European Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
27(46)
Published: Aug. 28, 2024
Abstract
Alkynes
are
valuable
building
blocks
in
organic
synthesis.
They
can
undergo
three‐component
difunctionalization
to
create
sulfur
or
selenium‐containing
compounds.
Three‐component
reactions
of
alkynes
atom
economic,
practical
and
regioselective.
This
review
will
disscuss
decade
developments,
including
C−S
C−Se
bond
formation
via
thiolation,
sulfonylation
selenylation.
Recent
developments
be
mainly
categorized
into
three
types.
(1)
Radical
C−S/S−Se
is
a
hot
topic.
Reactions
initiated
by
S/Se
radicals
other
exhibit
two
types
selectivities.
Photochemical
electrochemical
under
eco‐friendly
conditions
have
been
increasingly
reported.
(2)
Some
transformations
involve
electrophilic
three‐membered
ring
intermediates.
Thiiraniums,
seleniraniums,
iodoniums
among
the
most
prevalent
species.
ring‐opening
various
nucleophiles
participate
tandem
reactions.
(3)
Metal‐catalyzed
reactions,
classic
category,
also
discussed
text.
In
following
section,
we
provide
an
overview
based
on
mechanisms
substrates.
The
roles
added
reagents
discussed.
Organic Chemistry Frontiers,
Journal Year:
2023,
Volume and Issue:
11(2), P. 597 - 630
Published: Nov. 23, 2023
This
review
highlights
the
recent
progress
in
electrochemical
difunctionalization
of
alkenes
and
alkynes
involving
C–S/Se
bond
formation
to
access
organochalcogen
frameworks.
The Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
89(6), P. 4074 - 4084
Published: Feb. 23, 2024
Herein,
an
oxidant-
and
metal-free
electrochemical
selenylation
reaction
of
chalcones
with
diselenides
for
the
synthesis
3-selenylazaflavanones
3-selenylflavanones
at
room
temperature
was
reported.
The
method
proceeded
under
mild
conditions,
exhibited
a
broad
substrate
scope,
provided
selenylated
products
in
moderate
to
excellent
yields
high
regio-
stereoselectivity.
could
also
be
readily
scaled
up
efficiency.
Detailed
mechanistic
studies
through
control
experiments
disclosed
that
selenium-based
radical
might
participate
this
transformation.
Organic & Biomolecular Chemistry,
Journal Year:
2024,
Volume and Issue:
22(9), P. 1775 - 1781
Published: Jan. 1, 2024
This
work
demonstrates
the
electrochemical
construction
of
2-methyl-1-aryloxy-3-(arylselanyl)propan-2-ol/2-hydroxy-2-methyl-3-(arylselanyl)propyl
2-(2-hydroxy-2-methyl-3-(arylselanyl)propoxy)benzoate
starting
from
aryl
allyl
ethers/allyl
benzoates
and
diaryl
diselenides
under
additive-free
conditions.
environmentally
friendly
method
was
achieved
through
constant
current
electrolysis
in
an
undivided
cell
setup
acid,
oxidant,
or
catalyst-free
Additionally,
this
technique
enabled
synthesis
a
variety
β-hydroxy
selenides
including
late-stage
functionalization
drug
derivatives
good
to
exceptional
yields
across
various
substrates
mild
reaction
Organic & Biomolecular Chemistry,
Journal Year:
2024,
Volume and Issue:
22(30), P. 6198 - 6204
Published: Jan. 1, 2024
Reported
herein
is
a
visible-light
induced
selenocyclization
of
2-ethynylanilines
under
ambient
conditions,
with
simple
FeBr
3
as
dual-functional
catalyst.
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.
Chemical Communications,
Journal Year:
2025,
Volume and Issue:
unknown
Published: Jan. 1, 2025
In
this
study,
a
straightforward
and
environmentally
benign
electrochemical
mono-functionalization
of
alkenes
has
been
established
for
the
synthesis
alkenyl
selenium
sulfonates
using
elemental
as
source.
Chemistry - A European Journal,
Journal Year:
2024,
Volume and Issue:
30(36)
Published: April 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.
Chinese Journal of Chemistry,
Journal Year:
2024,
Volume and Issue:
42(14), P. 1623 - 1629
Published: March 15, 2024
Comprehensive
Summary
Lewis
base
catalyzed
and
Brønsted
acid
controlled
chemodivergent
electrophilic
selenofunctionalizations
of
alkynes
were
developed
for
the
first
time.
Various
selenium‐containing
tetrasubstituted
alkenes
readily
obtained
in
moderate
to
excellent
yields
with
complete
E
/
Z
selectivities.
As
substrates
1‐ethynyl
naphthol
derivatives,
linear
produced
via
intermolecular
oxygen
nucleophilic
attack
absence
additive;
contrast,
cyclic
generated
through
intramolecular
carbon
capture
addition
acid.
Chemical Communications,
Journal Year:
2024,
Volume and Issue:
60(55), P. 7057 - 7060
Published: Jan. 1, 2024
A
metal-
and
oxidant-free,
electricity-driven
C–H
selenylative
tellurylative
annulation
of
N
-(2-alkynyl)anilines
with
diorganyl
dichalcogenides
is
developed
to
access
3-chalcogenylquinolines.
Organic & Biomolecular Chemistry,
Journal Year:
2023,
Volume and Issue:
22(4), P. 645 - 681
Published: Dec. 23, 2023
Organochalcogen
compounds
are
prevalent
in
numerous
natural
products,
pharmaceuticals,
agrochemicals,
polymers,
biological
molecules
and
synthetic
intermediates.
Direct
chalcogenation
of
C-H
bonds
has
evolved
as
a
step-
atom-economical
method
for
the
synthesis
chalcogen-bearing
compounds.
Nevertheless,
direct
severely
lags
behind
C-C,
C-N
C-O
bond
formations.
Moreover,
compared
with
monochalcogenation,
reports
selective
mono-/dichalcogenation
exclusive
dichalcogenation
relatively
scarce.
The
past
decade
witnessed
significant
advancements
various
C(sp
