European Journal of Organic Chemistry,
Год журнала:
2022,
Номер
2022(35)
Опубликована: Авг. 12, 2022
Abstract
A
new
photoinduced
acylation/arylation
of
N
‐(arylsulfonyl)acrylamide
with
acyl
oxime
esters
through
a
nitrogen‐centered
radical
protocol
has
been
disclosed
for
efficient
preparation
functionalized
indolin‐2‐ones,
which
proceeds
cascade
addition
carbon‐carbon
double
bond,
aryl
migration,
desulfonylation,
and
intramolecular
cyclization
sequence.
This
redox‐neutral
strategy
features
excellent
selectivity,
good
substituent
tolerance,
wide
substrate
scope.
Organic Letters,
Год журнала:
2023,
Номер
25(38), С. 7014 - 7019
Опубликована: Сен. 18, 2023
Organoelectrophotocatalytic
generation
of
acyl
radicals
from
formamides
and
aldehydes
to
synthesize
acylated
3-CF3-2-oxindoles
has
been
developed.
This
protocol
features
a
monocatalytic
system
using
9,10-phenanthrenequinone
(PQ)
both
as
catalyst
hydrogen
atom
transfer
(HAT)
reagent,
which
avoids
the
use
an
external
HAT
metal
oxidant.
A
variety
have
obtained
in
satisfactory
yields
CF3-substituted
N-arylacrylamides
via
tandem
radical
cyclization.
Organic Letters,
Год журнала:
2023,
Номер
25(7), С. 1161 - 1165
Опубликована: Фев. 9, 2023
The
visible-light-induced
photoredox
carbon
radical
formation
from
aqueous
sulfoxonium
ylides
has
been
demonstrated
for
the
first
time.
While
direct
reduction
of
by
H2O
efficiently
generates
corresponding
hydrocarbon
compounds,
use
additional
alkenes
as
acceptors
alters
chemical
reactivity
to
achieve
alkene
carboarylation
N-arylacrylamides.
Mechanistic
studies
reveal
two
different
reaction
pathways
involved
in
resulting
release
dimethyl
sulfone
and
form
DMSO.
Advanced Synthesis & Catalysis,
Год журнала:
2024,
Номер
366(4), С. 635 - 697
Опубликована: Янв. 13, 2024
Abstract
In
recent
years,
the
interest
to
develop
cyclizations
promoted
by
visible
light
has
been
gaining
a
lot
of
attention
due
its
sustainability
aspect.
this
review,
we
summarize
most
important
advances
in
period
describing
methods
used
generate
different
ring
sizes,
while
focusing
on
mechanistic
details
these
reactions.
RSC Sustainability,
Год журнала:
2024,
Номер
2(8), С. 2169 - 2189
Опубликована: Янв. 1, 2024
This
review
describes
the
recent
advancements
in
visible
light-induced
bromine
radical
enhanced
hydrogen
atom
transfer
(HAT)
reactions
organic
synthesis.
Chinese Journal of Chemistry,
Год журнала:
2024,
Номер
42(11), С. 1230 - 1236
Опубликована: Фев. 5, 2024
Comprehensive
Summary
A
visible‐light‐enabled,
photocatalyst‐free
hydroacylation
reaction
of
azodicarboxylic
acid
derivatives
was
described.
This
radical
conjugate
addition
(RCA)
protocol
relied
on
the
dual
role
4‐acyl‐1,4‐dihydropyridine
(acyl‐DHP)
reagents
that
besides
being
as
reservoirs,
they
also
enabled
conversion
adducts
to
anion
intermediates
via
reduction.
Under
“catalyst‐oxidant‐additive
free”
conditions,
a
wide
range
structurally
different
acyl
hydrazide
products
were
readily
obtained
in
56%—99%
yields.
The
utility
this
transformation
further
demonstrated
by
scale‐up
synthesis
and
downstream
derivatization.
