European Journal of Organic Chemistry,
Год журнала:
2022,
Номер
2022(48)
Опубликована: Дек. 5, 2022
Abstract
A
simple,
metal‐free,
and
green
approach
has
been
established
for
N−H
functionalization
of
sulfoximines
under
mild
reaction
conditions
to
offer
sulfoximinated‐oxime
conjugates.
The
works
well
in
EtOH
at
room
temperature
proceeds
smoothly
without
using
any
base
or
expensive
ligands.
This
protocol
applied
on
various
aryl‐,
heteroaryl‐
as
variety
chloro‐oximes.
Both
the
substrates
tolerated
a
wide
range
functional
groups,
resulting
good
excellent
yields.
It
can
serve
directing
group
organic
synthesis,
precursor
building
block,
demonstrating
product's
applicability
importance
field.
applications
have
demonstrated
sulfoximination
some
natural
products.
strategy
could
be
useful
drug
discovery
medicinal
chemistry
fine‐tuning
physicochemical
properties
product
scaffolds
lead
candidates.
European Journal of Organic Chemistry,
Год журнала:
2024,
Номер
27(27)
Опубликована: Май 21, 2024
Abstract
The
direct
functionalization
of
quinones
has
always
fascinated
research
communities
due
to
their
biological
and
redox
activities
subsequent
application.
Quinone
motifs
play
a
vital
role
as
precursors
for
many
bioactive
compounds
materials;
hence,
ingenious
methodologies
have
been
elaborated
exploring
these
units.
A
significant
part
the
synthetic
strategies
towards
functionalized
achieved
by
installing
substituents
on
hydroquinones,
phenols,
or
quinone
itself
different
oxidative
coupling
reactions
via
radical
pathways
with
without
utilization
metal
catalysts.
simple
C−H
bond
remains
challenging
inherited
electronic
nature
high
dissociation
energy.
This
review
article
summarizes
recent
advancement
made
through
quinones.
Our
primary
focus
will
be
approaches
mechanistic
that
appeared
in
last
two
decades,
along
short
historical
importance
family.
Organic Chemistry Frontiers,
Год журнала:
2024,
Номер
11(8), С. 2195 - 2200
Опубликована: Янв. 1, 2024
A
Heck-like
coupling
of
cyclic
sulfonium
salts
with
alkenes
via
selective
C–S
bond
cleavage
using
a
copper
complex
as
photosensitizer
through
visible-light-driven
redox-neutral
process
has
been
developed.
The Journal of Organic Chemistry,
Год журнала:
2023,
Номер
88(11), С. 7401 - 7424
Опубликована: Май 12, 2023
Herein,
we
report
a
blue-light-driven
amination
of
C(sp2)-H
bond
naphthoquinones
and
quinones
with
the
N-H
primary
secondary
amines
for
synthesis
2-amino-naphthoquinones
2-amino-quinones.
The
coupling
wide
array
aliphatic,
aromatic,
chiral,
primary,
having
electron
donating
(-CH3,
-OCH3,
-SCH3),
withdrawing
(-F,
-Cl,
-Br,
-I),
CO2H,
-OH,
-NH2
groups
acidic
protons
selectively
occurred
to
afford
C-N
coupled
in
60-99%
yields
hydrogen
gas
as
byproduct
methanol
solvent
without
using
any
additional
reagents,
additives,
oxidant
under
blue
light
irradiation.
Mechanistic
insight
by
DFT
computation,
controlled
experiments,
kinetic
isotopic
effect,
substitution
effect
substrates
suggest
that
reaction
proceeds
radical
pathway
which
naphthoquinone
forms
highly
oxidizing
naphthoquinonyl
biradical
upon
irradiation
(457
nm).
Consequently,
transfer
from
electron-rich
amine
an
leads
anion
aminyl
cation,
followed
proton
delocalization
leading
carbon-centered
radical.
cross-coupling
nitrogen
radicals
bond,
subsequent
elimination
(which
was
also
confirmed
GC-TCD),
affording
2-amino-1,4-naphthoquinone
metal-,
reagent-,
base-,
oxidant-free
conditions.
