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(15), С. 2955 - 2959
Опубликована: Апрель 3, 2024
An
Eosin
Y-catalyzed
visible
light-promoted
1,4-peroxidation–sulfonylation
of
enynones
was
achieved
to
give
tetrasubstituted
allenes.
The
photoredox
catalysis
Y
allowed
the
concomitant
formation
peroxy
and
sulfonyl
radicals,
where
preferential
radical
addition
alkene
moiety
resulted
in
subsequent
α-keto
radical–sulfonyl
cross
couplings.
developed
demonstrates
a
regioselective
1,4-diradical
strategy,
opening
up
new
possibility
diradical
functionalization
conjugate
systems.
Organic Chemistry Frontiers,
Год журнала:
2023,
Номер
10(19), С. 4941 - 4971
Опубликована: Янв. 1, 2023
A
summary
of
the
various
ring
opening
reactions
strained
and
unstrained
cycloalkanols
is
elaborated
in
present
review.
Key
emphasis
on
reactivities
pertaining
to
cyclopropanols,
cyclobutanols
higher
analogues
provided.
Organic Letters,
Год журнала:
2022,
Номер
24(47), С. 8677 - 8682
Опубликована: Ноя. 17, 2022
Established
herein
is
a
radical-mediated
C–H
alkylation
of
enamides
with
cyclopropanols.
An
environmentally
benign
catalytic
system
iron
salt
and
air
used
to
permit
the
oxidative
coupling
process.
The
protocol
demonstrates
broad
substrate
scope,
allowing
stereoselective
synthesis
alkylated
enamides.
value
this
strategy
further
reflected
by
late-stage
diversification
complex
cyclopropanol-containing
molecules
downstream
transformations.
Mechanistic
studies
reveal
dual
role
in
reaction.
Abstract
Cyclopropanols,
due
to
their
particular
chemistry,
can
participate
in
various
synthetic
reactions
with
retention
or
cleavage
of
the
strained
three‐membered
ring.
Direct
cross‐coupling
ring‐opening
reaction
such
molecules
access
organic
compounds,
as
ketones
has
great
importance
medicinal
chemistry
and
material
sciences.
Hence,
coupling
reaction/cyclization
cyclopropanols
for
constructing
new
valuable
presence
a
transition
metal
catalyst
under
metal‐free
conditions
is
described
this
context.
The
features
are
discussed,
mechanisms
challenging
highlighted.
Organic Process Research & Development,
Год журнала:
2022,
Номер
26(8), С. 2281 - 2310
Опубликована: Авг. 2, 2022
This
review
provides
a
summary
of
recently
published
developments
in
the
field
nonprecious
metal
catalysis
(NPMC)
and
highlights
range
synthetic
applications
captured
research
between
July
October
2021.
is
an
installment
series
on
this
area
briefing
Ni,
Cu,
Fe,
Co
catalysis.
There
has
been
evident
increase
publications
NPMC,
which
indicates
widespread
interest
among
laboratories
academia
industry
development
utilization
catalytic
these
metals.
Organic Letters,
Год журнала:
2023,
Номер
25(12), С. 2058 - 2062
Опубликована: Март 17, 2023
A
Fe(NO3)3-mediated
ring-opening
arylation
of
cyclopropanol
with
the
electron-rich
pyrrole
has
been
developed,
which
might
proceed
through
oxidative
radical
ring
opening
followed
by
cyclization
to
motif
and
then
aromatization.
This
method
enables
direct
without
prefunctionalization
thus
allows
rapid
access
a
diverse
array
chiral
5,6,7,8-tetrahydroindolizines
from
easily
available
amino
acid
esters.
The
synthetic
utility
demonstrated
asymmetric
synthesis
alklaoids
(-)-indolizidine
167B,
(+)-indolizidine
209D,
(+)-monomorine
I,
natural
product
analogue.
Advanced Synthesis & Catalysis,
Год журнала:
2023,
Номер
365(10), С. 1678 - 1684
Опубликована: Апрель 28, 2023
Abstract
A
feasible
and
umpolung
strategy
for
the
synthesis
of
structurally
diverse
β
‐amino
ketones
has
been
achieved
through
TEMPO
mediated
C−N
coupling
cyclopropanols
with
nitrogen
nucleophiles.
Mechanism
studies
indicated
that
in
situ
generated
enones
derived
from
are
key
intermediates
play
multiple
roles,
including
radical
initiator,
trapping
reagent,
a
porter
‐hydrogen
an
base.
This
protocol
features
broad
substrate
scope,
good
scalability
to
excellent
yields
provides
alternative
complementary
approach
important
ketone
scaffolds
under
metal
additive‐free
conditions.
magnified
image
Organic Letters,
Год журнала:
2024,
Номер
26(34), С. 7170 - 7175
Опубликована: Авг. 19, 2024
A
cascade
reaction
of
cyclopropyl
alcohols,
DABSO
(1,4-diazoniabicyclo[2.2.2]octane-1,4-disulfinate),
and
N-(sulfonyl)acrylamides
has
been
developed.
This
tandem
process
went
through
a
cyclopropanol
ring
opening
Michael
addition
sequence.
The
γ-keto
sulfinate
generated
from
the
between
serves
as
nucleophilic
reagent,
N-(sulfonyl)acrylamide
is
used
acceptor.
By
utilizing
this
strategy,
multitudinous
sulfone-bridged
1,7-dicarbonyl
compounds
that
contain
both
β-sulfonyl
amide
unit
sulfone
skeleton
were
conveniently
synthesized.
Advanced Synthesis & Catalysis,
Год журнала:
2023,
Номер
365(7), С. 1072 - 1081
Опубликована: Март 17, 2023
Abstract
Being
in
its
infancy,
radical
cross‐coupling
is
highly
efficient
for
C−C
bond
construction,
though
suffers
from
selectivity
problems
and
limited
reaction
types.
New
methodologies
to
realize
selectively
are
desired.
Herein,
an
iron
catalyzed
deconstructive
cyanomethylation
of
unstrained
cyclic
linear
alcohols
with
acetonitrile
has
been
developed
through
cross‐coupling.
The
unprecedented
method
enables
a
ring‐opening
functionalization
cyclohexanols
produce
α‐cyanomethyl
ketones.
Notably,
the
challenging
involves
twice
single
cleavage
β‐scission
alkoxyl
intermediates,
C(
sp
3
)−H
transformation
via
hydrogen
atom
transfer
(HAT)
procedures,
resulting
two
carbon
species
that
process
form
new
)−C(
)
selectively.
α‐arylketo
α‐aryl
substituted
tertiary
can
also
be
applied
as
substrates,
leading
terminal
cyano‐functionalized
products,
ketone
leaving
fragment.
Mechanistically,
procedure
generate
chlorine
in‐situ
formed
intermediate
cycloalkyl
hypochlorite
was
suggested.
magnified
image
