The Journal of Organic Chemistry,
Год журнала:
2022,
Номер
87(7), С. 4508 - 4523
Опубликована: Март 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.
Organic Letters,
Год журнала:
2024,
Номер
26(30), С. 6314 - 6319
Опубликована: Июль 22, 2024
The
regio-/stereoselective
synthesis
of
vinyl
cyclobutanols
from
alkynyl
is
demonstrated.
Here,
selective
C-C
bond
activation
the
cyclopropyl
alcohol
ring
has
been
achieved
in
presence
cyclobutanol
ring.
KIE
experiments
indicated
noninvolvement
O-H
oxidative
addition
step
rate-determining
step.
Further,
applicability
these
for
1,4-diketones
and
1,6-diketone
The Journal of Organic Chemistry,
Год журнала:
2020,
Номер
86(1), С. 466 - 474
Опубликована: Ноя. 30, 2020
Herein,
we
first
present
a
nickel-catalyzed
arylation
and
alkenylation
of
tert-cyclobutanols
with
aryl/alkenyl
triflates
via
C–C
bond
cleavage.
An
array
γ-substituted
ketones
was
obtained
in
moderate-to-good
yields,
thus
featuring
earth-abundant
nickel
catalysis,
broad
substrate
scope,
simple
reaction
conditions.
Preliminary
mechanistic
experiments
indicated
that
β-carbon
elimination
pathways
might
be
involved
the
catalytic
cycle.
The Journal of Organic Chemistry,
Год журнала:
2022,
Номер
87(7), С. 4508 - 4523
Опубликована: Март 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.