The Journal of Organic Chemistry,
Год журнала:
2023,
Номер
88(16), С. 12121 - 12130
Опубликована: Июль 29, 2023
We
describe
a
visible-light
photoredox-catalyzed
alkylation/arylative
cyclization
of
N-acrylamides─from
2-arylindoles,
2-arylbenzimidazoles,
or
N-substituted
anilines─with
ketone-derived
dihydroquinazolinones,
accessing
indolo-
and
benzimidazolo[2,1-a]isoquinolines
2-oxindoles.
The
consecutive
incorporation
alkyl-
aryl-carbogenic
motifs
across
C=C
bond
via
formal
cleavage
ketone
α-C-C
arene
C-H
bonds
leads
to
the
formation
five-
six-membered
rings,
with
an
all-carbon
quaternary
stereocenter.
This
dicarbofunctionalization
elaborates
aromatization-driven
radical
C-C
functionalization
unactivated
aliphatic
ketones
construct
diverse
cyclic
structures
functionality
tolerance.
The Journal of Organic Chemistry,
Год журнала:
2023,
Номер
88(9), С. 5431 - 5439
Опубликована: Апрель 24, 2023
Visible
light-mediated
facile
synthesis
of
heteroarenes,
namely,
isoquinolines,
benzothiazoles,
and
quinazolines,
is
demonstrated
by
employing
isocyanides
inexpensive
acyl
peroxides.
It
shown
for
the
first
time
that
singlet-excited
decompose
peroxides
into
aryl/alkyl
radicals.
The
latter
attack
isocyanides,
yielding
imidoyl
radicals
subsequently
cyclize
to
afford
heteroarene
products.
protocol
involving
radical
cascade
reactions
obviates
requirement
any
external
photocatalyst,
oxidant,
additive,
base.
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(11), С. 7531 - 7540
Опубликована: Май 18, 2024
An
organocatalyzed
photoelectrochemical
method
for
the
generation
of
acyl
and
phosphoryl
radicals
from
formamides,
aldehydes,
phosphine
oxides
has
been
developed.
This
protocol
utilizes
9,10-phenanthrenequinone
(PQ)
as
both
a
molecular
catalyst
hydrogen
atom-transfer
(HAT)
reagent,
eliminating
requirement
external
metal-based
reagents,
HAT
oxidants.
The
generated
can
be
applied
to
range
radical-mediated
transformation
reactions,
including
C–H
carbamoylation
heteroarenes,
intermolecular
tandem
radical
cyclization
CF3-substituted
N-arylacrylamides,
well
intramolecular
reactions.
use
in
these
transformations
offers
an
efficient
sustainable
approach
accessing
structurally
diverse
carbonyl
compounds.
The Journal of Organic Chemistry,
Год журнала:
2023,
Номер
88(21), С. 15389 - 15394
Опубликована: Окт. 24, 2023
Herein,
we
report
the
first
metal-free,
redox-neutral
strategy
for
radical
cascade
alkylative
addition,
cyclization
of
N-arylacrylamides
with
unactivated
alkyl
chlorides
to
give
corresponding
3,3-disubstituted
oxindoles
in
moderate
good
yields.
This
transformation's
salient
features
are
utilization
an
organo
photocatalyst,
mild
reaction
conditions,
and
broad
substrate
scope.
Moreover,
this
methodology
is
suitable
hetero
cycle
derived
acrylamides
further
allowed
utilize
aryl
reaction.
Finally,
DFT
studies
allow
us
shed
light
on
mechanism.
The Journal of Organic Chemistry,
Год журнала:
2023,
Номер
88(7), С. 4422 - 4433
Опубликована: Март 17, 2023
The
development
of
excited-state
palladium-catalyzed
alkylative
cyclization
acrylamides
and
the
alkylation
quinoxalinones
is
described.
application
a
variety
primary,
secondary,
tertiary
unactivated
alkyl
halides
as
radical
precursors
use
simple
catalyst
system
are
highlights
this
reactivity
manifold.
reactions
exhibit
wide
scope,
occur
under
mild
conditions,
furnish
products
in
excellent
yields.
