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.
Journal of the American Chemical Society,
Год журнала:
2024,
Номер
146(4), С. 2845 - 2854
Опубликована: Янв. 18, 2024
In
this
report,
we
developed
a
unified
and
standardized
one-pot
sequence
that
converts
pyridine
derivatives
into
1,2-diazepines
by
inserting
nitrogen
atom.
This
skeletal
transformation
capitalizes
on
the
in
situ
generation
of
1-aminopyridinium
ylides,
which
rearrange
under
UV
light
irradiation.
A
thorough
evaluation
key
parameters
(wavelength,
reaction
conditions,
activating
agent)
allowed
us
to
elaborate
simple,
mild,
user-friendly
protocol.
The
model
was
extrapolated
more
than
40
examples,
including
drug
derivatives,
affording
unique
7-membered
structures.
Mechanistic
evidence
supports
transient
presence
diazanorcaradiene
species.
Finally,
pertinent
transformations
products,
ring
contraction
reactions
form
pyrazoles,
were
conducted
paved
way
broad
application
Angewandte Chemie International Edition,
Год журнала:
2023,
Номер
62(30)
Опубликована: Май 26, 2023
Abstract
N
‐(difluoromethyl)amino
(−NCF
2
H)
compounds
are
of
great
interest
given
their
unique
and
underexplored
physiochemical
properties.
The
lack
structural
diversity
in
NCF
H
is
likely
due
part
to
the
shortage
protocols
for
efficient
installation.
Presented
herein
a
new
shelf‐stable
pyridinium
reagent
that
enables
direct
installation
‐(difluoromethyl)sulfonamide
moiety
[N(Ts)CF
H)]
onto
(hetero)arenes
alkenes
diversification
aryl
alkyl
compounds.
described
protocol
utilizes
blue
light
photoredox
catalysis
displays
broad
functional
group
tolerance
with
excellent
chemoselectivity.
Additional
transformations
applicability
towards
continuous
flow
also
demonstrated.
Organic Chemistry Frontiers,
Год журнала:
2023,
Номер
10(14), С. 3479 - 3484
Опубликована: Янв. 1, 2023
A
visible-light
induced
radical
cyclization
of
olefinic
amides
with
easily
available
N
-sulfonylaminopyridinium
salts
towards
iminoisobenzofurans
and
benzoxazines
has
been
developed.
Chemical Communications,
Год журнала:
2024,
Номер
60(25), С. 3413 - 3416
Опубликована: Янв. 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.
Organic Letters,
Год журнала:
2023,
Номер
25(38), С. 7009 - 7013
Опубликована: Сен. 14, 2023
The
1,2-iminylalkylation
of
diazenes
using
alkyl
iodides
in
combination
with
an
O-benzoyl
oxime
is
reported.
In
this
transformation,
acted
as
a
radical
precursor
and
XAT
mediator.
addition
to
common
iodides,
other
such
iodomethane,
iodomethane-d3,
trifluoroiodomethane,
ethyl
difluoroiodoacetate,
iodoalkanes
containing
unprotected
hydroxyl
amide
groups
can
also
serve
C-radical
precursors
the
electrophilic
acceptors.
Advanced Synthesis & Catalysis,
Год журнала:
2024,
Номер
366(7), С. 1517 - 1522
Опубликована: Янв. 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.