The Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
89(4), P. 2571 - 2581
Published: Feb. 7, 2024
The
catalytic
intermolecular
arylation
of
disubstituted
geminal
dinitriles
with
in
situ
generated
arylnickel
complexes
is
disclosed.
This
method
efficiently
provides
various
all-carbon
substituted
α-cyanocarbonyl
compounds
without
additives
and
an
inert
atmosphere.
It
also
demonstrates
the
R-BINOL
S-BINOL
derived
dinitriles,
preserving
optical
purity.
Mechanistic
studies
proved
that
organonickel
complex
involved
arylation.
Advanced Synthesis & Catalysis,
Journal Year:
2024,
Volume and Issue:
366(6), P. 1220 - 1268
Published: Jan. 22, 2024
Abstract
Elaborated
molecular
architectures,
specifically
those
bearing
one
or
more
carbon
stereocenters,
stand
as
an
important
class
of
carbocyclic
and
heterocyclic
frameworks
because
they
are
frequently
occurring
core
structures
in
numerous
natural
products
biologically
active
pharmaceutical
molecules.
Over
the
past
few
decades,
development
versatile
synthetic
approaches
via
cascade
cyclization
reactions
1,6‐enynes
for
construction
a
series
fused
spiro
compounds
has
been
focus
great
deal
research
initiatives.
These
synthesis
strategies
peculiarly
fascinating
context
assembly
wide
array
molecules,
products,
agrochemicals,
functional
materials.
In
this
review,
recent
developments
transformations
with
diverse
coupling
reagents
summarized
since
2018,
which
could
be
divided
into
five
categories:
1)
Introduction;
2)
Transition
metal
catalyzed
1,6‐enynes;
3)
Metal‐free
4)
Visible‐light‐induced
5)
Electrocatalytic
1,6‐enynes.
Chemistry - An Asian Journal,
Journal Year:
2022,
Volume and Issue:
17(21)
Published: Sept. 1, 2022
In
the
arena
of
functional
group-oriented
organic
synthesis,
nitrile
or
cyano
functionality
is
immense
importance.
The
presence
nucleophilic
N-atom,
π-coordinating
ability
triple
bond,
and
electrophilic
C-center
imparts
unique
interesting
reactivities.
Owing
to
transform
into
various
other
groups
intermediates,
chemistry
very
rich
diverse.
particular,
involvement
in
numerous
reactions
such
as
inter-
intramolecular
alkyne
insertion,
[2+2+2]
cycloaddition
with
alkynes,
[3+2]
azides,
[4+2]
dienes
allow
synthesis
many
important
carbo-
heterocycles.
Furthermore,
serves
a
directing
group
C-H
bond
functionalization
introduce
diverse
functionalities
participate
radical
acceptor
cascade
strategies
obtain
large
variety
molecules.
This
review
mainly
focuses
on
reactivity
synthetic
application
including
functionalization,
cycloaddition,
thermal
photochemical
strategy.
objective
current
aims
at
bringing
out
striking
collection
nitrile-triggered
transformations.
Advanced Synthesis & Catalysis,
Journal Year:
2023,
Volume and Issue:
365(13), P. 2058 - 2091
Published: May 17, 2023
Abstract
Decyanation
is
an
important
process
in
the
synthesis
of
aromatic
molecules
studies
pharmaceutical
research,
medical
and
materials
sciences.
In
late‐stage
modifications
privileged
carbo/heterocyclic
scaffolds,
radical‐type
decyanation
techniques
have
been
devised
to
date.
As
a
result,
chemistry
cyano‐involved
conversions,
hotly
debated
subject
over
past
few
decades,
has
advanced
significantly.
The
cyano
group
(CN),
on
other
hand,
rarely
acknowledged
as
good
reaction
site
due
its
thermodynamic
robustness.
most
recent
advancements
catalytic
radical
protocols
that
CN
behaved
leaving
made
are
surveyed
this
article.
Following
introduction
number
different
modes,
reactions
used
activate
C−CN
bonds
primarily
categorized,
text
herein
divided
into
three
groups:
(1)
photo‐catalyzed
transformations,
(2)
electro‐catalyzed
(3)
transition‐metal‐catalyzed
or
metal‐free
transformations.
With
emphasis
systems
synthetic
applications
bond
activation,
review
will
provide
readers
with
overview
reactions.
Chemical Communications,
Journal Year:
2025,
Volume and Issue:
unknown
Published: Jan. 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 Communications,
Journal Year:
2023,
Volume and Issue:
59(51), P. 7990 - 7993
Published: Jan. 1, 2023
A
visible/solar-light-induced
electron-donor-acceptor
(EDA)-aggregated/mediated
radical
cyclization
between
(E)-2-(1,3-diarylallylidene)malononitriles
and
thiophenols
leads
to
poly-functionalized
pyridines.
