Organic & Biomolecular Chemistry,
Journal Year:
2023,
Volume and Issue:
21(39), P. 7895 - 7899
Published: Jan. 1, 2023
Aminophenols
are
a
class
of
important
compounds
with
various
pharmacological
activities
such
as
anticancer,
anti-inflammatory,
antimalarial,
and
antibacterial
activities.
Herein,
we
introduce
mild
efficient
electrochemical
selenium-catalyzed
strategy
to
synthesize
polysubstituted
aminophenols.
High
atom
efficiency
transition
metal-free
oxidant-free
conditions
the
striking
features
this
protocol.
By
merging
organoselenium-catalyzed
processes,
intramolecular
rearrangement
N-aryloxyamides
produces
para-amination
products
at
room
temperature
in
simple
undivided
cell.
Synthesis,
Journal Year:
2023,
Volume and Issue:
56(15), P. 2295 - 2315
Published: Oct. 24, 2023
Abstract
In
this
article
we
have
focused
on
the
use
of
selenium
in
catalysis
along
with
proposed
reaction
mechanisms.
With
increasing
interest
chemistry,
highlighted
most
significant
features
subject,
mainly
last
years.
Selenium-containing
catalysts
a
key
role
many
transformations;
for
example,
oxidation
reactions
that
are
performed
under
very
mild
and
controlled
conditions.
addition,
utilizing
weak
selenium–oxygen
bonding
interaction
has
proved
to
be
useful
as
catalytic
approach
specific
transformations.
The
cycles
each
appropriate
transformation
fully
reviewed.
1
Introduction
2
Use
Selenium
Catalysis:
Perspectives
2.1
Directing
Group:
Preparation
Organoselenium
Compounds
via
C–H
Borylation
2.2
Multicomponent
Reactions
Employing
Catalyst
2.3
Selenium-π-Acid
Catalysts
2.4
Electrochemical
Selenium-Catalyzed
2.5
Stereoselective
Synthesis
2.6
Transition-Metal
Containing
Selenium-Based
Ligands
2.6.1
Selenium-Ligated
Palladium(II)
Complexes
Heck
Reaction
2.6.2
Pincer
Allylation
Aldehydes
Closely
Related
Functional
Groups
2.6.3
Employed
Buchwald-Type
C–N
Coupling
2.6.4
Suzuki–Miyaura
2.7
Catalysis
Michael-Type
2.8
Catalytic
Cycle
Glutathione
Peroxidase
2.9
Epoxidation
2.10
Dihydroxylation
2.11
Oxidation
2.12
Bromolactonization
2.13
Alkenes
from
Vicinal
Diols
2.14
α-Selanyl
Enals
Propargylic
Alcohols
2.15
Miscellanea
3
Concluding
Remarks
Asian Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
12(8)
Published: June 27, 2023
Abstract
A
green
electrochemical
C(sp
2
)−H
trifluoromethylation
of
imidazo[1,2‐
a
]pyridines
by
engaging
Langlois’
reagent
is
reported.
This
oxidative
regioselective
CF
3
‐functionalization
strategy
operates
under
open
atmosphere,
in
an
undivided
cell
and
at
ambient
temperature.
Regioselective
C−CF
bond
formation
was
achieved
exclusively
applying
this
mild
protocol
exhibiting
broad
functional
group
compatibility
affording
the
desired
product
up
to
79%
isolated
yield.
Mechanistic
studies
indicated
radical
pathway
for
redox
transformation.
Organic Letters,
Journal Year:
2023,
Volume and Issue:
25(41), P. 7578 - 7583
Published: Oct. 9, 2023
Synthesis
of
unsymmetrical
but-2-yne-1,4-diones
is
reported
through
oxidative
alkyne
translocation
readily
accessible
homopropargylic
alcohols.
The
developed
method
consists
an
unprecedented
one-pot
sequential
electro-oxidative
annulation-fragmentation-chemical
selenoxide
elimination
process.
Excellent
functional
group
compatibility
was
observed,
and
array
yne-1,4-diones
were
synthesized.
Derivatization
the
gave
access
to
other
valuable
scaffolds.
Detailed
mechanistic
studies
isolation
key
intermediates
clarified
cascade
transformation.
The Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
88(21), P. 15414 - 15427
Published: Oct. 23, 2023
Unprecedented
regioselective
electrochemical
tandem
selenation/cyclization
of
alkynyl
phosphonates
with
diselenide
is
described
here.
These
obtained
selenoether
products
can
be
chemo-selectively
converted
into
halogen-functionalized
cyclic
enol
under
our
conditions.
protocols
provide
straightforward
access
to
valuable
phosphonate
or
phosphaisocoumarins
the
and
transition-metal-free
The
robustness
these
transformations
was
illustrated
by
their
compatibility
various
complex
natural
bioactive
molecules.
halogen
functional
groups
allow
further
diversification
phosphorus
heterocycles
thus
obtained.
