Synthesis,
Год журнала:
2023,
Номер
55(24), С. 4113 - 4144
Опубликована: Авг. 2, 2023
Abstract
We
report
the
Pd(II)-catalyzed,
picolinamide-directed
δ-C(sp2)–H
(ortho)
functionalization
of
phenylalaninol
scaffolds.
Assembling
δ-C–H
arylated,
alkylated,
benzylated,
alkenylated,
brominated,
and
iodinated
scaffolds
was
accomplished.
The
arylation
reaction
occurred
under
neat
conditions.
Hydrolysis
picolinamide
moiety
synthetic
utility
arylated
substrates
were
explored.
have
also
shown
preparation
some
modified
Matijin–Su
(aurantiamide)
derivatives
using
bis
compounds
obtained
from
(Matijin–Su
is
an
anti-HBV
agent
possessing
unit).
Considering
importance
phenylalaninols,
this
work
contributes
to
expanding
library
demonstrates
substrate
scope
development
in
remote
reactions.
The Journal of Organic Chemistry,
Год журнала:
2022,
Номер
87(15), С. 9607 - 9618
Опубликована: Июль 14, 2022
A
palladium(II)-catalyzed
protocol
for
inactive
β-C(sp3)–H
bond
functionalization
has
been
first
accomplished.
The
reaction
proceeds
through
five-membered
carbocycles
the
formation
of
C–C
bonds
via
Pd(II)/Pd(IV)
cycle.
This
was
carried
out
with
various
aryl
iodides
and
benzothiazoles/benzoxazoles/benzimidazoles,
which
were
well-tolerated
in
this
successfully
generated
arylated
products.
Further
implementation
batch
to
continuous
flow
by
utilizing
a
PTFE
(polytetrafluoroethylene)
capillary
reactor
enhanced
efficiency
decreased
time
(18.4
min)
as
compared
conditions
(8
h).
Even
on
gram
scale,
process
produced
excellent
yield
negligible
diarylations.
Functional
group
tolerance,
continuous-flow
approach,
easy-to-handle
make
very
attractive.
Synthesis,
Год журнала:
2023,
Номер
55(24), С. 4113 - 4144
Опубликована: Авг. 2, 2023
Abstract
We
report
the
Pd(II)-catalyzed,
picolinamide-directed
δ-C(sp2)–H
(ortho)
functionalization
of
phenylalaninol
scaffolds.
Assembling
δ-C–H
arylated,
alkylated,
benzylated,
alkenylated,
brominated,
and
iodinated
scaffolds
was
accomplished.
The
arylation
reaction
occurred
under
neat
conditions.
Hydrolysis
picolinamide
moiety
synthetic
utility
arylated
substrates
were
explored.
have
also
shown
preparation
some
modified
Matijin–Su
(aurantiamide)
derivatives
using
bis
compounds
obtained
from
(Matijin–Su
is
an
anti-HBV
agent
possessing
unit).
Considering
importance
phenylalaninols,
this
work
contributes
to
expanding
library
demonstrates
substrate
scope
development
in
remote
reactions.
