The Journal of Organic Chemistry,
Journal Year:
2021,
Volume and Issue:
86(3), P. 2827 - 2839
Published: Jan. 20, 2021
A
protocol
for
the
preparation
of
7-amido
indoles
via
regioselective
C–H
bond
functionalization
has
been
first
accomplished
under
Ru(II)
catalysis.
Indole
derivatives
and
4-aryl/heteroaryl/benzyl/alkyl
dioxzaolines
containing
various
substituents
were
applicable
this
transformation,
readily
providing
amidated
in
moderate
to
good
yields.
This
novel
process
many
advantages,
including
compatibility
with
diverse
functional
groups,
broad
substrate
scopes,
mild
reaction
conditions.
Deuteration
studies
control
experiments
have
performed
understand
mechanism
transformation.
Angewandte Chemie International Edition,
Journal Year:
2020,
Volume and Issue:
60(13), P. 7066 - 7071
Published: Dec. 30, 2020
Abstract
The
use
of
an
operationally
convenient
and
stable
silicon
reagent
(octamethyl‐1,4‐dioxacyclohexasilane,
ODCS)
for
the
selective
silacyclization
(hetero)arenes
via
twofold
C−H
activation
is
reported.
This
method
compatible
with
N‐containing
heteroarenes
such
as
indoles
carbazoles
varying
complexity.
ODCS
can
also
be
utilized
other
types
substrates,
including
tertiary
phosphines
aryl
halides.
A
series
mechanistic
experiments
density
functional
theory
(DFT)
calculations
were
used
to
investigate
preferred
pathway
this
process.
ACS Catalysis,
Journal Year:
2021,
Volume and Issue:
11(9), P. 4929 - 4935
Published: April 8, 2021
Control
of
regioselectivity
that
defies
the
intrinsic
reactivity
arene
C–H
bonds
remains
a
formidable
challenge.
In
this
work,
dimeric
Rh(II)
complexes
have
been
applied
as
an
efficient
catalyst
for
regioselective
coupling
NH
indoles
with
diazo
compounds.
Two-substituted
mostly
reacted
C(6)
selectivity.
Mechanistic
studies
revealed
results
from
hydrogen-bonding
directing
effect,
and
C–C
bond
formation
proceeds
via
Friedel–Crafts-type
attack
indole
toward
carbene
species.
contrast,
reaction
4-methoxyindoles
occurred
exclusively
complementary
C(7)
Organic Letters,
Journal Year:
2023,
Volume and Issue:
25(14), P. 2456 - 2460
Published: March 31, 2023
Here,
we
report
a
novel
strategy
for
constructing
maleimide-containing
peptides
and
cyclic
using
Rh(III)-catalyzed
tryptophan
(Trp)
(C7)
alkenylation,
which
is
challenging
due
to
the
inherent
reactivity
of
indole
benzenoid
ring.
This
method
scalable
exhibits
broad
substrate
scope.
The
utility
this
protocol
could
further
be
demonstrated
by
synthesis
peptide
conjugates
with
natural
products
amino
acids
as
well
construction
maleimide-braced
peptides.
Journal of Heterocyclic Chemistry,
Journal Year:
2025,
Volume and Issue:
unknown
Published: Jan. 27, 2025
ABSTRACT
An
efficient
method
for
the
synthesis
of
valuable
terminal
C7‐alkenylated
indolines
through
direct
C–H
alkenylation
N
‐pyridinyl
in
presence
a
rhodium
catalyst
has
been
developed.
Alkenyl
borates
were
first
used
as
useful
alkenyl
reagent
functionalization
indolines.
Under
mild
reaction
conditions,
series
with
different
functional
groups
compatible
this
transformation,
affording
product
good
to
excellent
yields.
Moreover,
indoline
can
be
conveniently
converted
pyrroloquinoline
derivative,
which
is
popular
tricyclic
skeleton
bioactive
compounds,
highlighting
its
potential
application
value.
The Journal of Organic Chemistry,
Journal Year:
2021,
Volume and Issue:
86(3), P. 2827 - 2839
Published: Jan. 20, 2021
A
protocol
for
the
preparation
of
7-amido
indoles
via
regioselective
C–H
bond
functionalization
has
been
first
accomplished
under
Ru(II)
catalysis.
Indole
derivatives
and
4-aryl/heteroaryl/benzyl/alkyl
dioxzaolines
containing
various
substituents
were
applicable
this
transformation,
readily
providing
amidated
in
moderate
to
good
yields.
This
novel
process
many
advantages,
including
compatibility
with
diverse
functional
groups,
broad
substrate
scopes,
mild
reaction
conditions.
Deuteration
studies
control
experiments
have
performed
understand
mechanism
transformation.
