Organic Letters,
Journal Year:
2024,
Volume and Issue:
unknown
Published: Dec. 21, 2024
Intramolecular
reactions
between
isocyano
and
iminophosphorane
functions
yield
species
containing
an
embedded
1,3,2-diazaphosphetidine
ring,
as
result
of
the
[2
+
2]
cycloaddition
primary
reactive
product,
cyclic
carbodiimide,
with
a
second
unit
reactant.
DFT
studies
reveal
first
rate-determining
step
entailing
1]
involving
isocyanide
carbon
atom
P═N
double
bond,
further
intervention
dipolar
precursor
intermediate
carbodiimide.
The
ring
final
products
is
shown
to
be
hydrolytically
thermally
labile.
Chemical Communications,
Journal Year:
2023,
Volume and Issue:
59(89), P. 13309 - 13312
Published: Jan. 1, 2023
This
study
describes
an
iron-catalyzed
divergent
oxidation
of
styrene
into
β-hydroxylmethylketone
and
ketone
under
photo-irradiation.
divergence
is
ascribed
to
the
use
with
various
substituents.
More
importantly,
methanol
oxidized
formaldehyde
in
reaction
serves
as
a
C1
synthon.
Mechanism
investigations
show
that
initiated
by
oxidative
SET
transfer
cation
radical.
The
pathway
undergoes
HAT
β-hydride
elimination
well
concerted
cyclization.
Particularly,
several
drug-like
molecules,
such
melperone
analogue,
lenperone
haloperidol
are
synthesized.
In
addition,
this
method
also
applicable
synthesis
natural
product
(R)-atomoxetine.
Organic Chemistry Frontiers,
Journal Year:
2024,
Volume and Issue:
11(6), P. 1775 - 1781
Published: Jan. 1, 2024
We
have
successfully
demonstrated
an
efficient
and
practical
Pd-catalyzed
reaction
between
aziridine
isocyanide,
leading
to
the
synthesis
of
isoindoline
derivatives
in
moderate
good
yields.
Organic Chemistry Frontiers,
Journal Year:
2023,
Volume and Issue:
10(22), P. 5559 - 5567
Published: Jan. 1, 2023
A
novel
divergent
synthetic
method
for
polysubstituted
pyrroles
from
isocyanides
and
α,β-unsaturated
ketones
in
the
presence
of
a
rhodium
catalyst
bis(pinacolato)diboron
(B
2
pin
)
is
described
here.
Organic & Biomolecular Chemistry,
Journal Year:
2023,
Volume and Issue:
22(2), P. 252 - 268
Published: Nov. 28, 2023
Eight-membered
heterocycles
are
important
but
their
synthesis
is
usually
challenging.
This
review
summarizes
the
recent
advances
in
[4
+
4]
annulation
of
conjugated
heterodienes
with
1,4-dipolar
species
for
assembling
eight-membered
heterocycles.
Organic Letters,
Journal Year:
2023,
Volume and Issue:
25(34), P. 6272 - 6277
Published: Aug. 21, 2023
An
unprecedented
route
for
the
preparation
of
fused
tetracyclic
N-heterocycles
is
presented
through
palladium-catalyzed
cyclization
isocyanides
with
alkyne-tethered
aryl
iodides.
In
this
transformation,
a
novel
amino-to-alkyl
1,5-palladium
migration/intramolecular
C(sp3)-C(sp2)
coupling
sequence
was
observed
first.
More
importantly,
isocyanide
exhibited
three
roles,
serving
simultaneously
as
C1
synthon,
C1N1
and
donor
C(sp3)
coupling,
reaction
sole
successful
example
that
achieved
C(sp3)-H
activation
isocyanide.
Tetrahedron Chem,
Journal Year:
2023,
Volume and Issue:
9, P. 100056 - 100056
Published: Dec. 9, 2023
Complexation
of
Lewis
acids
to
electrophiles
triggers
the
sequential
insertion
two
or
more
isocyanides
resulting
in
valuable
iminonitriles
heterocycles.
The
number
insertions
is
controlled
by
nature
alkyl-
arylisocyanide
and
presence
a
proximal
nucleophile
capable
attacking
intermediate
nitrilium;
loss
an
alkyl
group
from
nitrilium
attack
terminates
further
isocyanide
insertions.
mechanistic
survey
protic
acid-promoted
aims
provide
fundamental
understanding
reactivity
selectivity
facilitate
synthetic
applications.
review
structured
with
introductory
overview
followed
analysis
before
moving
double
insertions,
which
are
most
prevalent,
then
triple
insertions;
concludes
sole
example
quadruple
insertion.
hope
that
insight
contained
will
aid
applying
acid-activated
prepare
array
complex
Abstract
2‐(chalcogen)benzothiazoles
are
frequently
used
as
core
structures
for
the
development
of
pharmaceutical
agents.
A
strategy
synthesis
under
electrooxidative
conditions
using
isocyanides,
thiols
or
diselenides
substrates
was
developed.
This
protocol
allows
access
to
structurally
diverse
in
good
yields
and
with
functional
group
tolerance,
which
does
not
require
heavy
metal
catalysts
exogenous
oxidants.
Furthermore,
gram‐scale
performed
demonstrate
scale‐up
applicability
this
reaction.
Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(30), P. 6335 - 6340
Published: July 24, 2024
An
unprecedented
trimethylsilyl
trifluoromethanesulfonate
(TMSOTf)-promoted
selective
double
insertion
of
isocyanides
into
aldehydes
was
developed,
providing
an
efficient
protocol
for
synthetically
challenging
β-carbonyl
α-iminoamides.
The
given
approach
is
applicable
a
diverse
selection
readily
accessible
aldehydes,
along
with
serving
as
essential
precursors
"amide"
and
"imine"
scaffolds.
versatile
transformations
the
products
were
demonstrated,
pivotal
intermediates
plausible
mechanism
identified.
New Journal of Chemistry,
Journal Year:
2024,
Volume and Issue:
48(6), P. 2639 - 2648
Published: Jan. 1, 2024
A
palladium-catalyzed
and
amide-assisted
multicomponent
reaction
of
3-diazo
oxindole,
isocyanide,
water
to
generate
biologically
important
oxazole-fused
indole
scaffolds
has
been
reported.
