Organic Letters,
Год журнала:
2024,
Номер
26(43), С. 9401 - 9406
Опубликована: Окт. 22, 2024
An
operationally
simple
and
highly
efficient
synthesis
of
functionalized
thiophenes
has
been
developed
by
LiBr
promoted
heteroannulation
β-ketodithioesters
thioamides
with
bench-stable
sulfoxonium
ylides
in
open
air
for
the
first
time.
This
one-pot
strategy
involves
formal
Csp3–H
bond
insertion/intramolecular
cyclization
cascade,
featuring
readily
accessible
starting
materials,
TM
additive-free
condition,
broad
substrate
scope,
high
functional
group
compatibility,
scalability.
Moreover,
carbonyl,
thiomethyl,
amino
groups
resulting
thiophene
provide
a
good
handle
on
downstream
transformations.
Research Square (Research Square),
Год журнала:
2024,
Номер
unknown
Опубликована: Июль 24, 2024
Abstract
Although
the
directing
group
assisted
ortho-B
−
H
activation
reactions
of
o-carboranes
have
been
well
established
during
past
decade,
meta-B
are
unexplored
so
far.
Herein,
iridium(III)-catalyzed
remote
B(9)
alkylation
with
nitrile
template
demonstrated
for
first
time.
It
was
revealed
that
fine
tuning
structures
is
essential
high
reaction
efficiency
and
regioselectivity.
This
process
exhibits
a
broad
substrate
scope
good
functional
tolerance
under
simple
conditions.
The
template,
readily
accessible
from
o-carborane
acids,
can
be
removed
conveniently
after
completion
reaction.
present
method
provides
powerful
synthetic
route
to
complex
derivatives,
demonstrating
successful
larger
scale
further
molecular
transformations
B(9)-alkylated
products.
Organic Letters,
Год журнала:
2024,
Номер
26(43), С. 9401 - 9406
Опубликована: Окт. 22, 2024
An
operationally
simple
and
highly
efficient
synthesis
of
functionalized
thiophenes
has
been
developed
by
LiBr
promoted
heteroannulation
β-ketodithioesters
thioamides
with
bench-stable
sulfoxonium
ylides
in
open
air
for
the
first
time.
This
one-pot
strategy
involves
formal
Csp3–H
bond
insertion/intramolecular
cyclization
cascade,
featuring
readily
accessible
starting
materials,
TM
additive-free
condition,
broad
substrate
scope,
high
functional
group
compatibility,
scalability.
Moreover,
carbonyl,
thiomethyl,
amino
groups
resulting
thiophene
provide
a
good
handle
on
downstream
transformations.
