Chinese Journal of Chemistry,
Journal Year:
2022,
Volume and Issue:
40(17), P. 2040 - 2046
Published: June 4, 2022
Comprehensive
Summary
New
blue‐light
promoted
methods
for
the
addition
of
iodoacetonitrile
(ICH
2
CN)
to
alkene/alkynes
have
been
developed.
The
reaction
led
formation
cyanoalkylated
products
when
conjugated
alkene/styrene
was
used.
In
case
alkynes
and
non‐conjugated
alkenes,
iodoalkylation
takes
place
furnishing
corresponding
alkenyl
iodides
alkyl
iodides,
respectively.
Notably,
trans
‐alkenyl
were
obtained
as
major
product.
A
plausible
mechanism
is
also
proposed.
Nature Communications,
Journal Year:
2024,
Volume and Issue:
15(1)
Published: Feb. 17, 2024
Abstract
Transition
metal-catalyzed
reductive
difunctionalization
of
alkenes
with
alkyl
halides
is
a
powerful
method
for
upgrading
commodity
chemicals
into
densely
functionalized
molecules.
However,
super
stoichiometric
amounts
metal
reductant
and
the
requirement
installing
directing
group
to
suppress
inherent
β-H
elimination
bring
great
limitations
this
type
reaction.
We
demonstrate
herein
that
two
different
accessible
via
radical-anion
relay
Na
2
S
O
4
as
both
sulfone-source.
The
together
electron-shuttle
catalyst
crucial
divert
mechanistic
pathway
toward
formation
sulfone
anion
instead
previously
reported
alkylmetal
intermediates.
Mechanistic
studies
allow
identification
carbon-centered
radical
sulfur-centered
radical,
which
are
in
equilibrium
capture
or
extrusion
SO
could
be
converted
accelerated
by
iron
catalysis,
leading
observed
high
chemoselectivity.
ChemSusChem,
Journal Year:
2021,
Volume and Issue:
14(22), P. 4878 - 4902
Published: Sept. 3, 2021
Sulfones
play
a
pivotal
role
in
modern
organic
chemistry.
They
are
highly
versatile
building
blocks
and
find
various
applications
as
drugs,
agrochemicals,
or
functional
materials.
Therefore,
sustainable
access
to
this
class
of
molecules
is
great
interest.
Herein,
the
goal
was
provide
summary
on
recent
developments
field
sulfone
synthesis.
Advances
existing
limitations
traditional
approaches
towards
sulfones
were
reviewed
selected
examples.
Furthermore,
novel
emerging
technologies
for
more
synthesis
future
directions
discussed.
Organic Chemistry Frontiers,
Journal Year:
2022,
Volume and Issue:
9(4), P. 917 - 922
Published: Jan. 1, 2022
The
synthesis
of
β-azidosulfones
starting
from
alkenes,
cycloketone
oxime
esters,
trimethylsilyl
azide
and
a
sulfur
dioxide
surrogate
DABCO·(SO
2
)
under
iron
catalysis
is
developed.
Organic Letters,
Journal Year:
2020,
Volume and Issue:
22(7), P. 2639 - 2644
Published: March 18, 2020
A
visible-light-driven
photoredox-catalyzed
multicomponent
reaction
of
2-vinylanilines,
sulfonyl
chlorides,
and
sulfur
ylides
is
described.
This
protocol
features
redox-neutral
mild
conditions,
a
broad
substrate
scope,
good
functional
group
tolerance,
providing
access
to
various
sulfonated
2,3-disubstituted
indolines.
The
product
can
be
transformed
diverse
range
functionalized
indoles
by
selective
aromatization/nucleophilic
substitution
process.
Mechanistic
investigations
suggest
that
both
chlorides
serve
as
radical
sources,
the
proceeds
through
sequential
addition/addition/thermal
SN2-substitution
Organic Chemistry Frontiers,
Journal Year:
2022,
Volume and Issue:
9(7), P. 1937 - 1942
Published: Jan. 1, 2022
An
iron-catalyzed
dearomative
spirocyclization
of
biaryl
ynones
with
sodium
metabisulfite
and
cycloketone
oxime
esters
is
developed
for
the
construction
sulfonated
spiro[5,5]trienones.
Organic Chemistry Frontiers,
Journal Year:
2021,
Volume and Issue:
8(14), P. 3746 - 3751
Published: Jan. 1, 2021
A
photoredox-catalyzed
reaction
of
oximes,
rongalite
and
electrophiles
is
accomplished,
affording
pyrrole-substituted
aliphatic
sulfones
or
sulfonamides
in
moderate
to
good
yields.
The Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
89(7), P. 4877 - 4887
Published: March 8, 2024
General
and
convenient
visible-light-promoted
alkylsulfonylation
cyanoalkylsulfonylation
of
MBH
adducts
have
been
developed
through
the
multicomponent
insertion
sulfur
dioxide,
enabling
assembly
two
C–S
bonds
to
generate
structurally
diverse
allylic
alkylsulfones
(43
examples
in
total).
The
reaction
with
potassium
alkyltrifluoroborates
1,4-diazabicyclo[2.2.2]octane
bis(sulfur
dioxide)
adduct
afforded
sulfones
generally
good
yields.
Notably,
addition
N,N,N′,N′-tetramethylethylenediamine
as
a
base
into
photocatalytic
system
led
yielding
an
alkyl
sulfonyl
unit
cyano
group-anchored
trisubstituted
alkenes
by
utilizing
cycloketone
oxime
esters
C-radical
precursors.
Both
these
reactions
constructed
bonds,
all
desired
products
were
obtained
moderate
excellent
yields
complete
stereospecificity.
Organic Chemistry Frontiers,
Journal Year:
2021,
Volume and Issue:
8(21), P. 6119 - 6124
Published: Jan. 1, 2021
An
efficient
copper-catalyzed
multicomponent
reaction
of
1,6-enynes,
diselenides,
DABCO·(SO
2
)
,
and
cycloketone
oxime
esters
was
achieved,
providing
cyanoalkylsulfonated
pyrrolidines
in
moderate
to
good
yields.
