Asian Journal of Organic Chemistry,
Год журнала:
2023,
Номер
12(11)
Опубликована: Сен. 12, 2023
Abstract
An
efficient
synthesis
of
a
variety
3‐difluoroalkyl
quinoxalin‐2(1
H
)‐ones
via
photoredox‐catalyzed
three‐component
reaction
between
)‐ones,
vinylarenes,
with
inexpensive
and
easily
accessible
difluoromethyltriphenyl
phosphonium
bromide
salt
as
the
difluoromethylated
reagent
is
described.
This
protocol
shows
excellent
reactivity,
providing
wide
range
difluoroalkyl‐substituted
in
moderate
to
yields
under
mild
conditions.
A
difluoroalkyl
radical
intermediate
was
involved
this
transformation.
European Journal of Organic Chemistry,
Год журнала:
2023,
Номер
unknown
Опубликована: Сен. 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.
Journal of the American Chemical Society,
Год журнала:
2023,
Номер
145(36), С. 20141 - 20148
Опубликована: Авг. 28, 2023
Chemodivergent
synthesis
has
been
achieved
in
asymmetric
photocatalysis.
Under
a
dual
catalyst
system
consisting
of
chiral
phosphoric
acid
and
DPZ
as
photosensitizer,
different
inorganic
bases
enabled
the
formation
two
sets
valuable
products
from
three-component
radical
tandem
transformations
2-bromo-1-arylenthan-1-ones,
styrenes,
quinoxalin-2(1H)-ones.
The
key
to
success
was
distinct
pKa
environment,
which
radicals
that
formed
on
quinoxalin-2(1H)-one
rings
after
addition
processes
underwent
either
single-electron
oxidation
or
reduction.
In
addition,
this
work
represents
first
use
quinoxalin-2(1H)-ones
photoredox
catalysis.
Angewandte Chemie International Edition,
Год журнала:
2023,
Номер
62(34)
Опубликована: Май 12, 2023
Activated
alkyl
halides
have
been
extensively
explored
to
generate
radicals
with
Ru-
and
Ir-
photocatalysts
for
1,2-difunctionalization
of
alkenes,
but
unactivated
bromides
remain
challenging
substrates
due
their
strong
reduction
potential.
Here
we
report
a
three-component
reaction
nucleophiles
(e.g.,
amines
indoles)
using
trinuclear
gold
catalyst
[Au3
(tppm)2
](OTf)3
.
It
can
achieve
the
1,2-aminoalkylation
1,2-alkylarylation
readily.
This
protocol
has
broad
scope
excellent
functional
group
compatibility
(>100
examples
up
96
%
yield).
also
affords
robust
formal
[2+2+1]
cyclization
strategy
concise
construction
pyrrolidine
skeletons
under
mild
conditions.
Mechanistic
studies
support
an
inner-sphere
single
electron
transfer
pathway
successful
cleavage
inert
C-Br
bonds.
European Journal of Organic Chemistry,
Год журнала:
2023,
Номер
26(31)
Опубликована: Июнь 15, 2023
Abstract
A
visible‐light
induced
radical
1,2‐aryl
migration
of
α,α‐diarylallyl
alcohols
was
developed
under
mild
and
metal‐free
conditions.
Commercially
available
CHCl
3
CH
2
Cl
were
used
as
tri‐
dichloromethyl
precursors.
Structurally
diverse
β‐polochloromethylated
ketones
obtained
in
good
to
moderate
yields
via
neophyl‐type
rearrangement.
Besides,
the
polychloromethyl
group
can
be
easily
transformed
into
other
useful
functional
groups.
Organic & Biomolecular Chemistry,
Год журнала:
2023,
Номер
21(35), С. 7079 - 7084
Опубликована: Янв. 1, 2023
Polychloromethylative
cyclization
of
N-alkenyl
indoles
was
developed
under
metal-free
conditions
to
afford
tricyclic
pyridoindolones
and
pyrroloindolones
in
moderate
good
yields.
In
the
reaction,
commercially
available
CHCl3
CH2Cl2
were
employed
as
tri-
dichloromethyl
radical
sources.
Moreover,
dichloromethylated
polycyclic
benzoimidazoles
can
also
be
obtained
standard
conditions.
Advanced Synthesis & Catalysis,
Год журнала:
2023,
Номер
365(19), С. 3328 - 3334
Опубликована: Авг. 4, 2023
Abstract
A
convenient
and
practical
protocol
for
the
preparation
of
SCF
3
‐containing
quinoxalin‐2(1
H
)‐one
derivatives
via
K
2
S
O
8
mediated
difunctionalization
alkenes
with
quinoxalinones
AgSCF
was
developed.
The
preliminary
study
showed
that
a
radical
triggered
cascade
reaction
process
might
be
involved
in
current
transformation.
Advanced Synthesis & Catalysis,
Год журнала:
2023,
Номер
366(2), С. 214 - 219
Опубликована: Дек. 6, 2023
Abstract
An
iron‐catalyzed
direct
C3−H
radical
trifluoromethylthiolation
of
quinoxalin‐2(1
H
)‐ones
has
been
developed.
This
protocol
uses
earth‐abundant
FeSO
4
⋅
7H
2
O
as
the
catalyst,
and
AgSCF
3
trifluoromethylthiolating
reagent
to
provide
various
SCF
‐containing
)‐one
derivatives
in
26–88%
yields.
Preliminary
mechanistic
investigations
indicate
that
reaction
proceeds
through
a
pathway.
Chinese Journal of Organic Chemistry,
Год журнала:
2024,
Номер
44(4), С. 1264 - 1264
Опубликована: Янв. 1, 2024
A
novel
three-component
cascade
radical
reaction
involving
non-activated
olefins,
quinoxalin-2(1H)-ones,
and
AgSCF3
was
proposed.Under
the
action
of
oxidizing
agent
K2S2O8,
40
quinoxaline
derivatives
containing
SCF3
were
obtained
with
highest
yield
78%.This
method
provides
a
mild
environmentally
friendly
approach
to
prepare
trifluoromethylthio-substituted
quinoxalines,
offering
advantages
such
as
high
yield,
broad
substrate
scope,
atom
economy,
environmental
efficiency.
