A
novel
pyridyl-thiadiazole
ligand
has
been
designed,
synthesized,
and
employed
in
the
preparation
of
a
heterogeneous
iridium
catalyst
supported
on
multi-hydroxyl
polyhedral
oligomeric
silsesquioxane.
The
as-prepared
exhibits
excellent
catalytic
activity
one-pot
cascade
selective
synthesis
N-/C-substituted
indole
derivatives
from
amino
alcohols
via
borrowing
hydrogen
strategy.
Meanwhile,
it
was
observed
that
this
approach
good
functional
group
tolerance
broad
substrate
scope.
Notably,
by
employing
system,
an
inhibitor
against
gp41-mediated
HIV-1
fusion
core
structure
could
be
conveniently
synthesized
2-aminophenethyl
alcohol
benzyl
40.6%
total
yield
for
only
four
steps
“borrowing
hydrogen”
Mechanistic
explorations
showed
transformation
undergoes
processes,
involving
N/C-alkylation
through
strategy,
oxidative
cyclization.
Recycling
experiments
disclosed
easily
recovered
reused
at
least
seven
times
with
TON.
Organometallics,
Год журнала:
2024,
Номер
43(21), С. 2697 - 2702
Опубликована: Окт. 7, 2024
Recent
research
has
focused
a
lot
on
using
the
borrowing
hydrogen
(BH)
approach
to
react
amines
with
alcohols
convert
C–O
bond
into
C–N
bond.
However,
notion
of
chemoselectivity
in
BH-mediated
N-alkylation
rarely
been
studied.
Herein,
we
have
demonstrated
application
synthesized
SNS-Ni
complex
constructing
various
bonds
via
coupling
diverse
alcohols.
Delightfully,
catalytic
protocol
also
activates
challenging
C4–C16
aliphatic
Aryl
amino
are
selectively
N-alkylated
different
alcohols,
while
keeping
OH
group
intact
alcohol
portion.
Furthermore,
without
reducing
distal
unsaturation,
technique
was
successfully
employed
for
chemoselective
fatty
The
preliminary
mechanistic
investigation
suggests
alkylation
occurs
nonradical
pathway.
A
novel
pyridyl-thiadiazole
ligand
has
been
designed,
synthesized,
and
employed
in
the
preparation
of
a
heterogeneous
iridium
catalyst
supported
on
multi-hydroxyl
polyhedral
oligomeric
silsesquioxane.
The
as-prepared
exhibits
excellent
catalytic
activity
one-pot
cascade
selective
synthesis
N-/C-substituted
indole
derivatives
from
amino
alcohols
via
borrowing
hydrogen
strategy.
Meanwhile,
it
was
observed
that
this
approach
good
functional
group
tolerance
broad
substrate
scope.
Notably,
by
employing
system,
an
inhibitor
against
gp41-mediated
HIV-1
fusion
core
structure
could
be
conveniently
synthesized
2-aminophenethyl
alcohol
benzyl
40.6%
total
yield
for
only
four
steps
“borrowing
hydrogen”
Mechanistic
explorations
showed
transformation
undergoes
processes,
involving
N/C-alkylation
through
strategy,
oxidative
cyclization.
Recycling
experiments
disclosed
easily
recovered
reused
at
least
seven
times
with
TON.