Angewandte Chemie,
Год журнала:
2024,
Номер
136(8)
Опубликована: Янв. 5, 2024
Abstract
A
mild
photoredox
catalyzed
construction
of
sulfides,
disulfides,
selenides,
sulfoxides
and
sulfones
from
unstrained
ketone
precursors
is
introduced.
Combination
this
deacylative
process
with
S
N
2
or
coupling
reactions
provides
novel
convenient
modular
strategies
toward
unsymmetrical
symmetric
disulfides.
Reactivity
studies
favor
a
bromine
radical
that
initiates
HAT
(Hydrogen
Atom
Transfer)
the
aminal
intermediate
resulting
in
expulsion
C‐centered
intercepted
to
make
C−S
C−Se
bonds.
Gram
scale
reactions,
broad
substrate
scope
tolerance
towards
various
functional
groups
render
method
appealing
for
future
applications
synthesis
organosulfur
selenium
complexes.
The Journal of Organic Chemistry,
Год журнала:
2021,
Номер
87(1), С. 892 - 903
Опубликована: Дек. 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.
Organic Letters,
Год журнала:
2024,
Номер
26(38), С. 8095 - 8099
Опубликована: Сен. 16, 2024
This
work
discloses
a
two-step,
one-pot
approach
to
ω-functionalized
esters
via
cleavage
of
the
alicyclic
fragment
cycloalkanone
semicarbazones.
is
based
on
combination
synthesis
various
alkoxyhydroperoxides
semicarbazone
ozonolysis
and
Organic Letters,
Год журнала:
2021,
Номер
23(5), С. 1809 - 1813
Опубликована: Фев. 24, 2021
The
copper-catalyzed
selective
cleavage
of
alkylsilyl
peroxides
and
the
subsequent
formation
carbon–carbon
or
carbon–nitrogen
bonds
with
organosilicon
compounds
are
described.
reaction
proceeds
under
mild
conditions
exhibits
a
broad
substrate
scope
respect
to
both
cyclic
acyclic
in
combination
carbon
nitrogen
sources.
In
particular,
this
approach
enables
facile
radical
perfluoroalkylation
using
commercially
available
perfluoroalkyltrimethylsilanes.
Our
mechanistic
studies
suggest
that
should
proceed
via
free-radical
process.
Chemical Communications,
Год журнала:
2021,
Номер
57(69), С. 8652 - 8655
Опубликована: Янв. 1, 2021
An
efficient
copper-catalyzed
radical
ring-opening
halogenation
with
HX
(aq)
is
described.
This
protocol
provides
a
practical
access
to
distally
chlorinated,
brominated
and
iodinated
alkyl
ketones
nitriles
moderate
good
yields.
The Journal of Organic Chemistry,
Год журнала:
2021,
Номер
86(17), С. 11987 - 11997
Опубликована: Авг. 10, 2021
A
cheap
iron-catalyzed
C–C
bond
cleavage/thiolation
and
selenylation
of
cycloalkyl
hydroperoxides
are
presented.
This
redox-neutral
protocol
provides
efficient
access
to
diverse
distal
keto-functionalized
thioethers
selenium
compounds.
Remarkably,
only
some
amounts
disulfides
required
for
this
transformation.
Organic Letters,
Год журнала:
2023,
Номер
25(6), С. 928 - 932
Опубликована: Фев. 2, 2023
A
facile
and
efficient
nickel-catalyzed
C-C
bond
cleavage/phosphorylation
of
various
cycloalkyl
hydroperoxides
was
developed.
This
radical
ring-opening
strategy
provided
practical
access
to
structurally
diverse
distal
ketophosphine
oxides
in
one
pot
through
concurrent
C═O/C-P
formation
with
high
atom
economy
under
mild
room
temperature
base-free
conditions.
