Organic & Biomolecular Chemistry,
Год журнала:
2023,
Номер
21(32), С. 6493 - 6497
Опубликована: Янв. 1, 2023
In
this
work,
we
wish
to
present
a
nickel-catalyzed
divergent
ring-contraction
and
ring-opening/isomerization
reaction
of
tert-cyclobutanols.
The
key
control
these
two
different
pathways
is
choose
appropriate
boronic
acid,
where
the
use
phenylboronic
acid
pyrimidin-5-ylboronic
enables
ring-opening
reaction/isomerization,
respectively.
Both
cyclopropyl
aryl
methanones
1-aryl
butan-1-ones
could
be
selectively
obtained.
Organic & Biomolecular Chemistry,
Год журнала:
2021,
Номер
19(37), С. 8021 - 8024
Опубликована: Янв. 1, 2021
Nickel-catalyzed
remote
hydrosilylation
of
unconjugated
enones
involving
a
“chain
walking”
process
enables
the
synthesis
Z
-silyl
enol
ethers
as
major
isomers.
Abstract
Here
we
report
a
protocol
for
the
preparation
of
1,4‐diketones
from
1,2‐disubstituted
cyclobutanols
based
on
their
ring‐opening
oxidation
with
molecular
oxygen.
The
reaction
proceeds
under
manganese
catalysis
in
presence
1,10‐phenanthroline
ligand
and
leads
to
target
product
along
minor
4‐hydroxyketone
that
can
be
oxidized
Dess‐Martin
periodinane
same
vessel.
Substrates
alkyl
aryl
substituents
including
those
bearing
functional
groups
were
successfully
engaged
reaction.
European Journal of Organic Chemistry,
Год журнала:
2021,
Номер
2021(35), С. 4958 - 4967
Опубликована: Авг. 12, 2021
Abstract
The
present
work
describes
the
preparation
of
halohydrins
from
2‐halocyclobutanones
by
means
reactions
with
Grignard
reagents
at
−78
°C.
We
discovered
that
prepared
cyclobutanols
underwent
a
thermal
ring‐opening
reaction.
Depending
on
structure
starting
cyclobutanol,
different
products
were
formed.
More
specifically,
1‐substituted
2‐bromocyclobutan‐1‐ol
was
found
to
open
γ‐substituted
butyrophenones.
A
novel
1,3‐dihydro‐2H‐inden‐2‐ylidene
derivative
obtained
for
indene‐derived
cyclobutanols.
Based
outcomes
performed
experiments,
mechanism
can
be
proposed.
Organic & Biomolecular Chemistry,
Год журнала:
2023,
Номер
21(32), С. 6493 - 6497
Опубликована: Янв. 1, 2023
In
this
work,
we
wish
to
present
a
nickel-catalyzed
divergent
ring-contraction
and
ring-opening/isomerization
reaction
of
tert-cyclobutanols.
The
key
control
these
two
different
pathways
is
choose
appropriate
boronic
acid,
where
the
use
phenylboronic
acid
pyrimidin-5-ylboronic
enables
ring-opening
reaction/isomerization,
respectively.
Both
cyclopropyl
aryl
methanones
1-aryl
butan-1-ones
could
be
selectively
obtained.
