European Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
unknown
Published: Dec. 12, 2024
Abstract
Nitrogen‐centered
radicals
(NCRs)
have
gained
significant
attention
due
to
their
high
reactivity,
which
facilitates
many
useful
and
challenging
transformations,
particularly
in
the
formation
of
C−N
bonds.
In
this
regard,
N
‐aminopridinium
reagents
are
easily
accessible
substrates
that
readily
generate
‐centered
radicals,
can
be
trapped
by
arenes,
olefins,
alkynes
even
alkanes
under
visible
light
irradiation.
recent
years,
amination
strategies
involving
‐aminopyridinium
salts
grown
remarkably
attracted
considerable
interest
within
synthetic
community.
This
review
comprehensively
includes
all
advances
bond
construction
via
derived
from
substrates.
Organic Chemistry Frontiers,
Journal Year:
2023,
Volume and Issue:
10(14), P. 3479 - 3484
Published: Jan. 1, 2023
A
visible-light
induced
radical
cyclization
of
olefinic
amides
with
easily
available
N
-sulfonylaminopyridinium
salts
towards
iminoisobenzofurans
and
benzoxazines
has
been
developed.
Advanced Synthesis & Catalysis,
Journal Year:
2024,
Volume and Issue:
366(7), P. 1517 - 1522
Published: Jan. 31, 2024
Abstract
A
photoredox‐catalyzed
three‐component
sulfonaminoformyloxylation
reaction
between
alkenes,
N
‐aminopyridinium
salts
and
DMF
has
been
developed,
which
avoids
the
usage
of
erosive
formic
acid
as
formyloxylation
reagent.
Besides
DMF,
alkyl
aryl
carboxylic
acids
proved
to
be
feasible
nucleophiles
afford
various
β
‐amino
esters.
The
robustness
this
method
was
further
demonstrated
by
its
applicability
in
late‐stage
modification
biological
molecules.
Control
experiments
suggested
that
a
sulfonamidyl
radical
involved
reaction.
Chemical Communications,
Journal Year:
2024,
Volume and Issue:
60(25), P. 3413 - 3416
Published: Jan. 1, 2024
Unsymmetrical
vicinal
diamines
have
been
achieved
via
the
photoredox-catalyzed
difunctionalization
of
alkenes
by
using
N
-aminopyridinium
salts
and
nitriles
as
amination
reagents,
respectively.
The Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
89(1), P. 644 - 655
Published: Dec. 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.
The Journal of Organic Chemistry,
Journal Year:
2025,
Volume and Issue:
unknown
Published: April 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.
Advanced Synthesis & Catalysis,
Journal Year:
2024,
Volume and Issue:
366(9), P. 2003 - 2007
Published: March 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.
European Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
27(19)
Published: March 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.
