Asian Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
13(11)
Published: Aug. 23, 2024
Abstract
Cu‐
and
Fe‐
catalyzed
trideuteromethylation
reactions
using
alkylsilyl
peroxide
as
trideuteromethyl
radical
precursor
are
reported.
The
was
synthesized
from
acetone‐d6
in
a
three‐step
sequence,
the
with
various
coupling
partners
afforded
efficiently
corresponding
N−CD
3
,
O−CD
C−CD
bond
formation
products.
heptadeuteriopropylation
prepared
butyric
acid‐d7
is
also
described.
Trends in Chemistry,
Journal Year:
2023,
Volume and Issue:
5(3), P. 174 - 200
Published: Feb. 14, 2023
Organic
peroxides
are
becoming
popular
intermediates
for
novel
chemical
transformations.
The
weak
O-O
bond
is
readily
reduced
by
transition
metals,
including
iron
and
copper,
to
initiate
a
radical
cascade
process
that
breaks
C-C
bonds.
Great
potential
exists
the
rapid
generation
of
complexity,
originating
from
ability
couple
resulting
free
radicals
with
wide
range
partners.
First,
this
review
article
discusses
history
synthesis
organic
peroxides,
providing
context
necessary
understand
methodology.
Then,
it
highlights
91
examples
recent
applications
functionalization
bonds
accessed
through
metal-mediated
reduction
peroxides.
Finally,
we
provide
some
comments
about
safety
when
working
Organometallics,
Journal Year:
2023,
Volume and Issue:
42(18), P. 2598 - 2612
Published: March 1, 2023
The
reaction
of
Ni(II)
acetate
with
diacyl
peroxides
produces
high-valence
Ni-species
capable
catalytic
oxidative
acyloxylation
C(sp3)–H
bonds
in
ethers,
ketones,
and
alkanes.
desired
esters
were
obtained
20–82%
yields.
Computational
analysis
suggests
that
activation
the
peroxide
moiety
a
dynamically
interconverting
mixture
formal
Ni(III)
state.
Remarkably,
these
species,
coordination
RCO2
group
at
Ni
preserves
radical
character
carboxylate
(i.e.,
acts
as
an
“L-ligand”),
so
latter
can
induce
fast
C–H
abstraction.
spirocyclopropyl
prevents
premature
decarboxylation
via
combination
hybridization
factors
stereoelectronic
effects.
A
variety
viable
patterns
identified
experimentally
computationally.
Green Chemistry,
Journal Year:
2022,
Volume and Issue:
24(24), P. 9373 - 9401
Published: Jan. 1, 2022
This
review
covers
the
recent
progress
in
electrochemically
enabled
radical-mediated
aryl/alkenyl
C(sp
2
)–C(sp
3
)
cross-coupling
reactions,
including
synthetic
strategies,
plausible
mechanisms
and
further
research
outlook.
The Journal of Organic Chemistry,
Journal Year:
2021,
Volume and Issue:
87(1), P. 892 - 903
Published: Dec. 27, 2021
Herein
we
demonstrate
the
first
successful
application
of
cycloalkyl
silyl
peroxides
(CSP)
as
an
electrophilic
coupling
partner
in
cross-electrophile
reaction.
Diverse
CSP
are
efficiently
cross-coupled
with
array
α-trifluoromethyl
alkenes
under
catalysis
nickel
assistance
zinc
reducing
agent.
This
method
allows
use
unstrained
carbonyl-containing
alkyl
source
allylic
defluorinative
reaction,
to
access
a
variety
gem-difluoroalkenes
bearing
pendent
ketone
moiety
high
functionality
tolerance.
Chemical Science,
Journal Year:
2024,
Volume and Issue:
15(13), P. 4757 - 4762
Published: Jan. 1, 2024
α-Keto-,
β-acetoxy-
and
β-amidoalkylsilyl
peroxides
are
prepared
from
various
precursors
utilized
for
Fe-catalyzed
visible-light-promoted
radical
functionalization
with
coupling
partners
under
mild
conditions
a
broad
substrate
scope.
Chemical Communications,
Journal Year:
2023,
Volume and Issue:
59(88), P. 13175 - 13178
Published: Jan. 1, 2023
An
NHC
organocatalytic
radical
acylation
of
cycloalkyl
silyl
peroxides
with
aldehydes
was
developed
for
the
efficient
and
rapid
synthesis
long-chain
1,6-/1,7-/1,8-diketones,
especially
unsymmetrical
ones.
The Journal of Organic Chemistry,
Journal Year:
2022,
Volume and Issue:
87(13), P. 8824 - 8834
Published: June 22, 2022
An
Fe(OTf)2-catalyzed
three-component
coupling
reaction
of
α,β,γ,δ-unsaturated
carbonyl
compounds
with
alkylsilyl
peroxides
in
the
presence
certain
heteronucleophiles
(ROH
and
indole)
is
realized
under
mild
conditions.
A
variety
α,β,γ,δ-diene
substrates
different
substituents
were
successfully
employable
via
combination
several
peroxides.
This
new
approach
also
applicable
to
double
functionalization
diene
substrates.
Organic Letters,
Journal Year:
2022,
Volume and Issue:
24(14), P. 2641 - 2645
Published: March 4, 2022
The
formation
of
two
carbon-carbon
bonds
using
vinylarenes
with
alkylsilyl
peroxides
and
β-keto
carbonyl
substrates
is
effected
by
the
presence
catalytic
Fe(OTf)2
under
mild
reaction
conditions.
A
variety
different
substituents
can
be
utilized
in
combination
several
substrates.
