Compounds,
Год журнала:
2024,
Номер
4(4), С. 626 - 649
Опубликована: Окт. 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.
Advanced Synthesis & Catalysis,
Год журнала:
2024,
Номер
366(10), С. 2246 - 2251
Опубликована: Март 29, 2024
Abstract
Herein,
a
visible
light‐mediated
defluorination
reaction
to
access
1,1‐difluoro‐1,3‐enynes
is
described.
Compared
with
previous
studies,
this
protocol
employs
more
readily
accessible
acids
as
radical
precursor
under
redox‐neutral
conditions.
Moreover,
the
exhibits
high
compatibility
diverse
primary,
secondary
and
tertiary
acids,
especially
natural
amino
drug‐derived
acids.
Preliminary
mechanistic
investigations
reveal
that
pathway
involved
in
catalytic
cycle.
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(12), С. 8342 - 8356
Опубликована: Май 31, 2024
A
mild
and
transition-metal-free
defluorinative
alkylation
of
benzyl
amines
with
trifluoromethyl
alkenes
is
reported.
The
features
this
protocol
are
easy-to-obtain
starting
materials,
a
wide
range
substrates,
functional
group
tolerance
as
well
high
atom
economy,
thus
offering
strategy
to
access
variety
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(16), С. 11429 - 11445
Опубликована: Авг. 1, 2024
A
transition
metal-free,
atom-economical,
and
highly
stereospecific
synthetic
approach
to
Friedel–Crafts-type
alkylation
of
arenes/heteroarenes
has
been
developed.
The
protocol
involves
the
catalytic
aminium
radical-cation
salt
(Magic
Blue)-initiated
SN2-type
nucleophilic
ring
opening
activated
aziridines
with
give
corresponding
2,2-diarylethylamines
up
99%
yield
85%
ee
(for
nonracemic
aziridines)
in
a
very
short
reaction
time.
Moreover,
on
1,3-dimethylindole
benzofuran,
undergo
domino-ring-opening
cyclization
(DROC)
various
biologically
significant
heterocyclic
scaffolds
moderate
good
yields.
Abstract
Aziridines,
which
serve
as
valuable
scaffolds
in
numerous
pharmaceuticals
and
bioactive
molecules,
have
emerged
highly
efficient
C(sp3)
precursors
the
realm
of
organic
chemistry.
Particularly,
employing
aziridines
versatile
electrophiles
transition-metal-catalyzed
cross-coupling
has
enabled
precise
control
over
regiochemistry
formation
new
C(sp3)–C,
–Si,
–B
bonds.
This
review
explores
recent
innovative
aziridine
approaches
using
Ni
or
Pd
catalysis,
highlighting
initial
findings
mechanistic
delineating
distinct
catalytic
pathways.
1
Introduction
2
Aziridines
Used
Precursors
with
Organometallic
Reagents
2.1
Ni-Catalyzed
Aziridine
Cross-Coupling
2.2
Pd-Catalyzed
3
Net-Reductive
Approaches
via
Cross-Electrophile
Coupling
3.1
Using
Chemical
Reductants
3.2
Electrochemical
Reductions
4
Metallaphotoredox
Catalysis
4.1
Metallaphotoredox-Catalyzed
4.2
Redox-Neutral
5
Miscellaneous
6
Conclusion
Future
Outlook
Abstract
N-(Difluoropropenyl)amides/amines
are
an
important
class
of
fluorinated
compounds.
Here,
we
report
efficient
method
for
synthesizing
these
compounds
without
the
use
transition
metals.
Under
simple
base-promoted
conditions,
3-bromo-3,3-difluoroprop-1-ene
reacts
with
N-methylanilines
or
N-arylacrylamides,
elimination
one
molecule
HBr,
to
give
target
compound.
Another
difluoroalkenes
is
reaction
2-bromo-3,3,3-trifluoroprop-1-ene
indole
its
analogues.
Compounds,
Год журнала:
2024,
Номер
4(4), С. 626 - 649
Опубликована: Окт. 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.
