The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(12), С. 8656 - 8667
Опубликована: Июнь 4, 2024
The
nucleophilic
ring-opening
of
aziridine
derivatives
provides
an
important
synthetic
tool
for
the
preparation
various
β-functionalized
amines.
Amines
as
nucleophiles
are
employed
to
prepare
synthetically
useful
1,2-diamines
in
presence
catalysts
or
activators.
Herein,
B2(OH)4-mediated
reductive
transformation
N-tosyl
aziridines
by
nitroarenes
was
developed.
This
aqueous
protocol
cheap
and
readily
available
amino
sources
proceeds
under
external
catalyst-free
conditions.
Control
experiments
DFT
calculations
pointed
situ
reduction
aryl
amines
via
N-aryl
boramidic
acid
(E)
SN1-type
N-tosylaziridines
resultant
with
high
regioselectivity.
Organic Chemistry Frontiers,
Год журнала:
2024,
Номер
11(9), С. 2638 - 2664
Опубликована: Янв. 1, 2024
This
review
describes
the
recent
advances
in
different
reaction
types
and
catalytic
systems
for
construction
of
C–NAr
S–NAr
bonds
by
nitroaromatic
reductive
cross-coupling.
European Journal of Organic Chemistry,
Год журнала:
2024,
Номер
27(18)
Опубликована: Март 16, 2024
Abstract
We
report
the
efficient,
sustainable
one‐pot
synthesis
of
a
wide
variety
N
‐polyheterocycles,
such
as
imidazo‐quinolines
and
quinoxalines,
furoquinolines,
from
easily
available
nitroaromatics
glycols
via
molybdenum
catalytic
domino
reduction‐imine
formation‐intramolecular
cyclization‐oxidation
sequence.
It
is
worth
highlighting
that
recycling
incorporation
waste
carbonyl
byproduct,
generated
in
reduction
step,
into
final
compound
realized.
In
addition,
overall
efficiency
atom
economy
process
are
further
improved
owing
to
participation
one
reaction
intermediate
reductant
allows
lowering
amount
external
reducing
agent
employed.
We
have
realized
a
cathodic
deoxygenative
alkylation
between
nitro(hetero)arenes
and
organic
halides,
employing
bis(pinacolato)diboron
(B2pin2)
LiCl
as
additives
to
trap
stabilize
the
generated
alkyl
radicals
carbanions,
thereby
facilitating
efficient
N-O
cleavage
selective
C-N
bond
formation.
The
protocol
offers
an
economical
method
for
synthesis
of
multiple
aromatic(hetero)
amines,
without
need
reactive
reductants
exclusion
air
moisture.
Notably,
is
distinguished
by
scalability,
broad
functional
group
compatibility,
safe
mild
conditions,
demonstrating
practicality
in
late-stage
modification
various
bioactive
compounds.
Aryl
iodides
are
essential
synthons
in
organic
synthesis,
whose
conventional
preparations
often
suffer
from
poor
selectivity
or
necessitate
multistep
procedures.
Herein,
we
present
a
light-driven
denitrative
iodination
as
one-step
approach
that
directly
converts
nitroarenes
to
iodoarenes
under
mild
and
transition-metal-free
conditions.
This
streamlined
method
operates
the
absence
of
strong
Brønsted
acids,
ensuring
broad
functional
group
tolerance,
including
esters,
cyano
groups,
halides,
heterocycles,
while
also
offering
operational
simplicity
scalability.
Abstract
A
new
mild
and
chemoselective
method
for
the
preparation
of
various
aminoarenes
is
described,
based
on
electrochemical
catalytic
reduction
nitroaryl
derivatives
promoted
by
samarium
salts
in
methanol.
The
reactions
are
carried
out
air,
an
undivided
cell,
at
room
temperature
tolerate
a
wide
range
functional
groups,
including
some
reducible
ones,
without
leading
to
by‐products.
This
procedure
also
effective
complete
challenging
substrates,
namely
those
capable
coordinating
metals,
traditionally
need
drastic
conditions
terms
pressure,
reaction
time
or
temperature.
47
examples
one
nitroalkane,
all
lead
targeted
reduced
product
yields
that
almost
always
over
90
%.
Organic Chemistry Frontiers,
Год журнала:
2024,
Номер
unknown
Опубликована: Ноя. 14, 2024
We
report
a
visible
light-mediated
[1
+
2
2]
cycloaddition
reaction
between
nitroarenes
and
alkenes,
conducted
under
mild
conditions,
to
synthesize
isoxazolidines.
