Copper-Catalyzed 1,2-Sulfonyletherification of 1,3-Dienes
Organic Letters,
Год журнала:
2024,
Номер
26(15), С. 2939 - 2944
Опубликована: Апрель 11, 2024
A
selective
three-component
1,2-sulfonyl
etherification
of
aryl
1,3-dienes
enabled
by
copper
catalysis
to
afford
biologically
interesting
alkenyl
1,2-sulfone
ether
derivatives
through
C–S
and
C–O
bond
formation
is
described.
The
protocol
proceeds
with
the
sulfonyl
chloride
alcohols
under
simple,
mild,
base-free
conditions,
providing
a
straightforward
route
sulfonylated
allyl
compounds
broad
functional
group
tolerance
excellent
chemo-
regioselectivity.
Mechanistic
studies
indicate
that
alkene
difunctionalization
includes
key
copper-mediated
single-electron
transfer
process.
Язык: Английский
Copper-Catalyzed Regioselective 1,4-Sulfonyl Indolylation of 1,3-Dienes with Sulfonyl Chloride and Indoles
Organic Letters,
Год журнала:
2025,
Номер
unknown
Опубликована: Фев. 22, 2025
A
copper-based
catalytic
system
has
been
described
to
enable
the
efficient
1,4-sulfonylindolylation
of
1,3-dienes
with
sulfonyl
chloride
and
indoles.
This
protocol
offers
a
practical
method
for
synthesis
allylsulfone-containing
indole
derivatives
broad
range
compatible
functionalities
excellent
chemo-
regioselectivities.
Mechanistic
studies
suggest
that
copper
catalyst
plays
dual
role
initiating
radicals
prompting
coupling
in
this
conjugated
diene-selective
1,4-difunctionalization
strategy.
Язык: Английский
Rapid Access to γ,γ‐Dichloroketones via Radical‐Induced Dichloromethylation and Concomitant 1,2‐Aryl Migration of Allylic Alcohols with CHCl3
Advanced Synthesis & Catalysis,
Год журнала:
2023,
Номер
365(22), С. 3843 - 3848
Опубликована: Окт. 10, 2023
Abstract
A
radical‐induced
dichloromethylation
and
concomitant
1,2‐aryl
migration
of
allylic
alcohols
with
CHCl
3
is
developed
for
the
construction
γ,γ‐dichloroketones
in
moderate
to
good
yields.
We
found
that,
para
‐substituted
unsymmetrical
substrates,
more
electron‐deficient
aryl
group
migrates
preferentially
over
electron‐rich
group.
Moreover,
chlorocyclopropanes
could
be
obtained
from
allyl
one‐pot
manner
through
radical‐addition/1,2‐aryl
migration/nucleophilic
substitution.
Язык: Английский
Advances in radical peroxidation with hydroperoxides
Beilstein Journal of Organic Chemistry,
Год журнала:
2024,
Номер
20, С. 2959 - 3006
Опубликована: Ноя. 18, 2024
Organic
peroxides
have
become
sought-after
functionalities,
particularly
following
the
multi-tone
consumption
in
polymer
production
and
success
medicinal
chemistry.
The
selective
introduction
of
a
peroxide
fragment
at
different
positions
on
target
molecule
is
priority
modern
reaction
design.
pioneering
Kharasch-Sosnovsky
peroxidation
became
basic
universal
platform
for
development
methods,
with
its
great
potential
rapid
generation
complexity
due
to
ability
couple
resulting
free
radicals
wide
range
partners.
This
review
discusses
recent
advances
radical
Kharasch-type
functionalization
organic
molecules
OOR
including
free-component
couplings.
discussion
has
been
structured
by
type
substrate
peroxidation:
C(sp
Язык: Английский
TBHP‐Mediated Hydroxyperfluoroalkylation of Alkenes with Perfluoroalkyl Iodides to Construct β‐Perfluoroalkyl Alcohols
Advanced Synthesis & Catalysis,
Год журнала:
2024,
Номер
366(17), С. 3572 - 3577
Опубликована: Апрель 10, 2024
Abstract
A
three‐component
strategy
for
the
synthesis
of
β‐perfluoroalkyl
allyl
alcohols
from
1,3‐dienes
is
developed.
diverse
range
synthetically
valuable
are
obtained
in
moderate
to
high
yields.
Broad
substrate
scope
and
good
functional
group
tolerance
observed.
This
method
also
applicable
mono‐olefins
1,3‐enynes.
The
control
experiment
results
demonstrate
that
hydroxyl
OH
product
comes
TBHP.
In
addition,
practicality
mild
reaction
conditions
make
these
synthetic
transformations
attractive
organic
synthesis.
Язык: Английский
TMSCN-Promoted Difunctionalization of Alkenes for the Synthesis of Alcohol Derivatives
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(17), С. 12062 - 12070
Опубликована: Авг. 15, 2024
A
TMSCN-promoted
difunctionalization
of
styrenes
with
CHCl3
and
TBHP
is
reported
via
the
radical
addition/cross
coupling
process.
wide
range
dichloromethyl-substituted
alcohol
derivatives
were
synthesized
under
transition-metal-free
conditions.
Besides,
this
method
also
applicable
to
unactive
alkenes.
The
key
success
lies
in
role
TMSCN,
which
prevents
reaction
toward
dichloromethylperoxylation
olefins.
This
represents
an
alternative
approach
for
synthesizing
diverse
using
readily
available
substrates,
holding
significant
promise
fields
pharmaceutical
chemistry
natural
product
synthesis.
Язык: Английский
Three-Component 1,2-Dioxygenation of 1,3-Dienes Using Carboxylic Acids and TEMPO
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(22), С. 16865 - 16872
Опубликована: Ноя. 4, 2024
A
mild,
metal-free
1,2-dioxygenation
of
1,3-dienes
using
TEMPO
and
carboxylic
acids
is
reported.
This
method
includes
examples
for
a
variety
as
well
aliphatic
aromatic
acids.
reaction
also
demonstrates
complete
site-
regioselectivity
in
the
oxygen
addition.
Furthermore,
extensive
derivatization
differential
groups
product
has
been
demonstrated,
including
reduction
remaining
alkene
to
access
alkyl,
vicinally
dioxygenated
scaffolds.
Finally,
this
shown
both
experimentally
computationally
occur
through
acid-driven
disproportionation
TEMPO.
Язык: Английский
Amine-Promoted Three-Component Radical Selenofunctionalization for the Construction of β-Hydroxy Selenide Derivatives
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
unknown
Опубликована: Дек. 28, 2024
An
amine-promoted
three-component
radical
selenofunctionalization
reaction
of
alkenes
with
TBHP
and
diselenide
is
disclosed.
The
conditions
are
mild
suitable
for
a
wide
range
substrates
(29
examples),
all
give
the
corresponding
hydroxyselenenylation
products
in
moderate
to
excellent
yields.
In
addition,
preliminary
studies
on
mechanism
reveal
that
current
method
might
proceed
via
pathway.
serves
as
both
initiator
source
hydroxyl
group.
Язык: Английский