Chemistry - A European Journal,
Год журнала:
2023,
Номер
29(50)
Опубликована: Июнь 2, 2023
Alkyl
radical
precursors
are
essential
for
a
wide
variety
of
photocatalytic
and
3d-metal-catalyzed
C-C
bond
forming
reactions.
Neutral
organic
heterocycles
as
electroauxiliaries
such
4-alkyl
Hantzsch
esters
have
become
reliable
tools
alkyl
formation.
Here
we
show
that
2,2'-biquinoline-derived
alkyl-substituted
dihydroquinolines
act
competent
with
the
ability
to
form
primary,
secondary
tertiary
radicals.
Hydroalkylation
benzalmalononitriles
N-Boc
protected
diazenes
has
been
achieved
through
copper
catalysis
under
mild
conditions
50
°C
good
very
yields
up
85
%.
Furthermore,
dihydroquinolines'
reactivity
towards
denitrative
alkylation
nitroolefins
β-nitrostyrene
was
discovered.
Most
importantly,
released
biquinoline
can
be
recycled,
which
greatly
improves
overall
atom-economy
these
in
comparison
previous
N-heterocyclic
electroauxiliaries.
Angewandte Chemie International Edition,
Год журнала:
2023,
Номер
62(34)
Опубликована: Июнь 28, 2023
Activation
of
C-C
bonds
allows
editing
molecular
skeletons,
but
methods
for
selective
activation
nonpolar
in
the
absence
a
chelation
effect
or
driving
force
derived
from
opening
strained
ring
are
scarce.
Herein,
we
report
method
ruthenium-catalyzed
pro-aromatic
compounds
by
means
π-coordination-enabled
aromatization.
This
was
effective
cleavage
C-C(alkyl)
and
C-C(aryl)
ring-opening
spirocyclic
compounds,
providing
an
array
benzene-ring-containing
products.
The
isolation
methyl
ruthenium
complex
intermediate
supports
mechanism
involving
ruthenium-mediated
bond
cleavage.
Angewandte Chemie,
Год журнала:
2024,
Номер
136(8)
Опубликована: Янв. 5, 2024
Abstract
A
mild
photoredox
catalyzed
construction
of
sulfides,
disulfides,
selenides,
sulfoxides
and
sulfones
from
unstrained
ketone
precursors
is
introduced.
Combination
this
deacylative
process
with
S
N
2
or
coupling
reactions
provides
novel
convenient
modular
strategies
toward
unsymmetrical
symmetric
disulfides.
Reactivity
studies
favor
a
bromine
radical
that
initiates
HAT
(Hydrogen
Atom
Transfer)
the
aminal
intermediate
resulting
in
expulsion
C‐centered
intercepted
to
make
C−S
C−Se
bonds.
Gram
scale
reactions,
broad
substrate
scope
tolerance
towards
various
functional
groups
render
method
appealing
for
future
applications
synthesis
organosulfur
selenium
complexes.
Organic Letters,
Год журнала:
2024,
Номер
26(44), С. 9503 - 9507
Опубликована: Окт. 28, 2024
Herein,
we
describe
a
dual
catalytic
strategy
that
employs
dihydroquinazolinones,
derived
from
ketone
analogs,
as
versatile
intermediates
for
acylation
via
α
C–C
cleavage
with
2-pyridyl
esters,
facilitating
the
efficient
synthesis
of
variety
ketones.
The
reaction
accommodates
wide
range
ketones
and
carboxylic
acids,
showing
tolerance
to
various
functional
groups.
versatility
this
synthetic
technique
is
further
highlighted
through
its
application
in
late-stage
modification
pharmaceuticals
biologically
active
natural
products.
Chemistry - A European Journal,
Год журнала:
2023,
Номер
29(50)
Опубликована: Июнь 2, 2023
Alkyl
radical
precursors
are
essential
for
a
wide
variety
of
photocatalytic
and
3d-metal-catalyzed
C-C
bond
forming
reactions.
Neutral
organic
heterocycles
as
electroauxiliaries
such
4-alkyl
Hantzsch
esters
have
become
reliable
tools
alkyl
formation.
Here
we
show
that
2,2'-biquinoline-derived
alkyl-substituted
dihydroquinolines
act
competent
with
the
ability
to
form
primary,
secondary
tertiary
radicals.
Hydroalkylation
benzalmalononitriles
N-Boc
protected
diazenes
has
been
achieved
through
copper
catalysis
under
mild
conditions
50
°C
good
very
yields
up
85
%.
Furthermore,
dihydroquinolines'
reactivity
towards
denitrative
alkylation
nitroolefins
β-nitrostyrene
was
discovered.
Most
importantly,
released
biquinoline
can
be
recycled,
which
greatly
improves
overall
atom-economy
these
in
comparison
previous
N-heterocyclic
electroauxiliaries.
