European Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
27(47)
Published: Aug. 26, 2024
Abstract
Regioselectively
arylated
heteroarenes
are
privileged
scaffolds
with
remarkable
biological
and
optoelectronic
properties.
Traditional
arylation
approaches
based
on
the
transition‐metal
catalysis
present
various
issues
related
to
cost
of
synthesis
environmental
sustainability.
The
growing
applications
arylheteroarenes
in
pharmaceuticals
cutting‐edge
technologies
have
fuelled
interest
development
green
cost‐effective
synthetic
approaches.
This
article
reports
recent
progress
transition‐metal‐free
strategies
for
regioselective
C−H
arylation/heteroarylation
heteroarenes.
arylations
several
five‐
six‐membered,
nitrogen,
oxygen
sulphur
containing
using
reagents
comprehensively
reviewed.
Chemical Reviews,
Journal Year:
2023,
Volume and Issue:
123(8), P. 4237 - 4352
Published: Jan. 24, 2023
The
emergence
of
modern
photocatalysis,
characterized
by
mildness
and
selectivity,
has
significantly
spurred
innovative
late-stage
C–H
functionalization
approaches
that
make
use
low
energy
photons
as
a
controllable
source.
Compared
to
traditional
strategies,
photocatalysis
paves
the
way
toward
complementary
and/or
previously
unattainable
regio-
chemoselectivities.
Merging
compelling
benefits
with
workflow
offers
potentially
unmatched
arsenal
tackle
drug
development
campaigns
beyond.
This
Review
highlights
photocatalytic
strategies
small-molecule
drugs,
agrochemicals,
natural
products,
classified
according
targeted
bond
newly
formed
one.
Emphasis
is
devoted
identifying,
describing,
comparing
main
mechanistic
scenarios.
draws
critical
comparison
between
established
ionic
chemistry
photocatalyzed
radical-based
manifolds.
aims
establish
current
state-of-the-art
illustrate
key
unsolved
challenges
be
addressed
in
future.
authors
aim
introduce
general
readership
functionalization,
specialist
practitioners
evaluation
methodologies,
potential
for
improvement,
future
uncharted
directions.
Green Chemistry,
Journal Year:
2023,
Volume and Issue:
25(8), P. 3292 - 3296
Published: Jan. 1, 2023
The
semi-heterogeneous
g-C
3
N
4
/NaI
dual
catalytic
system
driven
C–C
bond
formation
between
quinoxalin-2(1
H
)-ones
and
arylhydrazines
under
blue
light
irradiation
is
reported
for
the
first
time.
Green Chemistry,
Journal Year:
2023,
Volume and Issue:
25(20), P. 7971 - 7977
Published: Jan. 1, 2023
Alkyl
diacyl
peroxides
were
demonstrated
to
be
efficient
alkylating
reagents
for
the
visible-light-induced
4CzIPN-catalyzed
direct
C–H
alkylation
of
N
-heteroaromatics.
Chemical Reviews,
Journal Year:
2024,
Volume and Issue:
unknown
Published: Sept. 13, 2024
Hypervalent
iodine(III)
compounds
have
found
wide
application
in
modern
organic
chemistry
as
environmentally
friendly
reagents
and
catalysts.
iodine
are
commonly
used
synthetically
important
halogenations,
oxidations,
aminations,
heterocyclizations,
various
oxidative
functionalizations
of
substrates.
Iodonium
salts
arylating
reagents,
while
iodonium
ylides
imides
excellent
carbene
nitrene
precursors.
Various
derivatives
benziodoxoles,
such
azidobenziodoxoles,
trifluoromethylbenziodoxoles,
alkynylbenziodoxoles,
alkenylbenziodoxoles
group
transfer
the
presence
transition
metal
catalysts,
under
metal-free
conditions,
or
using
photocatalysts
photoirradiation
conditions.
Development
hypervalent
catalytic
systems
discovery
highly
enantioselective
reactions
chiral
represent
a
particularly
recent
achievement
field
chemistry.
Chemical
transformations
promoted
by
many
cases
unique
cannot
be
performed
any
other
common,
non-iodine-based
reagent.
This
review
covers
literature
published
mainly
last
7-8
years,
between
2016
2024.
The Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
89(9), P. 6117 - 6125
Published: April 24, 2024
The
first
paired
electrolysis-enabled
arylation
of
quinoxalin-2(1H)-ones
was
achieved
using
cyanoarenes
as
the
reagents.
A
variety
3-arylquinoxalin-2(1H)-ones
with
various
important
functional
groups
were
obtained
in
moderate
to
good
yields
under
metal-
and
chemical
oxidant-free
conditions.
With
a
pair
reductive
oxidative
processes
occurring
among
substrates
reaction
intermediates,
power
consumption
can
be
dramatically
reduced.
The Journal of Organic Chemistry,
Journal Year:
2022,
Volume and Issue:
87(16), P. 10947 - 10957
Published: Aug. 4, 2022
A
photoredox-catalyzed
direct
arylation
of
quinoxalin-2-(1H)-ones
using
diaryliodonium
triflates
as
the
convenient,
stable,
and
cheap
aryl
source
is
described.
broad
variety
are
shown
to
react
with
structurally
electronically
diverse
triflates,
allowing
efficient
access
a
wide
pharmaceutically
important
3-arylquinoxalin-2-(1H)-ones.
The
presented
method
attractive
regard
operational
simplicity,
mild
conditions,
scope,
scalability,
high
functional
group
tolerance.
European Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
unknown
Published: Sept. 11, 2023
Abstract
The
multicomponent
reactions
of
quinoxalin‐2(1
H
)‐ones
has
attracted
considerable
interest
due
to
their
significant
biological
and
chemical
activities.
very
recent
advances
(from
2021
the
beginning
2023)
on
radical
three‐component
cascade
reaction
)‐one
derivatives
at
C3
position
were
summarized
in
this
mini‐review.
According
kind
types
involved,
some
representative
examples
detailed
mechanism
have
been
categorized
discussed.
red
front
was
covered
by
Figure
1.
Organic Letters,
Journal Year:
2023,
Volume and Issue:
25(24), P. 4422 - 4428
Published: June 8, 2023
Presented
herein
is
a
condition-controlled
selective
synthesis
of
pyranone-tethered
indazoles
or
carbazole
derivatives
via
the
cascade
reactions
N-nitrosoanilines
with
iodonium
ylides.
Mechanistically,
formation
former
involves
an
unprecedented
process
including
nitroso
group-directed
C(sp2)–H
bond
alkylation
N-nitrosoaniline
ylide
followed
by
intramolecular
C-nucleophilic
addition
to
moiety,
solvent-assisted
cyclohexanedione
ring
opening,
and
transesterification/annulation.
On
contrary,
latter
initial
annulation
denitrosation.
These
developed
protocols
feature
easily
controllable
selectivity,
mild
reaction
conditions,
clean
sustainable
oxidant
(air),
valuable
products
that
are
structurally
diverse.
In
addition,
utility
was
showcased
their
facile
diverse
transformations
into
synthetically
biologically
interesting
compounds.
