Compounds,
Journal Year:
2024,
Volume and Issue:
4(4), P. 626 - 649
Published: Oct. 11, 2024
The
smallest
strained,
saturated
N-heterocycles,
such
as
aziridine,
can
be
a
valuable
building
block
in
synthetic
organic
chemistry.
Ring-opening
reactions
with
various
nucleophiles
could
the
most
important
strategy
to
synthesize
value-added
molecular
entities.
Therefore,
regioselective
ring-opening
of
aziridines
heteroatomic
and
carbon
establish
useful
methodology
biologically
relevant
β-functionalized
alkylamines.
regio-selective
is
highly
dependent
on
substrate
combination,
stereochemical
control
challenging
for
Lewis
acid-promoted
reactions.
development
robust,
catalytic
process
that
assists
accurate
prediction
regioselectivity
stereochemistry
desirable.
Consequently,
large
number
publications
detailing
distinct
methods
aziridine
found
literature.
In
this
review,
we
discuss
several
transition
metal
catalyzed
cross-coupling
reaction
protocols
ring
opening
substituted
nucleophiles.
Organic Chemistry Frontiers,
Journal Year:
2024,
Volume and Issue:
11(14), P. 3974 - 3981
Published: Jan. 1, 2024
A
defluorinative
cyclization
of
readily
available
trifluoromethyl
enones
with
phosphine
oxides
for
the
synthesis
polysubstituted
furans
is
developed
in
a
pure
water
solution.
Organic Letters,
Journal Year:
2025,
Volume and Issue:
unknown
Published: March 10, 2025
The
transition-metal-catalyzed
ring-opening
functionalization
of
aziridines
presents
a
promising
approach
for
synthesizing
structurally
complex
amines.
However,
the
rearranged
poses
significant
challenges.
Herein,
we
report
first
alkenylation
with
aryl
alkenes
via
Ni-Brønsted
acid
co-catalysis,
leading
to
rapid
synthesis
diverse
array
allylamines
yields
reaching
up
91%.
Mechanistic
studies
suggest
that
reaction
occurs
through
rearrangement
aziridine
generate
an
imine
intermediate.
This
intermediate
is
subsequently
captured
by
alkene
under
nickel
catalysis,
ultimately
formation
allylamines.
Organic Letters,
Journal Year:
2023,
Volume and Issue:
25(51), P. 9124 - 9129
Published: Nov. 17, 2023
Herein,
we
describe
a
novel
and
efficient
photoredox
catalytic
Cα
radical
addition/defluoroalkylation
coupling
reaction
between
α-trifluoromethyl
alkenes
N-trifluoroethyl
hydroxylamine.
A
series
of
gem-difluoroallylated
α-trifluoromethylamines
were
synthesized
by
the
addition
enabled
1,2-H
shift
in
situ-generated
radical.
Notably,
this
protocol
is
distinguished
its
mild
conditions,
easy
operation,
excellent
functional
group
tolerability.
Green Chemistry,
Journal Year:
2024,
Volume and Issue:
26(17), P. 9371 - 9377
Published: Jan. 1, 2024
Defluorinative
alkylation
and
arylation
between
thianthrenium
salts
α-trifluoromethyl
alkene
to
afford
gem
-difluoroolefins
by
easily
recycling
thianthrene
under
visible
light
irradiation
free
of
metal
photocatalyst.
The Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
89(5), P. 3251 - 3258
Published: Feb. 15, 2024
Aziridines
are
important
structural
motifs
and
intermediates,
several
synthetic
strategies
for
the
direct
aziridination
of
alkenes
have
been
introduced.
However,
many
these
require
an
excess
activated
alkene,
suffer
from
competing
side-reactions,
limited
functional
group
tolerance,
or
involve
precious
transition
metal-based
catalysts.
Herein,
we
demonstrate
by
combining
sulfonyl
azides
as
a
triplet
nitrene
source
with
catalytic
amount
organic
dye
functioning
photosensitizer.
We
show
how
nature
azide,
in
combination
triplet-excited
state
energy
photosensitizer,
affects
yield
provide
mechanistic
rationale
to
account
observed
dependence
reaction
on
azide
reagents.
The
optimized
conditions
enable
structurally
diverse
complex
alkenes,
carrying
various
groups,
alkene
limiting
reagent.
Organic Chemistry Frontiers,
Journal Year:
2024,
Volume and Issue:
11(18), P. 5144 - 5150
Published: Jan. 1, 2024
A
transition-metal-free
multi-functionalization
reaction
of
β-trifluoromethyl
enones
and
azacycles
is
first
developed
for
the
synthesis
valuable
amino-2,3-dihydrofuran
derivatives.
Organic Letters,
Journal Year:
2024,
Volume and Issue:
unknown
Published: Sept. 12, 2024
An
efficient
approach
for
the
remote
C-H
alkylation
of
arenes,
employing
a
variety
N-directing
groups
is
described.
This
method
facilitates
straightforward
synthesis
valuable
phenylethylamine
derivatives
by
exclusively
cleaving
benzylic
C-N
bond
in
aziridines.
Furthermore,
these
products
can
easily
remove
protecting
groups,
resulting
meta-substituted
compounds,
such
as
amines
and
ketones,
which
hold
significance
synthetic
chemistry.
Organic Letters,
Journal Year:
2025,
Volume and Issue:
unknown
Published: Jan. 8, 2025
A
remarkably
simple
and
efficient
double
defluorinative
[3
+
3]
annulation
approach
involving
N-phenyl-α-fluoro-α-phenylsulfonylacetamide
2-CF3-alkenes
to
access
N-phenyl-3,6-difluoropyridone
derivatives
has
been
achieved.
The
key
the
success
of
this
single-step
synthesis
difluoropyridones
is
strategic
utilization
for
consecutive
allylic
vinylic
substitution
reactions
a
desulfonylation
cascade.
We
could
also
show
that
these
serve
as
versatile
platform
C-6-selective
functionalizations.
