Organic Letters,
Год журнала:
2024,
Номер
26(17), С. 3661 - 3666
Опубликована: Апрель 24, 2024
Considering
the
ubiquitous
presence
of
pyridine
moieties
in
pharmaceutical
compounds,
it
holds
immense
value
to
develop
practical
and
straightforward
methodologies
for
accessing
heterocyclic
aromatic
hydrocarbons.
In
recent
years,
N-alkoxypyridinium
salts
have
emerged
as
convenient
radical
precursors,
enabling
generation
corresponding
alkoxy
radicals
through
single-electron
transfer.
Herein,
we
present
first
report
on
visible-light-mediated
intermolecular
alkoxypyridylation
alkenes
employing
N-alkoxylpyridinium
bifunctional
reagents
with
an
exceptionally
low
catalyst
loading
(0.5
mol
%).
The Journal of Organic Chemistry,
Год журнала:
2023,
Номер
89(1), С. 644 - 655
Опубликована: Дек. 13, 2023
A
photoredox-catalyzed
intermolecular
tandem
sulfonamination/cyclization
of
enaminones
was
realized
by
using
N-aminopyridinium
salts
as
the
sulfonaminated
reagents
without
transition-metal
catalysts
or
bases.
The
reaction
exhibits
a
broad
scope
and
good
functional
group
tolerance,
yields,
regioselectivity.
Preliminary
mechanistic
studies
support
radical
property
involvement
N-centered
intermediates.
Advanced Synthesis & Catalysis,
Год журнала:
2024,
Номер
366(9), С. 2003 - 2007
Опубликована: Март 12, 2024
Abstract
A
DBU‐promoted
[3+2]
cyclization/retro‐Mannich
cascade
reaction
of
N
‐aminoisoquinolinium
and
‐aminoquinolinium
derivatives
with
para
‐quinone
methides
has
been
established,
employing
a
C=C
double
bond
cleavage.
broad
range
salts,
are
well
tolerated,
providing
the
corresponding
rearrangement
products.
Moreover,
scaled‐up
reactions
diverse
derivatizations
products
were
also
investigated
discussed.
Advanced Synthesis & Catalysis,
Год журнала:
2024,
Номер
366(9), С. 2072 - 2078
Опубликована: Март 1, 2024
Abstract
A
photoinduced
direct
synthesis
of
3‐amino‐1‐indenones
via
radical
cascade
cyclization
strategy
is
demonstrated.
The
methodology
involves
a
domino
reaction
between
2‐alkynylarylnitrile
and
N
‐aminopyridinium
salt
captures
the
reactivity
in‐situ
generated
nitrogen‐centered
(NCR)
in
visible
light.
Multiple
bond‐forming
events
including
C−N,
C−C,
C−O
take
place
sequentially
on
enabling
construction
3‐amino‐1‐indenone
core
at
room
temperature
35–76%
yield.
preliminary
biological
screening
synthesized
compounds
indicative
their
potent
anti‐cancer
property.
European Journal of Organic Chemistry,
Год журнала:
2024,
Номер
27(19)
Опубликована: Март 21, 2024
Abstract
Herein,
visible‐light‐induced
metal‐free
three‐component
amidoheteroarylation
of
alkenes
with
quinoxalin‐2(1
H
)‐ones
and
N‐sulfonylaminopyridinium
salts
is
developed.
This
protocol
involves
a
radical
relay
process
in
which
the
N‐centered
radicals
undergo
chemoselective
addition
to
form
an
alkyl
that
selectively
combines
heteroarenes,
leading
formation
C−C
C−N
bonds
one
step
under
mild
reaction
conditions.
The
involved
high
efficiency
selectivity,
wide
substrate
scope,
excellent
functional‐group
compatibility
demonstrate
practicability
developed
protocol.
Organic & Biomolecular Chemistry,
Год журнала:
2024,
Номер
22(29), С. 5897 - 5901
Опубликована: Янв. 1, 2024
Sulfonyl
groups
are
motifs
that
widely
found
in
biologically
active
compounds
and
drug
molecules,
many
isolated
natural
products
as
well
pharmaceuticals
contain
sulfonyl
groups.
Herein,
we
present
the
synthesis
of
sulfonyl-substituted
isoindolones
by
a
electrochemical
oxidative
radical
cascade
cycloaddition
reaction
olefinic
amides
with
sodium
sulfite
under
oxidant-
catalyst-free
conditions.
Various
sulfinates
were
compatible
gave
desired
yields
up
to
99%.
RSC Advances,
Год журнала:
2025,
Номер
15(5), С. 3273 - 3277
Опубликована: Янв. 1, 2025
A
copper-catalyzed
oxygen
trifluoromethylation
of
o
-vinyl-
N
-alkylamide
using
Togni
reagent
as
the
trifluoromethyl
precursor
is
demonstrated
for
efficient
synthesis
trifluoromethyl-containing
iminoisobenzofurans.
The Journal of Organic Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Апрель 22, 2025
A
visible-light-driven
intermolecular
tandem
α-amidotrifluoroethylation/cyclization
of
enaminones
using
a
previously
unreported
N-trifluoroethylaminopyridinium
salt
was
achieved
in
the
absence
transition
metal
catalysts
or
bases.
Notable
features
this
synthetic
method
include
mild
conditions,
high
selectivity,
excellent
functional
group
compatibility,
and
satisfactory
yields.
Preliminary
mechanistic
studies
indicate
that
reaction
proceeds
via
radical
pathway,
involving
an
situ
generated
N-trifluoroethyl
radical,
followed
by
1,2-H
shift.
