Advanced Synthesis & Catalysis,
Год журнала:
2022,
Номер
364(18), С. 3316 - 3320
Опубликована: Авг. 20, 2022
Abstract
A
photoredox
and
copper‐catalyzed
sulfonylphosphorothiolation
of
alkenes
has
been
developed.
With
the
use
readily
available
aryl
or
alkyl
sulfonyl
chlorides
as
radical
precursors
(RO)
2
P(O)SH
coupling
partners,
a
wide
range
decorated
β‐sulfonyl
phosphorothioates
could
be
obtained
in
37–98%
yields
with
good
functional
group
tolerance.
Importantly,
this
three‐component
reaction
can
conveniently
extended
to
late‐stage
modification
bioactive
molecules
gram‐scale
synthesis.
magnified
image
RSC Advances,
Год журнала:
2022,
Номер
12(26), С. 16745 - 16750
Опубликована: Янв. 1, 2022
A
metal-
and
base-free
5-endo-trig
sulfonylative
cyclization
between
1,5-dienes,
aryldiazonium
salts
SO2
(from
SOgen)
is
presented.
This
method
could
successfully
produce
sulfonylated
pyrrolin-2-ones
in
one
pot
with
excellent
regioselectivity
good-to-excellent
yields.
strategy
features
mild
reaction
conditions
broad
substrate
scope.
Moreover,
a
scale-up
three
synthetic
applications
demonstrate
the
practicality
of
this
method.
Lastly,
control
experiments
indicate
that
may
proceed
radical
pathway.
Sulfone
motifs
play
important
roles
in
bioactive
compounds
and
functional
materials.
The
development
of
efficient
methodologies
for
constructing
sulfonyl-containing
has
thus
attracted
considerable
attention.
Here,
we
introduce
a
protocol
the
preparation
alkyl
aryl
sulfones
under
mild
conditions.
This
employs
β-thioamide
sulfone
as
novel
motif
donor.
It
forms
sulfinates
situ
basic
conditions,
which
then
undergo
cross-coupling
with
intermediates
that
were
generated
from
ligand-free
copper-catalyzed
cyclopropenes
(CPEs)
ring
opening.
A
new
three-component
1,2-perfluoroalkyl
trifluoromethylthiolation
of
alkenes
via
dual
photoredox/copper
catalysis
has
been
established,
affording
a
variety
CnF2n+1/CF3S-containing
molecules
under
mild
conditions
in
redox-neutral
manner.
This
protocol
exhibits
excellent
functional
group
tolerance,
broad
compatibility
with
various
and
perfluoroalkyl
iodides,
potential
utility
the
modification
bioactive
molecules.
Organic Letters,
Год журнала:
2023,
Номер
25(28), С. 5333 - 5338
Опубликована: Июль 13, 2023
An
efficient
and
novel
visible-light-induced
oxo-amination
of
terminal
alkenes
for
the
construction
α-amino
ketones
with
easily
accessible
green
O2
as
oxygen
source
has
been
developed.
The
transformation
possesses
advantages
operational
simplicity,
a
broad
substrate
scope,
high
atom
economy,
mild
reaction
conditions.
mechanistic
studies
reveal
that
an
energy
transfer
process
probably
occurs
in
initial
stage,
proceeds
via
β-scission
alkoxyl
radical
species.
Organic Chemistry Frontiers,
Год журнала:
2024,
Номер
11(15), С. 4275 - 4283
Опубликована: Янв. 1, 2024
A
copper-catalyzed
enantioselective
four-component
reaction
via
the
insertion
of
sulfur
dioxide
toward
synthesis
chiral
sulfones
bearing
an
all-carbon
quaternary
stereocenter
at
β
position
is
reported.
Organic Letters,
Год журнала:
2022,
Номер
24(41), С. 7560 - 7565
Опубликована: Окт. 12, 2022
An
iron-catalyzed
four-component
sulfonylthiocyanation
between
α,β-unsaturated
amides/esters,
TMSNCS,
aryldiazonium
tetrafluoroborates,
and
sulfur
dioxide
(from
SOgen)
is
demonstrated.
This
protocol
characterized
by
mild
reaction
conditions,
good
functional
group
compatibility,
broad
substrate
scope,
to
excellent
yields,
providing
a
feasible
method
for
the
preparation
of
β-thiocyanated
sulfone
compounds.
The
preliminary
mechanism
investigation
shows
that
radical
pathway
may
be
involved
in
process.
Advanced Synthesis & Catalysis,
Год журнала:
2022,
Номер
364(23), С. 4020 - 4025
Опубликована: Окт. 21, 2022
Abstract
A
copper‐catalyzed
multicomponent
oxysulfonylation
of
alkenes
with
cyclobutanone
oxime
esters
and
hydroxamic
acids
via
the
insertion
sulfur
dioxide
has
been
developed.
This
reaction
uses
K
2
S
O
5
as
surrogate
in
situ
generated
amidoxyl
radical
interceptor,
thus
providing
a
direct
approach
to
β‐amidoxy
sulfones
35–90%
yields.
Mechanistic
studies
revealed
that
radical‐radical
coupling
alkyl
might
be
involved
this
transformation.
magnified
image
Organic Letters,
Год журнала:
2023,
Номер
25(38), С. 7062 - 7066
Опубликована: Сен. 19, 2023
A
visible-light-induced
radical
relay
strategy
to
access
heterocycles
bearing
a
monofluoromethylsufonyl
moiety
is
reported,
with
PhI(OCOCH2F)2
as
the
CH2F
precursor
and
DABSO
SO2
source.
range
of
oxindoles,
containing
CH2FSO2CH2–
group
at
C3
position,
were
synthesized
from
N-arylacrylamides
in
up
97%
yields.
The
protocol
features
catalyst-free
photochemical
tandem,
mild
reaction
conditions,
broad
functional
compatibility,
good
excellent
Advanced Synthesis & Catalysis,
Год журнала:
2024,
Номер
366(11), С. 2607 - 2612
Опубликована: Март 26, 2024
Abstract
Transition‐metal
catalyzed
difunctionalization
of
olefins
has
attracted
considerable
attention
as
a
method
to
construct
carbon‐carbon
and
carbon‐hetero
bonds.
Herein,
the
copper‐catalyzed
three‐component
radical
cross‐coupling
oxime
esters,
styrenes
AgSCF
3
through
visible‐light‐promoted
iminyl
radical‐mediated
bond
cleavage
strategy
been
described.
Utilizing
low‐cost
copper
salt
both
photosensitizers
cross‐couplers,
this
protocol
delivers
diverse
target
products,
providing
supplementary
approach
for
cyanoalkylation
trifluoromethylthiolation
drug
molecules.
