Photodecarboxylative C–H Alkylation of Azauracils with N-(Acyloxy)phthalimides
Satya Prakash Panda,
Sudhir Kumar Hota,
Rupashri Dash
и другие.
Organic Letters,
Год журнала:
2023,
Номер
25(20), С. 3739 - 3744
Опубликована: Май 15, 2023
We
disclose
a
transition-metal-free
NaI/PPh3-mediated
direct
C-H
alkylation
of
azauracils
using
N-(acyloxy)pthalimides
(NHPIs)
as
readily
available
alkyl
surrogates
under
visible
light
irradiation.
Detailed
mechanistic
studies
reveal
formation
photoactivated
electron
donor-acceptor
(EDA)
complex
between
NaI/PPh3,
TMEDA,
and
NHPI
ester
establish
the
crucial
role
TMEDA
in
increasing
activity
photoredox
system.
The
reaction
demonstrates
broad
scope,
scalability,
appreciable
functional
group
tolerance.
A
variety
are
shown
to
undergo
by
primary,
secondary,
tertiary
esters
mild
conditions,
furnishing
desired
products
good
excellent
yields.
Язык: Английский
Visible-light-induced radical-cascade alkylation/cyclization of acrylamides: Access to 3,3-dialkylated oxindoles
Organic & Biomolecular Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Янв. 1, 2025
A
visible-light-induced
deoxygenative
alkylation/cyclization
of
acrylamides
with
alcohols
activated
by
CS
2
has
been
developed
using
xanthate
salts
as
alkyl
radical
precursors
in
the
presence
tricyclohexylphosphine.
Язык: Английский
Silver-Catalyzed Cascade Radical Bicyclization Reaction: An Atom- and Step-Economical Strategy Accessing γ-Lactam Containing Isoquinolinediones
The Journal of Organic Chemistry,
Год журнала:
2023,
Номер
88(21), С. 15428 - 15436
Опубликована: Окт. 21, 2023
An
efficient
and
convenient
method
for
the
cascade
radical
bicyclization
of
N-phenyl-4-pentenamides
with
N-methyl-N-methacryloylbenzamides
under
silver-catalyzed
conditions
is
described.
Based
on
this
newly
developed
strategy,
a
variety
valuable
γ-lactam
containing
isoquinolinediones
can
be
effectively
synthesized
in
one
step
within
0.5
h,
during
which
two
C-C
bonds,
C-N
bond,
new
N-heterocycles
were
formed
concurrently.
With
N-aryl
allyl
carbamates,
similar
2-oxazolidinone
substituted
isoquinolinedione
compounds
likewise
produced.
The
approach
demonstrates
wide
functional
group
compatibility,
high
step-
atom-economy,
ability
to
scaled
up
gram
quantities
satisfactory
yield.
It
marks
first
instance
introducing
γ-lactams
into
isoquinoline-1,3(2H,4H)-diones
construct
linked
hybrid
drug-like
molecules,
thereby
making
strategy
highly
attractive
drug
discovery.
Язык: Английский
Visible-light-induced decarboxylative cyclization
Organic & Biomolecular Chemistry,
Год журнала:
2024,
Номер
unknown
Опубликована: Дек. 3, 2024
The
present
review
focuses
on
recent
progress
(2020–2024)
in
the
visible-light-driven
decarboxylative
cyclization
of
various
carboxylic
acid
derivatives
for
constructing
carbo-/heterocycles.
Язык: Английский
Recent advancements in iodide/phosphine-mediated photoredox radical reactions
Beilstein Journal of Organic Chemistry,
Год журнала:
2023,
Номер
19, С. 1785 - 1803
Опубликована: Ноя. 22, 2023
Photoredox
catalysis
plays
a
crucial
role
in
contemporary
synthetic
organic
chemistry.
Since
the
groundbreaking
work
of
Shang
and
Fu
on
photocatalytic
decarboxylative
alkylations
2019,
wide
range
transformations,
such
as
alkylation,
alkenylation,
cyclization,
amination,
iodination,
monofluoromethylation,
have
been
progressively
achieved
using
combination
iodide
PPh
3
.
In
this
review,
we
primarily
focus
summarizing
recent
advancements
inexpensive
readily
available
iodide/phosphine-mediated
photoredox
radical
transformations.
Язык: Английский