Abstract
Electrosynthesis
of
selenylated‐oxazolone
derivatives
via
cascade
selenylation/cyclization
ynamides
was
disclosed.
A
series
diaryl
diselenides,
dialkyl
and
heteroaryl‐substituted
tolerated
in
this
protocol
delivered
4‐selenyloxazolones
28–83%
yields.
The
scale‐up
reaction
the
oxidation
performed
to
showcase
practicability
method.
Furthermore,
mechanistic
experiments
indicated
that
a
cationic
pathway
instead
radical
probably
involved.
Angewandte Chemie,
Journal Year:
2023,
Volume and Issue:
135(36)
Published: July 17, 2023
Abstract
Despite
their
abundance
in
organic
molecules,
considerable
limitations
still
exist
synthetic
methods
that
target
the
direct
C−H
functionalization
at
sp
3
‐hybridized
carbon
atoms.
This
is
even
more
case
for
light
alkanes,
which
bear
some
of
strongest
bonds
known
Nature,
requiring
extreme
activation
conditions
are
not
tolerant
to
most
molecules.
To
bypass
these
issues,
chemists
rely
on
prefunctionalized
alkyl
halides
or
organometallic
coupling
partners.
However,
new
regioselectively
a
variety
different
scaffolds
would
be
great
added
value,
only
late‐stage
biologically
active
molecules
but
also
catalytic
upgrading
cheap
and
abundant
hydrocarbon
feedstocks.
Here,
we
describe
general,
mild
scalable
protocol
enables
C(sp
)−H
carbonylation
saturated
hydrocarbons,
including
natural
products
using
photocatalytic
hydrogen
atom
transfer
(HAT)
gaseous
monoxide
(CO).
Flow
technology
was
deemed
crucial
enable
high
gas‐liquid
mass
rates
fast
reaction
kinetics,
needed
outpace
deleterious
pathways,
leverage
safe
process.
SynOpen,
Journal Year:
2023,
Volume and Issue:
07(04), P. 521 - 534
Published: Sept. 6, 2023
Abstract
Organoselenium
compounds
are
crucial
molecules
that
utilized
extensively
in
diverse
fields
such
as
medicine,
agriculture,
catalysis,
and
organic
materials.
The
incorporation
of
selenium
atoms
into
holds
significant
importance
synthetic
chemistry.
Organic
electrochemical
synthesis,
a
green,
mild,
efficient
strategy,
has
displayed
remarkable
potential
for
organoselenium
chemistry
synthesis.
Consequently,
there
been
substantial
interest
recent
years
researching
electrochemically
mediated
synthesis
compounds.
This
review
provides
an
overview
the
progress
made
reactions
over
last
decade,
including
oxidation
diselenide
coupling,
tandem
selenocyclization.
scope,
limitations,
mechanisms
those
emphasized.
1
Introduction
2
Electrochemical
Selenium-Catalyzed
Reactions
3
Electrochemically
Mediated
Coupling
Aromatic/Heterocyclic
Rings
with
Diselenides
4
Tandem
Selenocyclization
5
Conclusion
Green Synthesis and Catalysis,
Journal Year:
2024,
Volume and Issue:
unknown
Published: Jan. 1, 2024
A
selenium-catalyzed
electrosynthesis
involving
regio-
and
stereo-selective
N-olefination
of
azoles
was
developed.
The
room-temperature
reaction
efficient
(up
to
97%
yield)
compatible
with
various
styrenes
azoles.
Mechanistic
study
showed
that
the
cascade
triggered
by
selenium-cation-mediated
electrophilic
trans-aminoselenation,
followed
an
oxidative
cis-elimination
selane.
also
well
more
challenging
internal
alkene
substrates,
giving
desired
N-vinyl
in
up
88%
yield
>
20:1
Z/E
ratio.
Organic & Biomolecular Chemistry,
Journal Year:
2023,
Volume and Issue:
21(39), P. 7895 - 7899
Published: Jan. 1, 2023
Aminophenols
are
a
class
of
important
compounds
with
various
pharmacological
activities
such
as
anticancer,
anti-inflammatory,
antimalarial,
and
antibacterial
activities.
Herein,
we
introduce
mild
efficient
electrochemical
selenium-catalyzed
strategy
to
synthesize
polysubstituted
aminophenols.
High
atom
efficiency
transition
metal-free
oxidant-free
conditions
the
striking
features
this
protocol.
By
merging
organoselenium-catalyzed
processes,
intramolecular
rearrangement
N-aryloxyamides
produces
para-amination
products
at
room
temperature
in
simple
undivided
cell.
