17, 2024
A
domino
difunctionalization
of
sulfonyl(acryl)imides
to
form
β-substituted
α-aryl
amides
is
reported.
This
transformation
involves
a
1,4-addition
followed
by
polar
Truce-Smiles
rearrangement
process,
entropically
driven
release
SO
Chinese Journal of Chemistry,
Год журнала:
2024,
Номер
42(19), С. 2323 - 2328
Опубликована: Май 22, 2024
Comprehensive
Summary
A
novel
visible‐light‐induced
radical
cascade
6‐
endo
cyclization
of
dienes
(
N
‐(2‐vinylphenyl)acryl
amides)
is
developed
utilizing
α‐carbonyl
bromides
as
alkyl
reagents.
This
approach
affords
an
efficient
way
for
synthesizing
six‐membered
benzo‐fused
lactam
derivatives
with
chemo‐
and
regio‐selectivity
good
functional
group
tolerance.
Primary,
secondary,
tertiary
are
well‐compatible
this
reaction.
The Journal of Organic Chemistry,
Год журнала:
2023,
Номер
88(24), С. 17511 - 17520
Опубликована: Ноя. 29, 2023
Despite
the
widespread
applications
of
sulfoximines,
green
and
efficient
access
to
functionalized
sulfoximines
remains
a
challenge.
By
employing
an
electrochemical
strategy,
we
describe
approach
for
construction
N-aroylsulfoximines,
which
features
broad
substrate
scope,
mild
reaction
conditions,
safety
on
gram
scale,
no
need
external
oxidant
transition
metal
catalysts.
