European Journal of Organic Chemistry,
Год журнала:
2024,
Номер
unknown
Опубликована: Дек. 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.
The Journal of Organic Chemistry,
Год журнала:
2023,
Номер
88(17), С. 12630 - 12640
Опубликована: Авг. 14, 2023
We
report
a
new
method
for
the
synthesis
of
trifluoromethylated
and
sulfonylated
oxazolines
by
electrochemical
radical
cascade
cyclizations
N-allylamides
with
sodium
trifluoromethanesulfinate
or
sulfonylhydrazines.
This
protocol
provides
green
useful
strategy
to
synthesize
broad
substrate
scope
under
ambient
conditions.
Chinese Journal of Chemistry,
Год журнала:
2024,
Номер
42(18), С. 2235 - 2242
Опубликована: Май 11, 2024
Comprehensive
Summary
A
visible‐light‐induced
photoredox‐catalyzed
regioselective
and
stereoselective
C(sp
2
)–H
amination
of
enamides
with
bench‐stable
easily
accessible
N
‐aminopyridium
salts
is
developed,
affording
synthetically
biologically
prominent
vicinal
1,2‐diamine
scaffolds
broad
substrate
scope
excellent
functional
group
compatibility.
The
transformation
proceeded
through
a
radical
pathway
involving
the
Giese
addition
relatively
electrophilic
‐centered
sulfonamidyl
species
to
nucleophilic
β‐olefinic
position
followed
by
ensuing
single
electron
oxidation
β‐H
elimination,
delivering
geometrically‐defined
Z
‐configured
β‐sulfonamidylated
enamides.
operational
simplicity,
environmental
friendliness
cost
efficiency
this
methodology
allowed
it
pave
new
avenue
enrich
arsenal
crucial
functionalized
their
related
derivatives.
Organic Chemistry Frontiers,
Год журнала:
2024,
Номер
11(20), С. 5784 - 5790
Опубликована: Янв. 1, 2024
The
radical
cascade
cyclization
of
vinyl-tethered
alkenes
has
become
a
promising
tool
for
rapidly
assembling
nonbenzene-fused
cyclic
skeletons
via
the
cracking
alkenyl
C–H
bonds,
but
this
approach
been
limited
to
generate
five-membered
rings.
Asian Journal of Organic Chemistry,
Год журнала:
2023,
Номер
12(8)
Опубликована: Июль 8, 2023
Abstract
Sulfonamide
is
one
of
the
most
important
structures
in
organic
chemistry
due
to
its
frequent
appearance
natural
products
as
well
pharmaceuticals.
This
study
reports
a
visible‐light‐promoted
strategy
for
synthesis
sulfonamides
from
arylazo
sulfones.
One‐pot
tri‐component
reactions
were
conducted
using
sulfones,
DABSO,
and
amines
presence
CuBr
2
coupling
catalyst
under
irradiation
with
blue
LEDs
prepare
various
good
yields
mild
conditions.
method
could
be
used
effectively
produce
variety
useful
sulfonamides.
Chemical Communications,
Год журнала:
2023,
Номер
59(67), С. 10125 - 10128
Опубликована: Янв. 1, 2023
Reported
herein
is
the
design
and
development
of
a
new
photo-induced
amidation
protocol
with
readily
available
N-chlorosulfonyl
carbamate
as
an
effective
amidyl-radical
precursor,
which
could
be
prepared
from
commercial
low-cost
chlorosulfonyl
isocyanate
(CSI)
alcohol
feedstocks.
The
synthetic
potency
this
developed
was
well
demonstrated
by
direct
various
quinoxalin-2(1H)-ones.
further
streamlined
implementing
one-pot/two-step/three-component
process
CSI,
alcohol,
quinoxalin-2(1H)-one,
significantly
improved
reaction
efficiency.
This
methodology
offers
intriguing
opportunity
for
rapid
expansion
nitrogen-containing
molecular
complexity,
thus
inspiring
comprehensive
exploration
mode
CSI
reagent.
European Journal of Organic Chemistry,
Год журнала:
2023,
Номер
26(46)
Опубликована: Окт. 30, 2023
Abstract
Photo‐induced
sulfonylamidation/lactonization
of
alkenyl
acids
with
N
‐sulfonylaminopyridinium
salts
is
demonstrated
to
access
sulfonamidylated
lactones
under
mild
and
metal‐free
conditions.
This
reaction
features
a
broad
substrate
scope,
good
functional
group
tolerance
easy
operation,
providing
simple
efficient
protocol
for
the
synthesis
lactones.
Chinese Journal of Chemistry,
Год журнала:
2024,
Номер
unknown
Опубликована: Сен. 10, 2024
Comprehensive
Summary
Two
reaction
modes
for
metal‐free
[3
+
2]
cyclization
of
N
‐aminopyridinium
derivatives
with
β
‐alkoxyvinyl
trifluoromethylketones
have
been
described
through
selective
C—O
or
C—O/C—C
bond
cleavage.
This
strategy
can
also
be
extended
to
the
enaminones
and
bromoalkynes.
A
broad
range
‐aminopyridinium,
‐aminoquinolinium,
‐aminoisoquinolinium
salts
are
well
tolerated,
enabling
divergent
synthesis
trifluoroacylated,
non‐substituted,
acylated,
brominated
pyrazolo[1,5‐
a
]pyridine
(62
examples).
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
unknown
Опубликована: Дек. 26, 2024
A
photoredox-catalyzed
aminolactonization
of
unsaturated
carboxylic
acids
was
achieved
using
N-aminopyridinium
salts
as
the
amino
radical
precursor.
The
transformation
features
mild
conditions
and
a
remarkably
broad
substrate
scope,
offering
an
efficient
approach
to
construct
wide
range
4-sulfonamino
3,4-dihydroisocoumarins.
Mechanistic
studies
indicate
that
reaction
proceeds
via
distinctive
salt-promoted
electrophilic
amination
2-styrylbenzoic
acids.
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(9), С. 6465 - 6473
Опубликована: Апрель 22, 2024
An
electrochemical
protocol
for
benzylic
C(sp3)–H
aminopyridylation
via
direct
C–H/N–H
cross-coupling
of
alkylarenes
with
N-aminopyridinium
triflate
has
been
developed.
This
method
features
excellent
site-selectivity,
broad
substrate
scope,
redox
reagent-free
and
facile
scalability.
The
generated
benzylaminopyridiniums
can
be
readily
converted
to
benzylamines
electroreductive
N–N
bond
cleavage.
New Journal of Chemistry,
Год журнала:
2023,
Номер
47(26), С. 12487 - 12491
Опубликована: Янв. 1, 2023
A
facile
and
practical
silver-mediated
radical
cascade
cyclization
of
N
-allylamides
with
sodium
sulfinates
is
developed,
giving
a
series
sulfonated
oxazolines
in
moderate
to
good
yields.
