Advanced Synthesis & Catalysis,
Journal Year:
2023,
Volume and Issue:
365(23), P. 4310 - 4316
Published: Nov. 3, 2023
Abstract
A
Cu(I)‐catalyzed
[4+2]
oxidative
annulation
of
α
,
β
‐unsaturated
ketoxime
acetates
with
cyclopropanols
has
been
developed
for
the
synthesis
2,4,5‐trisubstituted
pyridines
in
28–76%
yields.
This
method
employs
as
C2
synthons
and
features
various
functional
group
compatibility
gram‐scale
synthesis.
In
addition,
a
plausible
reaction
pathway
was
proposed
based
on
mechanism
studies.
European Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
27(9)
Published: Feb. 8, 2024
Abstract
Cycloalkanols
ring‐opening
transformation
is
one
of
the
most
valuable
and
wide
area
research.
Among
numerous
methods
that
have
been
developed,
transition‐metal‐free
approaches
attracted
great
interest
from
both
chemists
pharmacologists.
This
largely
due
to
advantages
being
environmentally
benign,
cost‐effective
operationally
simple.
Here
we
provide
a
comprehensive
outline
on
recent
advances
in
synthesis
distally
substituted
ketones
cyclic
compounds
via
cycloalkanols
under
conditions.
Organic & Biomolecular Chemistry,
Journal Year:
2024,
Volume and Issue:
22(33), P. 6650 - 6664
Published: Jan. 1, 2024
Titanium,
as
an
important
transition
metal,
has
garnered
extensive
attention
in
both
industry
and
academia
due
to
its
excellent
mechanical
properties,
corrosion
resistance,
unique
reactivity
organic
synthesis.
In
the
field
of
photocatalysis,
titanium-based
compounds
such
titanium
dioxide
(TiO
A
TEMPO-mediated
β-ketoalkylation
of
enaminoesters
with
cyclopropanols
under
metal-free
conditions
is
herein
described.
This
reaction
provides
a
straightforward
and
highly
efficient
route
to
β-keto
alkyl
substituted
for
the
first
time,
which
could
be
rapidly
efficiently
converted
into
synthetically
useful
2-alkoxycarbonyl
functionalized
1,5-diketones.
Moreover,
practicability
this
protocol
successfully
demonstrated
by
scale-up
experiments
late-stage
functionalization
natural
products
pharmaceutically
relevant
molecules.
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.
Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(44), P. 9553 - 9557
Published: Oct. 28, 2024
Selective
C–C
bond
cleavage
and
transformation
of
organic
small
molecules
to
create
products
increased
value
are
one
the
central
goals
in
chemistry.
In
this
study,
we
have
developed
a
novel
TEMPO-mediated
ring-opening
α,β-difunctionalization
cyclopropyl
alcohols
with
azides
prepare
structurally
important
4-keto-1,2,3-triazoles
under
metal-
additive-free
conditions.
This
protocol
not
only
provides
straightforward
efficient
method
for
synthesis
4-keto-functionalized
1,2,3-triazoles
pot
but
also
accomplishes
goal
constructing
α,β-double
C–N
bonds
via
ring
opening
first
time.
Additionally,
application
skeletons
drugs
natural
Kv1.5
channel
blocker
4u
further
demonstrate
synthetic
potential
practicability
strategy.
Organic & Biomolecular Chemistry,
Journal Year:
2023,
Volume and Issue:
21(45), P. 8984 - 8988
Published: Jan. 1, 2023
A
metal-free
and
efficient
approach
for
the
synthesis
of
structurally
important
nicotinates
through
4-HO-TEMPO-mediated
[3
+
3]
annulation
cyclopropanols
with
β-enamine
esters
is
presented.
This
protocol
features
high
atom
efficiency,
green
waste,
simple
operation
broad
substrate
scope.
Moreover,
experiments
gram-scale
recovery
oxidants
make
this
strategy
more
sustainable
practical.
Organic & Biomolecular Chemistry,
Journal Year:
2023,
Volume and Issue:
21(25), P. 5171 - 5175
Published: Jan. 1, 2023
A
copper-catalyzed
unprotected
hydroxylamine
mediated
phosphorylation
of
alkenes
furnished
structurally
important
(
E
)-alkenylphosphine
oxides
under
mild
reaction
conditions
with
good
functional
group
tolerance
and
excellent
regioselectivity.
Abstract
The
aerobic
ring‐opening
oxidation
of
cyclopropanols
catalyzed
by
copper
complexes
was
systematically
investigated,
with
a
focus
on
the
effect
nitrogen
ligands
distribution
products.
This
study
led
to
development
new
synthesis
β
‐aminoketones
and
‐enaminones
from
cyclopropanols,
where
product
specificity
is
tuned
through
ligand
solvent
selection.
‐Aminoketones
were
prepared
in
34–99%
yields
copper(II)
acetate‐catalyzed
presence
nucleophilic
secondary
aliphatic
amines.
In
contrast,
bipyridine‐ligated
catalysts
resulted
generation
36–86%
yields,
presumably
via
Kornblum‐DeLaMare
rearrangement
intermediate
1,2‐dioxolanes.
