Molecules,
Год журнала:
2023,
Номер
28(23), С. 7869 - 7869
Опубликована: Ноя. 30, 2023
Both
sulfonyl
and
phosphorothioate
are
important
privileged
structural
motifs
which
widely
presented
in
pharmaceuticals
agrochemicals.
Herein,
we
describe
an
efficient
approach
to
synthesizing
sulfonyl-containing
phosphorothioates
by
merging
photoredox
copper
catalysis
at
room
temperature.
This
protocol
is
compatible
with
a
wide
range
of
substrates
can
be
applied
the
late-stage
modification
complex
molecules.
Control
experiments
conducted
demonstrate
generation
radical
transformation.
ACS Catalysis,
Год журнала:
2024,
Номер
14(5), С. 3664 - 3674
Опубликована: Фев. 21, 2024
Regioselective
1,2-dichalcogenation
of
alkenes
has
attracted
significant
attention
in
modern
organic
synthetic
chemistry.
While
there
are
a
plethora
methods
to
access
alkene
dichalcogenated
architectures,
sulfonylsulfination
is
extremely
challenging
due
the
inherent
characteristics
sulfur
atom.
Herein,
multicomponent
fragment
coupling
alkenes,
sulfinates,
and
DABSO
was
developed
construct
densely
functionalized
sulfonylsulfinated
products,
which
otherwise
access,
with
broad
substrate
scope
group
tolerance
under
mild
operationally
simple
conditions,
using
an
inexpensive
100–1000
ppm
photocatalyst.
In
addition,
protocol
applied
late-stage
functionalization
complex
molecules,
obtained
products
were
converted
into
diverse
downstream
transformations
demonstrate
their
potential.
Experimental
theoretical
mechanistic
investigations
suggest
that
these
reactions
proceed
through
sequential
sulfonyl
sulfinyl
oxygen
radical
mutual
radical–polar
crossover
coupling.
This
strategy
provides
previously
inaccessible
good-to-high
regio-
stereoselectivity,
along
opening
up
unexplored
directions.
Advanced Synthesis & Catalysis,
Год журнала:
2024,
Номер
366(10), С. 2352 - 2362
Опубликована: Апрель 5, 2024
Abstract
While
the
emergence
of
electrophotochemistry
provides
opportunities,
such
a
chemistry
at
this
stage
suffers
from
limited
reaction
types
and
high
photocatalyst
loadings.
A
self‐catalyzed
electrophotosynthesis
as
well
one
with
low
loading
is
presented.
These
external‐oxidant‐free
cyclizations
are
enabling
applicable
to
range
activated
alkenes,
affording
diverse
array
thiocyanato
heterocycles
including
4‐pyrrolin‐2‐ones,
isoquinoline‐1,3‐diones,
indolo[2,1‐
]isoquinolin‐6(5
H
)‐ones,
benzoimidazo[2,1‐
)‐ones
indolin‐2‐ones,
protocols
amenable
late‐stage
diversification
complex
molecular
architectures
gram‐scale
syntheses.
Sunlight
could
serve
light
source,
be
conducted
in
an
all‐solar‐driven
mode
using
commercially
available
photovoltaic
panel
produce
electricity.
European Journal of Organic Chemistry,
Год журнала:
2023,
Номер
26(25)
Опубликована: Апрель 25, 2023
Abstract
Compounds
containing
sulfonyl‐derived
functional
groups
have
received
intensive
attention
owing
to
their
widespread
applications
in
life
science,
pharmaceuticals
and
materials
science.
To
access
this
type
of
compounds,
the
multi‐component
sulfonylation
reactions
relying
on
sulfur
dioxide
(SO
2
)
insertion
strategy
emerged
as
novel
attractive
approaches
past
decade.
The
utilization
SO
surrogates
for
multicomponent
(MCRs)
improved
reaction
flexibility
step
economy.
Moreover,
some
advances
been
achieved
challenging
but
practical
asymmetric
MCRs
construction
high
value‐added
chiral
sulfones.
This
review
aims
summarize
progress
made
involving
from
2019
2022,
point
out
potentials
challenges
field.
