A
simple
yet
efficient
approach
towards
the
synthesis
of
β-hydroxy
selenylated
ketones
was
developed
from
easily
accessible
chalcones
and
diphenyl
diselenide
through
an
electrochemical
pathway.
In
this
technique,
water
are
source
PhSe.
hydroxyl
(-OH)
groups
that
can
be
inserted
at
α
β
positions
respectively
producing
in
moderate
to
good
yields.
The
reaction
features
difunctionalization
ketones,
catalyst
free,
mild
conditions,
stereo
regioselectivity
undivided
cell
room
temperature.
For
transformation,
a
plausible
radical
mechanism
has
been
put
out.
Organic & Biomolecular Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Янв. 1, 2025
Selenium-based
catalysts
have
recently
been
utilized
to
facilitate
a
variety
of
new
organic
transformations,
owing
their
intrinsic
advantages,
including
low
cost,
toxicity,
stability
in
both
air
and
water,
strong
compatibility
with
diverse
functional
groups.
The
difunctionalization
alkenes-the
process
incorporating
two
groups
onto
carbon-carbon
double
bond-has
garnered
particular
interest
within
the
chemical
community
its
significant
applications
synthesis.
Recently,
organoselenium-catalyzed
alkenes
has
emerged
as
an
ideal
powerful
route
obtain
high-value
vicinal
difunctionalized
molecules.
This
review
emphasizes
recent
advancements
this
rapidly
evolving
field,
focusing
on
scope,
limitations,
mechanisms
various
reactions.
The Journal of Organic Chemistry,
Год журнала:
2023,
Номер
88(11), С. 7431 - 7447
Опубликована: Май 23, 2023
Three-component
selenofunctionalization
processes
of
olefins,
diselenides
and
sulfonamides,
water,
alcohols,
or
acids
utilizing
1-fluoropyridinium
triflate
(FP-OTf)
as
a
reaction
promoter
are
reported.
Under
the
optimal
conditions,
broad
range
vicinally
functionalized
selenide
derivatives
was
accessible
with
high
yields
excellent
functional
group
compatibilities.
Mechanistic
studies
revealed
that
FP-OTf
played
key
role
in
this
process.
Advanced Synthesis & Catalysis,
Год журнала:
2023,
Номер
365(14), С. 2310 - 2331
Опубликована: Июнь 24, 2023
Abstract
Alkenes
are
valuable
feedstocks
in
organic
synthesis.
Selenium
or
sulfur‐containing
coumpounds
with
a
neighboring
functional
group
can
be
easily
prepared
by
direct
difunctionalization
of
alkenes
via
three‐component
reactions.
It
will
reduce
the
number
steps
and
waste
generation,
form
complicated
molecules
from
simple
starting
materials.
Herein,
recent
developments
(2013–2022)
have
been
summarized
two
categories:
(1)
selenylation
seleniranium
intermediates
Se‐centered
radicals;
(2)
thiolation
more
diverse
mechanisms
products
Reactions
electron‐rich
arenes,
alcohols,
water,
acids,
NaN
3
,
amines,
KSCN,
sulfamides,
TMSNCS,
TMSN
Et
N
⋅
3HF,
SOCl
2
HCl,
NFSI,
t
BuONO,
pyridinium
salts,
BuOOH,
ArN
BF
4
CO
CO,
O
CF
SO
Cl,
R
P(O)−H,
(RO)
P(O)SH,
P(O)OH
et
al
discussed.
We
hope
this
review
do
help
for
future
research
area.
Chemistry - A European Journal,
Год журнала:
2024,
Номер
30(36)
Опубликована: Апрель 23, 2024
Three
hybrid
electrochemical
protocols,
which
involve
the
energy
transfer,
direct
photolysis
and
N-hydroxyphthalimide
catalyst,
respectively,
are
presented
for
selenylation/cyclization
of
fragile
substrates
3-aza-1,5-dienes
with
diorganyl
diselenides
to
afford
3-selenomethyl-4-pyrrolin-2-ones.
The
two
electrophotocatalytic
reactions
indirect
electrolysis
one
both
regioselective
external-oxidant-
transition-metal-free,
associated
a
broad
substrate
scope
high
Se-economy,
all
three
methods
amenable
gram-scale
syntheses,
late-stage
functionalizations,
sunlight-induced
experiments
all-solar-driven
syntheses.
Abstract
A
practical
electrochemical
method
for
the
synthesis
of
β‐hydroxyselenides
has
been
developed
under
an
external
oxidant‐free
condition
at
room
temperature
air
from
alkenes
with
diselenides
and
H
2
O.
radical
mechanism
is
proposed
this
transformation
gram‐scale
reactions
demonstrate
practicability
reaction.
Chemistry - A European Journal,
Год журнала:
2023,
Номер
29(35)
Опубликована: Март 15, 2023
A
dual
catalytic
approach
combining
photocatalyst
and
selenium-π-acid
synergy
has
been
used
to
cyclized
of
N-propargylamides.
This
method
offers
readily
access
oxazole
aldehydes
under
chemical
oxidant-free
conditions
with
low
catalyst
loadings,
where
air
acts
as
a
terminal
gratuitous
oxidant.
The
reaction
is
demonstrated
range
substrates,
including
aryl
alkyl
propargyl
amides,
in
the
late-stage
functionalization
several
amide-containing
drug
molecules.
Mechanistic
studies
suggest
that
acridinium
able
oxidize
diselenide
generate
singlet
oxygen
(1
O2
),
which
responsible
for
this
transformation.
