Cyano
groups
represent
an
important
class
of
functional
motifs
in
medicinal
chemistry
given
their
synthetic
versatility
and
capacity
to
engage
essential
interactions
with
biological
targets.
However,
the
synthesis
sterically
hindered
alkyl
nitriles
using
non-toxic
reagents
remains
challenging.
Traditional
methods
often
rely
on
toxic
cyanide
sources
suffer
from
limited
substrate
scope.
Herein,
we
report
a
photoredox
catalyzed,
metal-free
deoxycyanation
alcohols
that
allows
rapid
access
wide
array
1º,
2º,
3º
cyanides
reagents.
Organic Letters,
Год журнала:
2024,
Номер
26(18), С. 3977 - 3981
Опубликована: Апрель 29, 2024
A
denitrative
cyanation
of
nitroarenes
using
organocyanides
and
a
palladium
catalyst
was
developed.
The
key
for
this
reaction
the
utilization
an
aminoacetonitrile
as
cyano
source
to
avoid
generation
stoichiometric
metal-
halogen-containing
chemical
waste.
wide
range
nitroarenes,
including
heteroarenes
pharmaceutical
molecules,
can
be
converted
into
aryl
nitriles.
Angewandte Chemie International Edition,
Год журнала:
2024,
Номер
63(47)
Опубликована: Авг. 12, 2024
Abstract
Herein,
we
disclose
the
first
report
on
gold‐catalyzed
C(sp
2
)‐CN
cross‐coupling
reaction
by
employing
a
ligand‐enabled
Au(I)/Au(III)
redox
catalysis.
This
transformation
utilizes
acetone
cyanohydrin
as
nucleophilic
cyanide
source
to
convert
simple
aryl
and
alkenyl
iodides
into
corresponding
nitriles.
Combined
experimental
computational
studies
highlighted
crucial
role
of
cationic
silver
salts
in
activating
stable
(P,N)‐AuCN
complex
towards
oxidative
addition
subsequently
generate
key
aryl‐Au(III)
complexes.
Chemical Communications,
Год журнала:
2025,
Номер
unknown
Опубликована: Янв. 1, 2025
A
silver-catalyzed
cross
coupling
of
cyclic
aldimines
and
α-imino-oxy
acids
has
been
developed.
The
solvent-dependent
reaction
could
selectively
deliver
either
imine
moiety
retained
nitriles
or
ring-opened
oxonitriles
in
moderate
yields.
Chemical Science,
Год журнала:
2024,
Номер
15(32), С. 12989 - 13000
Опубликована: Янв. 1, 2024
A
harmonious
axial-coordinated
Pt
x
Fe/FeN
4
CCl
catalyst
was
designed
and
fabricated
by
a
simple
method,
integrating
structurally
ordered
PtFe
intermetallic
with
an
orbital
electron-delocalization
FeN4CCl
support
for
synergistic
ORR
catalysis.
European Journal of Organic Chemistry,
Год журнала:
2024,
Номер
27(45)
Опубликована: Авг. 27, 2024
Abstract
Nitroarenes
are
fundamental
feedstocks
in
the
chemical
industry.
Their
relatively
inert
C−NO
2
bond
allows
for
late‐stage
modifications
of
molecules
and
exhibits
complete
orthogonality
to
reactivity
C‐halogen
cross‐coupling
reactions.
The
denitrative
functionalization
nitroarenes
holds
significant
appeal
due
it
avoids
use
aryl
halides,
thereby
simplifying
reaction
steps
improving
atom
step
economy.
Recent
progress
direct
includes
palladium‐catalyzed
coupling,
copper‐catalyzed
as
well
metal‐free
one‐pot
functionalization.
In
this
review,
we
provide
a
concise
overview
these
advancements,
detailing
features
mechanisms.
This
summary
aims
highlight
versatility
efficiency
methodologies,
offering
insights
into
their
potential
applications
inspiring
further
research
promising
area
organic
synthesis.
Organic Letters,
Год журнала:
2024,
Номер
26(9), С. 1908 - 1913
Опубликована: Фев. 26, 2024
An
intermolecular
controllable
Pd-catalyzed
spirocyclization
of
isocyano
cycloalkenes
has
been
developed,
offering
efficient
and
selective
approaches
toward
spirocyclic
hydropyrrole
scaffolds.