Organic Letters,
Год журнала:
2023,
Номер
25(31), С. 5916 - 5921
Опубликована: Июль 27, 2023
A
copper-catalyzed
trifluoromethylthio-arylsulfonylation
between
1,3-enynes,
AgSCF3,
aryldiazonium
tetrafluoroborates,
and
SO2
(from
SOgen)
is
presented,
which
could
introduce
sulfone,
SCF3,
allene
moieties
into
one
molecule
simultaneously.
This
strategy
features
mild
reaction
conditions,
good
substrate
compatibility,
excellent
regioselectivity.
The
products
obtained
have
the
potential
for
further
conversion
other
valuable
compounds.
Initial
investigations
mechanism
suggest
that
it
may
proceed
via
a
radical
pathway.
Notably,
SOgen
was
proven
as
uniquely
effective
surrogate
in
this
transformation.
Organic Chemistry Frontiers,
Год журнала:
2024,
Номер
11(6), С. 1678 - 1684
Опубликована: Янв. 1, 2024
This
method
allows
for
the
enantioselective
synthesis
of
β-azide
sulfones
via
iron-catalyzed
vicinal
azide-sulfonylation
acrylamides.
It
makes
first
instance
achieving
asymmetric
construction
through
iron
catalysis
with
SO
2
insertion.
Organic Letters,
Год журнала:
2024,
Номер
26(40), С. 8447 - 8452
Опубликована: Авг. 22, 2024
Owing
to
their
diverse
biological
activities
and
versatility
as
synthetic
precursors,
organoselonocyanes
categorize
themselves
vital
compounds.
However,
a
limited
reagent
pool
restricts
utility.
In
the
present
work,
alkyl
selenocyanates
are
hereby
established
new
bifunctional
reagents
for
simultaneous
transfer
of
an
group
in
addition
−SeCN.
These
reagents,
when
merged
with
photocatalysis,
provide
key
accessing
organoselenocyanates
from
feedstock
olefins
efficient
atom-economic
fashion.
A
route
analogous
isoselenocyanate
isomers
facilitated
by
Lewis
acid
catalysis
is
also
reported,
presenting
divergent
strategy
both
ambident
−SeCN
manner.
Organic Letters,
Год журнала:
2023,
Номер
25(50), С. 9047 - 9052
Опубликована: Дек. 12, 2023
Activated
by
visible
light,
arylazo
sulfones
can
serve
as
multifaceted
reactants
and
are
employed
in
diazenylation,
sulfonylation,
arylation
reactions
under
(photo)catalyst-free
conditions.
Such
versatile
reactivity
enabled
us
to
develop
an
operationally
simple,
regioselective,
tunable
difunctionalization
of
styrenes
with
produce
α-sulfonyl
arylhydrazones
1,2-alkoxyarylated
products
moderate
excellent
yields.
Furthermore,
such
difunctionalized
have
been
exploited
key
building
blocks
for
the
synthesis
various
heterocycles.
Organic Chemistry Frontiers,
Год журнала:
2024,
Номер
11(7), С. 1975 - 1981
Опубликована: Янв. 1, 2024
A
novel
alkyl
radical-initiated
alkylsulfonylation
of
alkenes
involving
copper
carbene
coupling
is
developed
for
the
synthesis
various
alkyl–alkyl
sulfones
by
employing
potassium
metabisulphite
(K
2
S
O
5
)
as
a
connector.
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.
The
conjugate
additions
of
nucleophiles
to
acceptors
are
among
the
most
powerful
hetero-carbon
bond
formation
reactions.
addition
normally
occurs
via
a
β-nucleophilic
addition,
resulting
in
stabilized
α-carbanion
intermediate
that
can
be
subsequently
quenched
by
electrophiles
or
protons.
Nevertheless,
inverse
involving
an
α-specific
nucleophilic
remains
less
explored
because
electronic
mismatch.
In
this
research,
we
disclosed
including
Py·HF,
TBACl,
HOR,
H
2
O,
18
RCO
H,
and
pyrazole
concurrent
with
trifluoromethylation.
This
umpolung
inversely
regioselective
enabled
visible
light–induced
redox
photocatalysis,
occurred
unusual
α-nucleophilic
other
than
normal
efficiently
generate
diverse
α-functionalized
CF
3
-containing
amides/esters.
broad
substrate
scope,
excellent
functional-group
tolerance,
versatile
late-stage
derivatizations
as
well
biologically
functionally
important
products
demonstrated
potential
applications
protocol
materials,
agrochemicals,
pharmaceutical
chemistry.
