Abstract
A
new
protocol
for
accessing
3,4-dihydroquinolin-2(1H)-ones
was
established
through
a
sequence
of
iron-catalyzed
photoredox
generation
carbamoyl
radicals
from
oxamic
acids,
addition
the
to
electron-deficient
alkenes,
intramolecular
cyclization,
and
aromatization.
The
process
is
compatible
with
variety
N-phenyloxamic
acids
monosubstituted,
1,1-disubstituted,
trisubstituted
alkenes.
Employing
cheap,
readily
available,
environmentally
benign
iron
as
catalyst,
provides
an
excellent
alternative
synthesis
3,4-dihydroquinolin-2(1H)-ones.
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:
2022,
Номер
24(45), С. 8265 - 8270
Опубликована: Ноя. 7, 2022
The
greener
synthesis
of
N-substituted
isonicotinamides
is
high
importance
and
remains
a
significant
challenge
to
the
chemistry
community.
Herein
we
delineated
visible-light-driven,
transition-metal-free,
external-oxidant-free
radical-radical
cross-coupling
reaction
access
via
consecutive
photoinduced
electron
transfer
(ConPET).
utility
this
protocol
highlighted
through
N-terminal
modification
peptides
late-stage
drugs.
Chemical Science,
Год журнала:
2023,
Номер
14(36), С. 9806 - 9813
Опубликована: Янв. 1, 2023
A
direct
intermolecular
decarboxylative
Giese
amidation
reaction
from
bench
stable,
non-toxic
and
environmentally
benign
oxamic
acids
has
been
developed,
which
allows
for
easy
access
to
1,4-difunctionalised
compounds
are
not
otherwise
readily
accessible.
Crucially,
a
more
general
acceptor
substrate
scope
is
now
possible,
renders
the
applicable
complex
substrates
such
as
natural
products
chiral
building
blocks.
Two
different
photocatalytic
methods
(one
via
oxidative
other
reductive
quenching
cycles)
one
metal-
light-free
method
were
developed
flexibility
provided
by
conditions
proved
be
crucial
enabling
scope.
Organic Letters,
Год журнала:
2024,
Номер
26(4), С. 860 - 865
Опубликована: Янв. 22, 2024
β-Amidated
carboxylic
acids,
or
succinamic
acid
derivatives,
constitute
a
valuable
chemical
scaffold
with
broad
applications
in
pharmaceuticals,
agrochemicals,
and
polymer
sciences.
Herein,
we
report
redox-neutral
multicomponent
reaction
for
the
synthesis
of
derivatives
good
yields.
This
protocol
involves
styrene,
CO2
1,4-carbamoyl-dihydropyridine
as
radical
precursors.
The
method
exhibits
substrate
scope
under
mild
conditions,
including
late-stage
functionalization.
Moreover,
by
employing
13CO2,
enables
labeled
1,2-dicarboxylic
compounds.
Organic & Biomolecular Chemistry,
Год журнала:
2024,
Номер
22(9), С. 1821 - 1833
Опубликована: Янв. 1, 2024
Metal-free
synthesis
of
medicinally
important
carbamoylated
dihydroquinolinones
using
readily
available,
cheap
and
environment-friendly
materials
with
good
to
excellent
yields.
ACS Catalysis,
Год журнала:
2024,
Номер
14(8), С. 5972 - 5977
Опубликована: Апрель 4, 2024
We
report
carbamoylarylation
of
alkenes
using
N-aryl
oxamic
acid
derivatives
under
visible-light
irradiation.
Reactions
with
carbamoyl
radicals
generated
to
afford
Giese-type
products
or
3,4-dihydroquinolin-2(1H)-ones
via
ortho-radical
addition
an
aryl
amide
moiety
have
been
previously
reported.
However,
this
study
reveals
that
the
introduction
a
removable
bulky
group
onto
nitrogen
atom
acids
facilitates
radical
alkenes,
resulting
in
1,4-aryl
migration
C(aryl)–N
bond
cleavage,
thus
affording
arylpropanamides.
Various
such
as
acrylic
and
styrene
derivatives,
are
successfully
applied
synthesis
variety
arylpropanamide
including
1,4-dicarbonyl
amides,
forming
two
C–C
bonds.
Organic Letters,
Год журнала:
2023,
Номер
26(14), С. 2768 - 2772
Опубликована: Окт. 5, 2023
An
efficient
methodology
for
the
photoredox-
and
nickel-catalyzed
aminocarbonylation
of
(hetero)aryl
bromides
was
developed.
The
utilization
readily
available
oxamic
acids,
application
a
broadly
used
organic
photoredox
catalyst
(4CzIPN),
mild
reaction
conditions
make
this
transformation
an
appealing
alternative
to
classical
amidation
procedures.
generation
carbamoyl
radicals
supported
by
trapping
reactions
with
hydrogen
atom
transfer
in
presence
D2O,
yielding
deuterated
formamide.
generality
deuteration
protocol
confirmed
various
acids.
Chemical Communications,
Год журнала:
2024,
Номер
60(62), С. 8107 - 8110
Опубликована: Янв. 1, 2024
A
visible-light-induced
directed
decarboxylative
disulfuration
of
α-keto
acids
and
oxamic
was
developed.
As
a
result,
series
versatile
mono
acyl
disulfide
derivatives
synthesized
under
mild
sustainable
reaction
conditions.
This
protocol
has
broad
substrate
scope,
good
functional-group
tolerance,
excellent
synthetic
applications.
