Organic & Biomolecular Chemistry,
Год журнала:
2023,
Номер
21(39), С. 7895 - 7899
Опубликована: Янв. 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.
Angewandte Chemie International Edition,
Год журнала:
2023,
Номер
62(36)
Опубликована: Июль 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.
Organic Chemistry Frontiers,
Год журнала:
2023,
Номер
11(2), С. 597 - 630
Опубликована: Ноя. 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.
Organic Letters,
Год журнала:
2023,
Номер
25(20), С. 3812 - 3817
Опубликована: Май 17, 2023
Intramolecular
electro-oxidative
addition
of
enamines
or
amides
to
nonactivated
alkynes
was
attained
access
carbonyl-pyrroles
-oxazoles
from
N-propargyl
derivatives.
Organoselenium
employed
as
the
electrocatalyst,
which
played
a
crucial
role
π-Lewis
acid
and
selectively
activated
alkyne
for
successful
nucleophilic
addition.
The
synthetic
strategy
permits
wide
range
substrate
scope
up
93%
yield.
Several
mechanistic
experiments,
including
isolation
selenium-incorporated
intermediate
adduct,
enlighten
electrocatalytic
pathway.
Organic & Biomolecular Chemistry,
Год журнала:
2022,
Номер
20(43), С. 8501 - 8505
Опубликована: Янв. 1, 2022
The
first
example
of
the
electrocatalytic
multicomponent
synthesis
4-chloro/bromo/iodopyrazoles
from
hydrazines,
acetylacetones
and
sodium
halides
under
chemical
oxidant-
external
electrolyte-free
conditions
has
been
developed.
Organic Letters,
Год журнала:
2022,
Номер
24(51), С. 9419 - 9424
Опубликована: Дек. 21, 2022
A
green
and
efficient
approach
for
the
difunctionalization
of
ynamides
by
merging
electrochemical
organoselenium-catalyzed
processes
is
described.
This
strategy
features
mild
reaction
conditions,
broad
functional
group
tolerance
high
atom-economy,
requires
no
external
chemical
oxidant.
Hence,
we
provide
a
sustainable
alternative
synthesis
polysubstituted
oxazoles.
Advanced Synthesis & Catalysis,
Год журнала:
2024,
Номер
366(11), С. 2544 - 2550
Опубликована: Апрель 5, 2024
Abstract
We
have
developed
an
approach
for
the
construction
of
naphthofuran‐2‐carboxaldehyde
derivatives
utilizing
synergy
electrochemical
oxidation
and
organo‐selenium
catalysis
at
room
temperature.
The
compatibility
various
functional
groups
scalability
this
protocol
demonstrate
practicality
strategy.
synthetic
utility
strategy
is
furthermore
demonstrated
by
synthesizing
diversified
molecules
through
downstream
transformations.
Organic Letters,
Год журнала:
2025,
Номер
27(4), С. 961 - 966
Опубликована: Янв. 21, 2025
An
electrochemical
strategy
for
the
regioselective
construction
of
seleno-benzothiophenes/furans
is
reported
through
selenocyclization,
followed
by
Wagner-Meerwein
rearrangement.
This
electro-oxidative
tandem
process
operates
under
metal-free
and
external
chemical
oxidant-free
conditions.
Advantageously,
unprotected
homopropargyl
alcohols
were
found
to
be
compatible
reaction
conditions,
releasing
water
dihydrogen
as
biproduct.
methodology
reveals
good
functional
group
tolerance,
allowing
a
broad
spectrum
substrate
scopes
up
87%
isolated
yield.
The Journal of Organic Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Фев. 7, 2025
A
transition-metal-free
electrochemical
chalcogenative
cyclization
of
2-alkynyl
aryl
oxime
with
dichalcogenides
has
been
established
to
assemble
valuable
4-organochalcogen
isoquinolines
concisely.
This
protocol
proceeds
via
constant
electrolysis
in
a
user-friendly
undivided
cell
setup.
It
circumvents
the
necessity
transition
metal
catalysts,
chemical
oxidants,
and
harsh
reaction
conditions.
The
practical
utilities
current
were
illustrated
by
excellent
functional
group
tolerance,
remarkable
regio-selectivity,
easy
scalability,
mild
conditions,
transformable
isoquinoline
products.
ACS Catalysis,
Год журнала:
2023,
Номер
13(15), С. 10115 - 10136
Опубликована: Июль 19, 2023
Water
addition
on
an
unsymmetrical
internal
alkyne
has
significance
in
organic
chemistry
and
stimulated
challenging
approaches
to
access
a
highly
regioselective
process.
Hydration
or
formal
hydration
is
presented
according
the
type
of
alkyne.
Methods
for
electron-rich
-poor
diarylalkynes
followed
by
those
adapted
arylalkylalkynes
are
presented.
Regioselective
reactions
propargylic
homopropargylic
derivatives
then
discussed,
aspects
alkynes
directed
carbonyl
groups.
The
following
section
examines
linked
CF3,
esters,
ketones,
heteroatoms
as
haloalkynes,
alkynylphosphonates,
ynamides,
others.
At
end
this
section,
we
report
some
recent
examples
where
triple
bond
connected
electron-withdrawing
group
ester
ketone.
Reactions
presented,
illustrated
each
these
items
through
various
representative
examples.
mechanistic
hypotheses
explaining
origin
regioselectivity
discussed.
This
review
advances
(from
2007
until
present)
aims
update
current
body
knowledge
aid
researchers
working
field.
