Chemical Science,
Journal Year:
2025,
Volume and Issue:
unknown
Published: Jan. 1, 2025
A
photoredox
nucleophilic
radical
strain-release/[3,3]-rearrangement
cascade
has
been
established
for
the
synthesis
of
polysubstituted
cyclobutanes
by
using
bicyclo[1.1.0]butanes/cyclobutenes
as
acceptors
and
α-silylamines
donors.
Tetrahedron Chem,
Journal Year:
2024,
Volume and Issue:
9, P. 100070 - 100070
Published: Feb. 28, 2024
Bicyclo[1.1.0]butanes
(BCBs)
and
[1.1.1]propellanes
(tricyclo[1.1.1.01,3]pentanes,
TCPs)
are
structurally
unique
compounds
with
different
chemical
properties.
Strain-release
driven
reactions
have
emerged
as
an
atom-
step-economic
strategy
for
the
organic
synthesis.
Using
this
strategy,
a
variety
of
functional
ring
molecules
been
efficiently
synthesized,
including
various
cyclobutane
molecules,
bicyclo[2.1.1]hexanes,
bicyclo[1.1.1]pentanes,
others.
More
specifically,
these
strain
release-driven
include
aspects
nucleophilic
addition,
radical
electrophilic
or
transition
metal
catalysis.
This
review
will
discuss
recent
developments
in
strain-release
transformations
bicyclo[1.1.0]butanes
[1.1.1]propellanes.
Organic Letters,
Journal Year:
2025,
Volume and Issue:
unknown
Published: Feb. 17, 2025
A
metal-free
photosensitized
1,2-imino-thiocyanation
of
olefins
has
been
established
by
using
the
easily
accessible
bifunctional
reagent
S-cyano-N-(diphenylmethylene)
thiohydroxylamine.
wide
range
were
successfully
transformed
into
corresponding
β-iminothiocyanates
in
moderate
to
high
yields.
This
protocol
stands
out
for
its
nature,
broad
substrate
compatibility,
and
atom
step
economy,
providing
an
effective
strategy
assembling
β-amino
thiocyanate-containing
scaffolds.
Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(10), P. 2073 - 2078
Published: March 6, 2024
A
visible-light-induced
radical
alkylarylation
of
N-aryl
bicyclobutyl
amides
with
α-carbonyl
alkyl
bromides
for
the
synthesis
functionalized
3-spirocyclobutyl
oxindoles
is
described
in
which
β-selective
addition
to
forms
a
key
intermediate
followed
by
interception
intrinsic
arene
functional
group.
This
approach
can
be
applicable
wide
range
bromides,
including
primary,
secondary,
and
tertiary
α-bromoalkyl
esters,
ketones,
nitriles,
nitro
compounds.
Chemical Science,
Journal Year:
2024,
Volume and Issue:
15(31), P. 12473 - 12479
Published: Jan. 1, 2024
Bicyclo[1.1.0]butanes
(BCBs),
featuring
two
fused
cyclopropane
rings,
have
found
widespread
application
in
organic
synthesis.
Their
versatile
reactivity
towards
radicals,
nucleophiles,
cations,
and
carbenes
makes
them
suitable
for
various
reactions,
including
ring-opening
annulation
strategies.
Despite
this
versatility,
their
potential
as
enophiles
an
ene
reaction
remains
underexplored.
Considering
given
the
challenges
of
achieving
diastereoselectivity
reactions
BCBs,
herein,
we
present
a
unique
method
utilizing
BCBs
mild
diastereoselective
Sc(OTf)
Chemical Science,
Journal Year:
2023,
Volume and Issue:
15(9), P. 3182 - 3191
Published: Dec. 21, 2023
Two
complementary
strain-enabled
radical
spirocyclization
cascades
have
been
realized
to
synthesize
spirocyclobutyl
lactones
and
–
lactams.
The
reactions
operate
under
mild
conditions
demonstrate
excellent
functional
group
compatibility.
The
exploration
of
C(sp3)-rich
three-dimensional
(3D)
scaffolds
as
bioisosteres
for
planar
aromatics
has
garnered
increasing
attention.
While
the
bioisosterism
benzenes
been
extensively
studied,
pyridines,
second
most
prevalent
aromatic
compounds
in
pharmaceuticals,
faces
additional
challenges
and
encountered
surprisingly
limited
success.
In
this
study,
we
propose
unprecedented
2-azabicyclo[3.1.1]heptenes
effective
1,3,5-trisubstituted
pyridines
terms
not
only
3D
conformation
but
also
basicity.
We
develop
a
pyridine-boryl
radical-catalyzed
[3π
+
2σ]
cycloaddition
reaction
vinyl
azides
with
bicyclo[1.1.0]butanes
(BCBs)
an
efficient
synthetic
approach.
Synthetic
manipulation
products
reveals
valuable
handles,
allowing
modular
synthesis
various
pyridine
bioisosteres.