European Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
27(44)
Published: Oct. 24, 2024
Abstract
Organic
transformations
initiated
by
photochemical
activation
have
been
at
the
forefront
of
reaction
discovery.
In
this
study,
we
present
a
formal
[3+2]
and
[4+2]
cycloaddition
using
N
‐aryl
cyclopropylamines
cyclobutylamines
in
conjunction
with
α
,
β
‐unsaturated
carbonyl
systems,
unveiling
two
distinct
mechanistic
pathways.
The
is
elucidated
as
being
guided
activity
an
electron
donor‐acceptor
(EDA)
complex.
Simultaneously,
intermolecular
annulation
cyclobutylanilines
achieved
visible‐light
photoredox
catalysis.
These
simple
methodologies
wide
applicability,
facilitating
synthesis
‐arylaminocycloalkyl
compounds
yields
ranging
from
good
to
excellent.
Organic Letters,
Journal Year:
2023,
Volume and Issue:
25(24), P. 4551 - 4555
Published: June 12, 2023
An
enantioselective
intermolecular
[3
+
2]
cycloaddition
of
N-arylcyclopropylamines
with
2-aryl
acrylates/ketones
and
cyclic
ketone-derived
terminal
olefins
via
asymmetric
photoredox
catalysis
is
reported.
A
dual
catalyst
system
involving
DPZ
a
chiral
phosphoric
acid
effective
for
the
transformations,
leading
to
wide
array
valuable
cyclopentylamines
high
yields,
ee's,
drs.
Among
them,
elaborate
modulation
ester
group
acrylates
was
shown
be
in
improving
reactivity,
thereby
enabling
success
transformations.
Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(15), P. 3151 - 3157
Published: April 2, 2024
A
facile
iron(II)-catalyzed
radical
[3
+
2]
cyclization
of
N-aryl
cyclopropylamines
with
various
alkenes
to
access
the
structurally
polyfunctionalized
cyclopentylamine
scaffolds
has
been
developed.
Using
low-cost
FeCl2·4H2O
as
catalyst,
could
be
utilized
react
a
wide
range
including
exocyclic/acyclic
terminal
alkenes,
cycloalkenes,
from
natural-occurring
compounds
(Alantolactone,
Costunolide),
and
known
drugs
(Ibuprofen,
l-phenylalanine,
Flurbiprofen)
obtain
variety
cyclopentylamines
fused
different
useful
motifs
in
generally
good
yields
diastereoselectivities.
The
highlight
this
protocol
is
also
featured
by
no
extra
oxidant,
base,
EtOH
solvent,
gram-scale
synthesis,
further
diverse
transformations
synthetic
products.
More
importantly,
an
iron(II)-mediated
hydrogen
dissociation
pathway
was
proposed
based
on
mechanism
research
experiments.
Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(15), P. 3294 - 3298
Published: April 3, 2024
A
(3
+
3)
annulation
of
aminocyclopropanes
and
vinyldiazo
compounds
enabled
by
organo-photocatalysis
is
described.
The
reaction
allows
the
regioselective
synthesis
cyclohexenes
bearing
adjacent
amino
carbonyl
groups
with
broad
functional
group
tolerance.
In
a
departure
from
previous
reports,
our
work
demonstrated
that
distonic
radical
cation
can
be
preferentially
intercepted
weakly
nucleophilic
compounds,
followed
an
exclusive
6-endo
cyclization
for
ring
closure.
Based
on
interaction
between
ester
groups,
products
further
converted
to
cyclohexene-fused
1,3-oxazinane
azetidine.
The Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
89(1), P. 57 - 67
Published: Dec. 18, 2023
A
general
and
efficient
CuI/N-carbazolyl-1H-pyrrole-2-carbohydrazide
catalyst
system
was
developed
for
the
N-arylation
of
cyclopropylamine
using
aryl
bromides
at
room
temperature.
Herein,
5
mol
%
CuI
ligand
were
used
to
synthesize
N-aryl
cyclopropylamines
in
moderate
excellent
yields.