The
two
reacting
partners
form
an
EDA
complex
that
absorbs
light
triggers
the
single-electron
transfer
(SET)
generate
a
thiol
radical,
which
undergoes
addition/cyclization
with
dicyanodiene
through
formation
of
C-S
C-N
bonds.
The Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
89(2), P. 994 - 1009
Published: Jan. 2, 2024
Visible
light-enhanced
[3
+
2]
cycloaddition
of
N,N-disubstituted
hydrazines
with
N-cyano-N-aryl-p-toluenesulfonamides
is
an
efficient
reaction
pathway
to
polysubstituted
1,2,4-triazol-3-amines.
The
performed
under
mild
conditions
without
the
addition
any
transition
metals.
This
strategy
involves
a
C(sp3)–H
bond
activation,
cyano
cycloaddition,
and
formation
two
new
C═N
bonds.
protocol
shows
advantages
good
functional
group
tolerance
broad
substrate
scope.
late-stage
modification
experiments
provide
practical
applications
in
field
organic
synthesis
medicinal
chemistry.
Green Chemistry,
Journal Year:
2023,
Volume and Issue:
25(16), P. 6188 - 6193
Published: Jan. 1, 2023
A
metal-free
photocatalytic
radical
annulation
of
2-cyanoaryl
acrylamides
with
[CF
2
HPPh
3
]
+
Br
−
to
give
4-amino-quinolinones
in
good
yields
was
developed.
An
easily
obtained
organophotocatalyst
and
green
solvent
acetone/H
O
were
utilized
the
protocol.
Advanced Synthesis & Catalysis,
Journal Year:
2023,
Volume and Issue:
366(3), P. 324 - 356
Published: Dec. 14, 2023
Abstract
Elaborated
molecular
architectures,
especially
carbocyclic,
heterocyclic,
endocyclic,
and
polycyclic
structures,
serve
as
an
important
class
of
organic
complexes
because
they
are
frequently
occurring
core
structural
units
in
a
variety
biologically
pharmacologically
relevant
natural
products,
drug
molecules,
agrochemicals,
functional
materials.
A
main
challenge
current
synthetic
approaches
is
the
development
strategically
efficient
selective
formation
these
compounds
from
easy‐to‐handle
starting
The
cascade
cyclizations
1,7‐enynes
have
afforded
indispensable
method
for
accessing
complexity
diversity,
thus
highlighting
their
potential
significance
both
academic
industrial
communities.
In
last
decades,
tremendous
efforts
been
devoted
to
discovering
convenient
routes
access
sophisticated
annulation
derivatives,
wide
range
powerful
straightforward
strategies
reported.
this
review,
latest
achievements
cyclization
reactions
summarized,
which
could
be
separated
into
three
categories:
(1)
Visible‐light‐induced
1,7‐enynes;
(2)
Metal‐free
catalyzed
(3)
Transition‐metal‐catalyzed
1,7‐enynes.
Organic Letters,
Journal Year:
2022,
Volume and Issue:
24(20), P. 3741 - 3746
Published: May 18, 2022
A
Pd(II)-catalyzed
synthesis
of
furopyridines
has
been
developed
from
β-ketodinitriles
and
alkynes
via
an
unusual
N–H/C
annulation.
The
participation
both
the
nitrile
groups
concurrent
construction
furan
pyridine
rings
through
formation
C–C,
C═C,
C–O,
C–N,
C═N
bonds
are
important
features.
synthetic
applicability
is
further
demonstrated
a
series
postsynthetic
alterations.
Organic Letters,
Journal Year:
2025,
Volume and Issue:
unknown
Published: Feb. 2, 2025
Palladium-catalyzed
asymmetric
intermolecular
trans-acetoxypalladation/desymmetric
cyclization/acyl
transfer
cascades
of
alkyne-tethered
malononitriles
with
carboxylic
acids
have
been
demonstrated.
Such
a
sequence
enables
the
formation
multifunctionalized
nitriles
bearing
α-all-carbon
quaternary
stereocenters
high
degree
enantiocontrol
broad
substrate
scope.
Moreover,
synthetic
elaborations
present
these
molecules
as
promising
chiral
building
blocks.
Mechanistic
studies
illustrate
that
cascade
process
proceeds
via
key
imine
intermediate,
and
desymmetric
cyclization
is
enantio-determining
step.
