The Journal of Organic Chemistry,
Journal Year:
2022,
Volume and Issue:
87(7), P. 4508 - 4523
Published: March 15, 2022
The
scope
of
chemoselective
β-hydride
elimination
in
the
context
arylation/alkenylation
homoenolates
from
cyclopropanol
precursors
using
organoboronic
reagents
as
transmetalation
coupling
partners
was
examined.
reaction
optimization
paradigm
revealed
a
simple
ligand-free
Pd(II)
catalytic
system
to
be
most
efficient
under
open
air
conditions.
preparative
scope,
which
investigated
with
48
examples,
supported
applicability
this
wide
range
substrates
tolerating
variety
functional
groups
while
delivering
β-substituted
enone
and
dienone
derivatives
62-95%
yields.
A
gold(I)-catalyzed
tandem
cyclization/peroxidation
of
2-alkynyl-1-carbonylbenzenes
with
tert-butyl
hydroperoxide
(TBHP)
has
been
successfully
developed
to
access
1-peroxidized
1H-isochromene
derivatives
in
moderate
good
yields.
The
use
one
the
resultant
1H-isochromenes
(3a)
for
construction
phenyl(8-phenylbicyclo[4.2.0]octa-1(6),2,4,7-tetraen-7-yl)methanone
(4),
phenyl(3-phenyl-1,3-dihydroisobenzofuran-1-yl)methanone
(5)
and
2-(2-benzoylphenyl)-1-phenylethan-1-one
(6)
also
investigated,
respectively.
The Journal of Organic Chemistry,
Journal Year:
2025,
Volume and Issue:
unknown
Published: March 16, 2025
A
photocatalytic
radical
sulfonarylation
of
N-arylacrylamides
via
a
three-component
cascade
cyclopropyl
alcohol
ring
opening/sulfur
dioxide
insertion/sulfonyl
addition/cyclization
sequence
has
been
developed.
This
method
employs
alcohols
as
the
precursors
β-carbonyl
alkyl
radicals
and
Na2S2O5
cheap
source
sulfur
dioxide.
By
using
this
procedure,
wide
variety
γ-keto-sulfone-substituted
oxindoles
were
facilely
synthesized.
Organic Letters,
Journal Year:
2025,
Volume and Issue:
unknown
Published: April 27, 2025
A
visible-light-induced
three-component
coupling
of
aldehydes,
1,3-dienes,
and
cyclopropyl
alcohols
using
dual
photoredox
chromium
catalysis
is
herein
described.
This
efficient
protocol
achieves
the
dialkylation
1,3-dienes
toward
1,4-disubstituted
homoallylic
in
moderate
to
good
yields
with
excellent
regioselectivity,
featuring
mild
reaction
conditions,
functional
group
tolerance,
gram-scale
synthesis.
Mechanistic
study
suggests
that
photoinduced
sequential
ring
opening
alcohol
radical
nucleophilic
cascade
addition
are
involved
catalytic
cycle.
The Journal of Organic Chemistry,
Journal Year:
2025,
Volume and Issue:
unknown
Published: May 13, 2025
An
iron-catalyzed
ring-opening
multicomponent
reaction
of
cyclopropyl
alcohols
with
alkenes
and
N-heteroarenes
involving
aryl
C(sp2)-H
functionalization
was
developed.
This
protocol
facilitates
the
regioselective
introduction
both
β-carbonyl
moiety
an
N-heteroarene
group
across
C═C
bond
alkene,
thus
allowing
a
straightforward,
efficient,
facile
access
to
5-heteroarene
ketones.
In
this
process,
strategy
relies
on
alkyl
radical
formation
from
alcohols,
addition
bonds,
heteroaryl
cascades.
general
approach
displays
excellent
selectivity
control
broad
functional-group
tolerance.
The Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
88(19), P. 13553 - 13567
Published: Sept. 14, 2023
Against
the
backdrop
of
well-known
O-sulfonylation
cyclopropyl
alcohols
with
sulfonyl
chlorides,
we
examined
feasibility
conducting
regioselective
C-sulfonylation.
By
emulating
an
umpolung
strategy-guided
design,
report
for
first
time
Cu(II)-catalyzed
β-sulfonylation
cyclopropanols
by
a
mechanism
that
potentially
involves
oxidative
addition
radical
to
metal
homoenolate.
Unlike
reported
methods,
this
protocol
allows
practical
synthetic
route
γ-keto
sulfone
building
blocks
from
leveraging
commercially
available
aryl-
and
alkyl-sulfonyl
common
reagents
in
organic
chemistry
laboratories.
Using
operationally
simple
open-flask
conditions,
preparative
scope
starting
materials
was
demonstrated
using
array
alkyl-substituted
chlorides
(43
examples,
up
96%
yield).
Chemical Communications,
Journal Year:
2021,
Volume and Issue:
57(99), P. 13582 - 13585
Published: Jan. 1, 2021
An
iron(III)
catalyzed
tandem
ring
opening/1,6-conjugate
addition
of
cyclopropanols
to
p-quinone
methides
leading
γ,γ-diaryl
ketones
has
been
described.
This
catalytic
protocol
provides
a
novel
and
efficient
method
access
ketone
derivatives
in
good
excellent
yields
with
high
functional
group
tolerance.
Importantly,
can
be
further
functionalized
give
versatile
set
useful
products.
Organic Letters,
Journal Year:
2023,
Volume and Issue:
25(28), P. 5389 - 5394
Published: July 6, 2023
An
expedient
approach
for
the
synthesis
of
challenging
β-fluoroamides
from
readily
accessible
cyclopropanone
equivalents
is
reported.
Following
addition
pyrazole
used
here
as
a
transient
leaving
group,
silver-catalyzed
regiospecific
ring-opening
fluorination
resulting
hemiaminal
leads
to
β-fluorinated
Asian Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
12(11)
Published: Sept. 7, 2023
Abstract
A
visible
light‐induced
direct
decarboxylative
peroxidation
of
carboxylic
acids
under
mild
conditions
has
been
disclosed.
With
this
protocol,
a
variety
readily
available
were
converted
to
the
products
in
moderate
good
yields
via
radical
C−OO
bond
coupling.
Tert
‐butyl
hydroperoxide
acts
as
both
oxidant
and
peroxyl
source,
avoiding
use
transition
metals
or
extra
oxidants.