This
protocol
scaled
up
produce
desired
product
gram
levels
has
been
generalized
C–N
coupling
between
amines
Molecules,
Journal Year:
2023,
Volume and Issue:
28(17), P. 6237 - 6237
Published: Aug. 25, 2023
1,4-Benzothiazines
are
the
main
building
blocks
of
naturally
occurring
pheomelanin
pigments,
and
their
chromophoric
properties
have
been
strongly
related
to
well-known
phototoxicity
these
partly
responsible
for
high
incidence
melanoma
other
skin
cancers
in
red-haired
people.
However,
some
peculiar
features
1,4-benzothiazine
chromophore
could
be
functionally
exploited
several
sectors.
Within
this
context,
perspective,
an
overview
very
recently
reported
applications
pH
sensing,
filter
permeability
control,
smart
packaging,
electrochromic
device
fabrication,
bioimaging,
photocatalysis,
HPLC
detection
systems
is
provided,
together
with
a
brief
presentation
developed
synthetic
approaches
scaffold,
aim
emphasizing
still-undervalued
multifunctional
opportunities
offered
by
class
compounds.
Organic & Biomolecular Chemistry,
Journal Year:
2023,
Volume and Issue:
21(22), P. 4637 - 4642
Published: Jan. 1, 2023
We
have
developed
a
visible-light-mediated
formal
[4
+
2]
cycloaddition
of
arylcyclobutylamines
with
olefins,
using
QXPT-NPhCN
as
an
organic
photocatalyst.
The
corresponding
cycloadducts
could
be
obtained
from
electron-deficient
aryl
olefins
and
exocyclic
olefins.
found
that
the
addition
K3PO4
significantly
promote
cycloadditions.
Using
this
method,
2-functionalized
cyclohexylamines
including
ones
spiro-skeletons
can
expediently
obtained.
Based
on
"3D-bioisostere"
principle,
we
designed
synthesized
three
cyclohexylamine
2-sulfonylurea
compounds.
Two
cyclopropyl
substituted
nitrenium
ions
were
generated
through
photolysis
of
their
corresponding
N-aminopyridinium
ion
photoprecursors.
In
the
case
N-biphenyl-N-cyclopropyl
(5).
Stable
products
are
derived
from
a
combination
ring
expansion,
forming
N-biphenylazetium
ion,
and
ethylene
elimination,
biphenylisonitrilium
ion.
When
present
in
high
concentrations,
methanol
can
add
to
N-3-methoxypropyl-N-biphenyl
iminium
contrast,
only
detectable
product
N-benzyl-N-cyclopropyl
(6)
is
benzylisonitrile,
resulting
elimination
ethylene.
DFT
calculations
predict
distributions
more
stable
biphenyl
system
5
with
reasonable
accuracy.
However
less
benzyl
6
forecast
Organic Chemistry Frontiers,
Journal Year:
2024,
Volume and Issue:
11(23), P. 6712 - 6717
Published: Jan. 1, 2024
A
visible
light-promoted
synthesis
route
to
fused
tetracyclic
skeletons
with
rich
sp
3
carbons
through
stepwise
radical
cycloadditions
and
further
cyclization
of
the
final
intermediates
adjacent
aromatic
rings
was
developed.
Chemical Communications,
Journal Year:
2023,
Volume and Issue:
59(97), P. 14423 - 14426
Published: Jan. 1, 2023
A
visible-light-induced
cycloaddition
between
2-alkenylarylisocyanides
and
cyclopropylanilines
is
reported.
This
cascade
radical
reaction
constructs
two
new
C-C
bonds
rings
to
afford
3-aminotetrahydro-1H-carbazols
with
high
atom
step
economy.
The
mechanism
rationalized
as
involving
sequential
distonic
cation
formation/isocyanide
insertion/5-exo-trig
cyclization/intramolecular
iminium
ion
addition/tautomerization.
