Angewandte Chemie International Edition,
Journal Year:
2022,
Volume and Issue:
62(9)
Published: Dec. 21, 2022
β-Arylethylamines
are
prevalent
structural
motifs
in
molecules
exhibiting
biological
activity.
Here
we
report
a
sequential
one-pot
protocol
for
the
1,2-aminoarylation
of
alkenes
with
hydroxylammonium
triflate
salts
and
(hetero)arenes.
Unlike
existing
methods,
this
reaction
provides
direct
entry
to
unprotected
β-arylethylamines
remarkable
functional
group
tolerance,
allowing
key
drug-oriented
groups
be
installed
two-step
process.
The
use
hexafluoroisopropanol
as
solvent
combination
an
iron(II)
catalyst
proved
essential
reaching
high-value
nitrogen-containing
molecules.
Chemistry - An Asian Journal,
Journal Year:
2022,
Volume and Issue:
17(12)
Published: April 23, 2022
Alkene
amino(hetero)arylation
presents
a
highly
efficient
and
straightforward
strategy
for
direct
installation
of
amino
groups
heteroaryl
rings
across
double
bond
simultaneously.
An
extensive
array
practical
transformations
has
been
developed
via
alkene
difunctionalization
approach
to
access
broad
range
medicinally
valuable
(hetero)arylethylamine
motifs.
This
review
recent
progress
in
1,2-amino(hetero)arylation
alkenes
organized
three
different
modes.
First,
intramolecular
employing
C,
N-tethered
will
be
introduced.
Next,
two-component
reactions
discussed
with
combination
precursors,
external
aryl
precursor,
C-tethered
amine
or
reagents,
alkenes.
Last,
three-component
intermolecular
covered.
Organic Letters,
Journal Year:
2023,
Volume and Issue:
25(22), P. 4113 - 4118
Published: May 30, 2023
A
photoredox-catalyzed
1,2-amidoheteroarylation
of
unactivated
alkenes
with
O-acyl
hydroxylamine
derivatives
and
heterocycles
is
presented.
range
heterocycles,
including
quinoxaline-2(1H)-ones,
azauracils,
chromones,
quinolones,
are
capable
for
this
process,
allowing
the
direct
synthesis
valuable
heteroarylethylamine
derivatives.
Structurally
diverse
reaction
substrates,
drug-based
scaffolds,
were
successfully
applied,
demonstrating
practicality
method.
Angewandte Chemie International Edition,
Journal Year:
2021,
Volume and Issue:
60(37), P. 20215 - 20219
Published: June 21, 2021
Radical-mediated
difunctionalization
of
alkenes
provides
a
promising
approach
to
introduce
one
alkenyl
or
alkynyl
group
target
compounds.
However,
simultaneous
installation
two
unsaturated
C-C
bonds
via
alkene
remains
elusive,
attributable
the
high
instability
and
transient
lifetimes
radicals.
Herein,
we
report
photocatalytic
1,2-alkynylalkenylation
1,2-enynylalkenylation
for
first
time,
triggered
by
intermolecular
addition
stabilized
allenyl
radical
an
alkene.
A
portfolio
strategically
designed,
easily
accessible
dual-function
reagents
are
applied
docking-migration
cascade.
The
protocol
has
broad
substrate
scope
efficiently
increases
degree
unsaturation.
Chemical Science,
Journal Year:
2022,
Volume and Issue:
13(23), P. 6942 - 6949
Published: Jan. 1, 2022
Arylethylamines
are
abundant
motifs
in
myriad
natural
products
and
pharmaceuticals,
so
efficient
methods
to
synthesize
them
valuable
drug
discovery.
In
this
work,
we
disclose
an
intramolecular
alkene
aminoarylation
cascade
that
exploits
the
electrophilicity
of
a
nitrogen-centered
radical
form
C-N
bond,
then
repurposes
nitrogen
atom's
sulfonyl
activating
group
as
traceless
linker
subsequent
C-C
bond.
This
photoredox
catalysis
protocol
enables
preparation
densely
substituted
arylethylamines
from
commercially
aryl
sulfonamides
unactivated
alkenes
under
mild
conditions.
Reaction
optimization,
scope,
mechanism,
synthetic
applications
discussed.
Angewandte Chemie International Edition,
Journal Year:
2022,
Volume and Issue:
62(9)
Published: Dec. 21, 2022
β-Arylethylamines
are
prevalent
structural
motifs
in
molecules
exhibiting
biological
activity.
Here
we
report
a
sequential
one-pot
protocol
for
the
1,2-aminoarylation
of
alkenes
with
hydroxylammonium
triflate
salts
and
(hetero)arenes.
Unlike
existing
methods,
this
reaction
provides
direct
entry
to
unprotected
β-arylethylamines
remarkable
functional
group
tolerance,
allowing
key
drug-oriented
groups
be
installed
two-step
process.
The
use
hexafluoroisopropanol
as
solvent
combination
an
iron(II)
catalyst
proved
essential
reaching
high-value
nitrogen-containing
molecules.
