Organic Letters,
Год журнала:
2023,
Номер
25(50), С. 9070 - 9075
Опубликована: Дек. 13, 2023
A
Pd(II)-catalyzed
three-component
synthesis
of
2,4,6-triarylfuro[2,3-d]pyrimidines
from
β-ketodinitriles,
boronic
acids,
and
aldehydes
has
been
developed.
The
participation
both
nitrile
(-CN)
groups
led
to
the
concurrent
construction
furo-pyrimidine
via
formation
C-C,
C═C,
C-O,
C-N,
C═N
bonds.
compounds
show
excellent
photoluminescence
properties
with
absorption
maxima
ranging
348
387
nm
emission
468
533
nm.
synthetic
utility
protocol
was
further
demonstrated
through
a
few
postsynthetic
manipulations.
Green Chemistry,
Год журнала:
2023,
Номер
25(20), С. 7971 - 7977
Опубликована: Янв. 1, 2023
Alkyl
diacyl
peroxides
were
demonstrated
to
be
efficient
alkylating
reagents
for
the
visible-light-induced
4CzIPN-catalyzed
direct
C–H
alkylation
of
N
-heteroaromatics.
The Journal of Organic Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Фев. 13, 2025
Herein,
we
report
sodium
iodide
(NaI)-catalyzed
decarboxylative
C–H
alkylation
of
azauracils
with
N-hydroxyphthalimide
(NHPI)
esters
facilitated
by
visible
light
activation
catalytic
electron
donor–acceptor
(EDA)
complexes.
Control
experiments
and
density
functional
theory
calculations
suggest
that
the
coupling
reaction
proceeds
via
a
transiently
assembled
EDA
complex
between
NHPI
ester
NaI
in
N,N-dimethylacetamide
solvent.
This
synthetic
method
efficiently
applies
to
primary,
secondary,
tertiary
under
mild,
photocatalyst-free,
redox-neutral
conditions,
achieving
high
yields
desired
alkylated
azauracils.
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.
Organic Letters,
Год журнала:
2023,
Номер
25(48), С. 8541 - 8546
Опубликована: Окт. 11, 2023
We
report
herein
a
protocol
for
the
selective
activation
of
C(sp3)–H
bonds
based
on
interplay
two
readily
available
organic
catalysts
and
their
successful
implementation
in
cross-coupling
azaarenes
with
alkanes.
This
Minisci-like
reaction
is
promoted
by
visible
light
at
room
temperature
free
from
chemical
oxidants,
metals,
chlorinated
solvents.
A
wide
range
substrates
are
compatible,
including
some
bioactive
molecules.
Mechanistic
studies
support
dual
catalytic
cycle
H2
evolution.
Chemical Reviews,
Год журнала:
2024,
Номер
124(17), С. 10192 - 10280
Опубликована: Авг. 8, 2024
Radical
C–H
functionalization
represents
a
useful
means
of
streamlining
synthetic
routes
by
avoiding
substrate
preactivation
and
allowing
access
to
target
molecules
in
fewer
steps.
The
first-row
transition
metals
(Ti,
V,
Cr,
Mn,
Fe,
Co,
Ni,
Cu)
are
Earth-abundant
can
be
employed
regulate
radical
functionalization.
use
such
is
desirable
because
the
diverse
interaction
modes
between
metal
complexes
species
including
addition
center,
ligand
complexes,
substitution
single-electron
transfer
radicals
hydrogen
atom
noncovalent
complexes.
Such
interactions
could
improve
reactivity,
diversity,
selectivity
transformations
allow
for
more
challenging
reactions.
This
review
examines
achievements
this
promising
area
over
past
decade,
with
focus
on
state-of-the-art
while
also
discussing
existing
limitations
enormous
potential
high-value
regulated
these
metals.
aim
provide
reader
detailed
account
strategies
mechanisms
associated
Organic Letters,
Год журнала:
2024,
Номер
26(18), С. 3727 - 3732
Опубликована: Апрель 28, 2024
Photoexcitation
electron
donor-acceptor
(EDA)
complexes
provide
an
effective
approach
to
produce
radicals
under
mild
conditions,
while
the
catalytic
version
of
EDA
complex
photoactivation
remains
scarce.
Herein,
we
report
a
visible-light-induced
organophotocatalytic
pathway
for
cyanoalkylation
azauracils
using
inexpensive
and
readily
available
1,4-diazabicyclo[2.2.2]octane
(DABCO)
as
donor.
This
synthetic
method
exhibits
exceptional
compatibility
with
various
functional
groups
presents
34
examples
in
high
yields.
The
efficient
offers
environmentally
friendly
sustainable
route
toward
enhancing
structural
diversity
azauracils.
Organic Letters,
Год журнала:
2024,
Номер
26(34), С. 7227 - 7232
Опубликована: Авг. 20, 2024
We
present
an
electrochemical
alkylation
of
azauracils
using
N-(acyloxy)phthalimides
(NHPI
esters)
as
readily
available
alkyl
radical
progenitors
under
metal-
and
additive-free
conditions.
Several
are
shown
to
undergo
with
array
NHPI
esters
(1°,
2°,
3°,
sterically
congested),
providing
the
desired
products
in
good
excellent
yields.
This
operationally
simple
method
is
robust,
scalable,
suitable
for
both
batch
flow
setups.
Chemical Communications,
Год журнала:
2024,
Номер
60(27), С. 3665 - 3668
Опубликована: Янв. 1, 2024
An
innovative
and
eco-friendly
method
has
been
developed
for
synthesizing
6-arylated
or
6-alkylated
1,2,4-triazine-3,5(2
H
,4
)-diones,
utilizing
a
photoinduced
cross-dehydrogenative
coupling
reaction
with
hydrazines.
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(10), С. 7233 - 7242
Опубликована: Апрель 26, 2024
A
self-catalyzed,
visible-light-induced,
directly
selective
C3–H
aroylation
of
quinoxalin-2(1H)-ones
via
energy
transfer
and
hydrogen
atom
(HAT)
catalysis
has
been
developed.
The
method
is
highly
atom-economical,
eco-friendly,
easy
to
handle.
Notably,
the
reaction
proceeded
efficiently
with
ambient
air
as
sole
oxidant
at
room
temperature.
European Journal of Organic Chemistry,
Год журнала:
2024,
Номер
27(7)
Опубликована: Янв. 19, 2024
Abstract
A
Minisci‐type
carbamoylation
of
azauracils
was
developed
to
afford
6‐carbamoyl
in
yields
up
94
%.
In
this
transformation,
oxamic
acids
were
employed
as
the
carbamoyl
radical
sources
under
metal‐free
conditions.
It
features
high
atom
economy,
good
functional
group
compatibility
and
convenient
operation.