2-Azaspiro-1,7-dienes
could
be
obtained
through
a
"chain-walking"
process
with
aryl/vinyl
iodides
as
electrophiles,
while
the
normal
Heck
product
2-azaspiro-1,6-dienes
were
selectively
generated
when
aryl
triflates
used
coupling
partner
isocyanides.
Mechanistic
studies
suggested
that
counteranion
Pd(II)
intermediate
played
crucial
role
in
regioselectivity
control.
Dihydropyrrole-fused
5,6,7-membered
spirocycles
switchably
accessed
under
mild
conditions
wide
functional
group
tolerance.
Asian Journal of Organic Chemistry,
Год журнала:
2024,
Номер
13(11)
Опубликована: Июль 22, 2024
Abstract
Thiourea
dioxide
(TDO)
has
been
demonstrated
to
be
an
efficient
reagent
for
the
transformation
of
aromatic,
heteroaromatic,
alkenyl
and
aliphatic
aldoximes
respective
nitriles
in
excellent
yields.
Furthermore,
this
method
applied
synthesis
fungicide
cyazofamid
from
a
commercial
precursor
using
TDO
as
pivotal
dehydrating
reducing
reagent.
This
new
procedure
offers
simple
easily
reproducible
technique
nitrile
highlights
synthetic
utility
versatile
organic
chemistry.
Chemical Science,
Год журнала:
2024,
Номер
15(35), С. 14188 - 14194
Опубликована: Янв. 1, 2024
A
photoredox
catalytic
strategy
has
been
developed
to
enable
the
functionalization
of
a
variety
commercially
available,
structurally
different
radical
precursors
by
use
bench-stable
isonitrile
as
an
efficient
cyanating
reagent.
Specifically,
radical-based
reaction
provided
mild
and
convenient
procedure
for
cyanation
primary,
secondary
tertiary
radicals
derived
from
widely
accessible
sp
Letters in Organic Chemistry,
Год журнала:
2024,
Номер
22(1), С. 70 - 77
Опубликована: Май 30, 2024
The
synthesis
of
α,β-unsaturated
compounds
is
crucial
in
organic
chemistry,
especially
drug
discovery
and
pharmaceutical
development.
In
this
study,
NCP@POCl<sub>2</sub>-x
(Fe<sub>3</sub>O<sub>4</sub>@SiO<sub>2</sub>@
chitosan@POCl<sub>2</sub>-x)
has
been
introduced
as
a
new,
environmentally
friendly,
highly
efficient
heterogeneous
magnetic
nanocatalyst
for
the
carboxylic
acids.
This
catalyst
facilitates
<i>in
situ</i>
transformation
POCl<sub>2</sub>-x
to
PO(OH)<sub>2</sub>
presence
water,
effectively
converting
β-hydroxy
nitriles
into
acids
through
specific
mechanism
involving
water
heat.
reactions
display
notable
regioselectivity,
leading
high-purity
products
quantitative
yields.
NCP@PO(OH)<sub>2</sub>
exhibits
heterogeneity,
properties,
straightforward
recovery,
outstanding
performance,
making
it
valuable
selective
transformations
nitriles.
Additionally,
can
be
easily
separated
from
mixture
using
external
forces.
Angewandte Chemie,
Год журнала:
2024,
Номер
136(47)
Опубликована: Авг. 12, 2024
Abstract
Herein,
we
disclose
the
first
report
on
gold‐catalyzed
C(sp
2
)‐CN
cross‐coupling
reaction
by
employing
a
ligand‐enabled
Au(I)/Au(III)
redox
catalysis.
This
transformation
utilizes
acetone
cyanohydrin
as
nucleophilic
cyanide
source
to
convert
simple
aryl
and
alkenyl
iodides
into
corresponding
nitriles.
Combined
experimental
computational
studies
highlighted
crucial
role
of
cationic
silver
salts
in
activating
stable
(P,N)‐AuCN
complex
towards
oxidative
addition
subsequently
generate
key
aryl‐Au(III)
complexes.