Green Chemistry,
Год журнала:
2023,
Номер
25(21), С. 8838 - 8844
Опубликована: Янв. 1, 2023
We
describe
an
electrochemical
N
-acylation
and
-α-ketoacylation
of
sulfoximines
via
the
selective
decarboxylation
dehydration
α-ketoacids
using
electricity
as
a
“traceless”
oxidant
α-ketoacid
“acyl”
or
“α-ketoacyl”
source.
ACS Materials Letters,
Год журнала:
2023,
Номер
6(1), С. 212 - 221
Опубликована: Дек. 14, 2023
Vinylene-linked
covalent
organic
frameworks
(COFs)
are
considered
promising
heterogeneous
photocatalyst
candidates
for
synthesis
because
of
their
robust
and
conjugated
frameworks.
For
the
first
time,
a
series
vinylene-linked
COFs
decorated
by
halogen
atoms
(F,
Cl,
Br)
were
synthesized
further
utilized
as
photocatalysts
C–H
activation
reactions.
The
corresponding
optoelectronic
properties
could
be
precisely
regulated
via
modulation
functionalities
in
nanopore
channel
COFs.
It
is
worth
noting
that
unique
structures
make
these
effective
reactions
synthesis.
All
exhibited
extraordinary
catalytic
performance
reusability
functionalization
based
on
functionalities.
Especially,
highest
yield
was
achieved
photocatalytic
thiolation
1,4-naphthoquinones
with
Br-COF
suitable
conduction
band
position.
This
work
may
provide
new
scaffold
to
rationally
design
efficient
Chinese Journal of Organic Chemistry,
Год журнала:
2023,
Номер
43(4), С. 1386 - 1386
Опубликована: Янв. 1, 2023
In
recent
years,
the
development
and
application
of
transition
metal
ruthenium
or
iridium
complexes
based
photocatalysts
have
opened
up
a
new
research
field
for
organic
synthesis,
which
provides
mild
efficient
strategies
construction
chemical
bonds
transformations.In
order
to
enrich
types
photocatalysts,
broaden
scope
photocatalysis,
develop
green
sustainable
chemistry,
some
low-cost
easily
available
organometallic
with
copper
iron
were
applied
as
recently.Iron-complexes
feature
non-toxicity,
rich
variety,
unique
property
charge
transfer
from
ligands
metals,
enable
them
show
extraordinary
capability
in
photocatalytic
synthesis.According
different
reaction
types,
this
review
focuses
on
photoinduced
iron-catalysis
synthesis
including
C-H
bond
functionalization,
C-C
bifunctionalization
alkenes,
cross-coupling
reaction,
decarboxylative
selective
oxidation
reduction.
Organic & Biomolecular Chemistry,
Год журнала:
2024,
Номер
unknown
Опубликована: Янв. 1, 2024
The
combination
of
benzylamine,
potassium
tert
-butoxide
and
18-crown-6
acts
as
an
excellent
catalytic
medium
for
the
C–H
arylation
arenes
or
heteroarenes
with
aryl
heteroaryl
iodides/bromides
under
heating
light
irradiation.
Chemical Communications,
Год журнала:
2024,
Номер
unknown
Опубликована: Дек. 23, 2024
Due
to
the
special
structure
and
physicochemical
properties
of
sulfoximines,
research
on
sulfoximines
has
achieved
great
progress
in
recent
decades,
especially
chemical
medicinal
fields.
This
review
highlights
advancements
N-functionalization
NH-sulfoximines,
focusing
classical
cross-coupling
reactions
with
electrophilic
agents
oxidative
coupling
extensive
organic
compounds,
including
specific
(hetero)arenes,
alkenes
(1,4-naphthoquinones),
alkanes
(cyclohexanes),
nucleophiles
(thiols,
disulfides,
sulfinates,
diarylphosphine
oxides),
organyl
boronic
acids,
arylhydrazines.
Transition
metal-catalyzed,
metal-free,
electrochemical
radical
are
discussed.
also
reports
discusses
mechanistic
pathways
some
typical
reactions.
