Organic Letters,
Год журнала:
2024,
Номер
26(29), С. 6098 - 6102
Опубликована: Июль 15, 2024
We
disclose
the
synthesis
of
3-arylquinoxalin-2-ones
from
o-phenylenediamines
and
readily
available
arylacetates.
The
method
harnesses
selective
oxidative
property
elemental
sulfur
in
presence
amine
base
catalyst
DMSO.
reactions
are
operationally
simple
tolerate
a
wide
range
functional
groups.
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(9), С. 6117 - 6125
Опубликована: Апрель 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.
Organic Letters,
Год журнала:
2024,
Номер
26(15), С. 3189 - 3194
Опубликована: Апрель 8, 2024
A
new
umpolung
approach
to
the
C3–H
functionalization
of
indoles
with
diverse
nucleophiles
based
on
intermediate
formation
I(III)
reagents
is
described.
The
3,5-dimethylisoxazol-4-yl
auxiliary
allows
for
selective
indole
transfer
under
catalyst-free
conditions,
which
was
impossible
using
previously
reported
reagents.
Combining
mildness
transition-metal-free
conditions
and
high
reactivity
hypervalent
iodine
reagents,
this
protocol
tolerates
various
functional
groups
provides
access
that
are
difficult
prepare
conventionally.
Abstract
Visible‐light‐activated
organic
reactions
unlock
novel
avenues
for
complex
molecular
transformations,
impossible
under
standard
“thermal”
conditions,
which
makes
them
powerful
tools
in
the
arsenal
of
synthetic
chemistry.
However,
transition
metal‐based
or
photoredox
catalysts
are
often
used
to
ensure
productive
absorption
visible
light,
might
be
not
desirable
medicinal
chemistry
and
industry
due
toxicity,
low
sustainability,
high
cost
most
photocatalysts.
A
more
environmentally
economically
benign
approach
is
based
on
formation
transient
electron
donor‐acceptor
(EDA)
complexes
between
two
reagents
a
reagent
an
additive,
that
readily
absorb
acting
as
internal
photosensitizers.
Within
EDA
complex‐based
arylation
strategies,
chemical
transformations
mediated
by
noncovalent
interaction
molecules,
namely
electron‐poor
aryl
halides
their
equivalents
electron‐rich
nucleophilic
additives.
Moreover,
besides
stoichiometric
organocatalysis
can
achieved
certain
cases
through
regeneration
donor
molecules
course
reaction.
Photoexcitation
induces
single
transfer
(SET)
process
generate
radical
species
step.
This
Review
will
focus
state‐of‐the‐art
strategies
utilizing
halides,
aryldiazonium,
diaryliodonium,
arylsulfonium
arylphosphonium
salts
reactants,
published
mainly
last
five
years.
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(14), С. 10112 - 10126
Опубликована: Июль 3, 2024
A
photoredox-promoted
decarboxylative
C-H
glycosylation
for
the
synthesis
of
nonclassical
heteroaryl
C-glycosides
is
reported.
This
methodology
characterized
by
an
exceedingly
simple
reaction
system,
high
diastereoselectivity,
and
good
functional
group
tolerance.
Moreover,
operational
procedure
simple,
gram-scale
highlights
practical
applicability
this
protocol.
Advanced Synthesis & Catalysis,
Год журнала:
2024,
Номер
unknown
Опубликована: Июнь 13, 2024
Abstract
A
visible‐light‐promoted
strategy
for
the
decarboxylative
C‐3
carbamoylation
of
quinoxalinone
scaffolds
is
developed.
This
approach
initiates
through
formation
an
EDA
complex
between
oxamic
acid
and
quinoxalinone.
Successive
SET
construct
C−C
bond.
method
utilizes
aerial
oxygen
as
green
oxidant
eradicates
process
from
use
external
photocatalysts
transition
metals.
Detailed
synthetic
photophysical
studies
enlighten
reaction
pathway.
Organic Letters,
Год журнала:
2024,
Номер
26(37), С. 7864 - 7868
Опубликована: Сен. 9, 2024
A
hypervalent
iodine-reagent-based
C-H
functionalization
strategy
was
utilized
to
synthesize
diaryl
ethers.
This
method
directly
transforms
various
arenes
into
their
corresponding
diaryliodonium
salts,
followed
by
a
C-O
coupling
reaction
produce
structurally
diverse
The
efficacy
of
this
approach
in
the
late-stage
structural
modifications
complex
molecules
demonstrated.
Chinese Journal of Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Янв. 16, 2025
Comprehensive
Summary
Herein,
we
report
a
photo‐induced,
metal‐/additive‐free
protocol
for
the
difluoromethylation
of
N
‐heteroaromatics
with
[bis(difluoroacetoxy)iodo]benzene
as
reagent.
The
affords
difluoromethylated
in
moderate
to
good
yield
(up
91%).
transformation
is
compatible
wide
range
substrates
and
has
tolerance
towards
various
functional
groups.
Moreover,
synthetic
value
this
method
further
demonstrated
by
applications
gram‐scale
synthesis
late‐stage
functionalization
biologically
important
molecules.
Organic Letters,
Год журнала:
2025,
Номер
27(4), С. 1012 - 1017
Опубликована: Янв. 21, 2025
Vicinal
bis(tetraarylphosphonium)
salts
have
scarcely
been
reported
in
the
literature.
In
this
study,
we
demonstrate
that
visible-light-induced
difunctionalization
of
ortho-trifluoromethylsulfonylated
diaryliodonium
conveniently
furnishes
bis(phosphonium)
without
additional
catalysts
or
photoinitiators.
The
methodology
establishes
a
practical
platform
for
preparation
using
readily
available
tertiary
phosphines.
are
anticipated
to
garner
great
deal
interest
catalytic
and
medicinal
chemistry.
Chemical Reviews,
Год журнала:
2025,
Номер
unknown
Опубликована: Март 7, 2025
Constructing
chemical
bonds
under
green
sustainable
conditions
has
drawn
attention
from
environmental
and
economic
perspectives.
The
dissociation
of
(hetero)aryl-halide
is
a
crucial
step
most
arylations
affording
(hetero)arene
derivatives.
Herein,
we
summarize
the
(hetero)aryl
halides
activation
enabling
direct
(hetero)arylation
trapping
reagents
construction
highly
functionalized
(hetero)arenes
benign
conditions.
strategies
for
aryl
iodides
are
classified
into
(a)
hypervalent
iodoarene
followed
by
functionalization
thermal/photochemical
conditions,
(b)
aryl-I
bond
in
presence
bases
with/without
organic
catalysts
promoters,
(c)
photoinduced
presence/absence
organophotocatalysts,
(d)
electrochemical
direct/indirect
electrolysis
mediated
organocatalysts
mediators
acting
as
electron
shuttles,
(e)
electrophotochemical
redox-active
organocatalysts.
These
modes
result
exhibiting
diverse
reactivity
formal
cations/radicals/anions
aryne
precursors.
coupling
these
reactive
intermediates
with
leads
to
facile
selective
formation
C-C
C-heteroatom
bonds.
ecofriendly,
inexpensive,
functional
group-tolerant
offer
alternatives
transition
metal-based
catalysis.