Angewandte Chemie,
Journal Year:
2023,
Volume and Issue:
135(51)
Published: Nov. 11, 2023
Abstract
Herein,
we
report
an
unprecedented
skeletal
rearrangement
reaction
of
tetrahydro‐
β
‐carbolines
enabled
by
copper‐catalyzed
single‐electron
oxidative
oxygenation,
in
which
H
2
O
and
act
as
oxygen
sources
to
generate
a
unique
2‐hydroxyl‐3‐peroxide
indoline
intermediate.
The
synthetic
reactivity
species
was
demonstrated
multi‐step
bond
cleavage
formation
cascade.
Using
readily
available
copper
catalyst
under
open‐air
conditions,
highly
important
yet
synthetically
difficult
spiro[pyrrolidone‐(3,1‐benzoxazine)]
products
were
obtained
single
operation.
utility
this
methodology
is
the
efficient
synthesis
natural
donaxanine
chimonamidine,
well
3‐hydroxyl‐pyrroloindoline
scaffold,
just
one
or
two
steps.
Journal of the American Chemical Society,
Journal Year:
2024,
Volume and Issue:
146(4), P. 2325 - 2332
Published: Jan. 17, 2024
The
only
known
method
for
the
dearomative
trifluoromethoxylation
of
indoles
is
preliminary,
with
one
substrate
successfully
undergoing
reaction.
In
this
study,
we
not
developed
a
broadly
applicable
indole
but
also
achieved
divergent
by
fine-tuning
reaction
conditions.
Under
optimized
conditions,
silver
salt
and
an
easily
handled
OCF3
reagent,
various
smoothly
underwent
dearomatization
to
afford
diverse
array
ditrifluoromethoxylated
indolines
in
50–84%
isolated
yields
up
37:1
diastereoselectivity,
fluorinated
trifluoromethoxylated
were
obtained
exclusive
trans
selectivity.
addition,
conditions
compatible
other
heteroaromatic
rings
as
well
styrene
moieties.
ACS Catalysis,
Journal Year:
2024,
Volume and Issue:
14(8), P. 5605 - 5611
Published: March 29, 2024
The
development
of
benzylic
C(sp3)–H
functionalization
methods
for
the
assembly
derivatives
has
been
extensively
explored
in
recent
years.
However,
engagement
carbon
and
its
adjacent
C=C
bond
as
a
C3
synthon
cycloaddition
reaction
via
direct
C–H
activation
is
rare.
Herein,
we
report
copper-catalyzed
[3+3]
radical
through
to
construct
six-membered
cyclohexane-type
rings.
In
this
reaction,
2-benzylic
an
indole
selectively
activated
serves
that
reacts
highly
chemoselective
intermolecular
self-[3+3]
cross-[3+3]
pathways.
Multiple
symmetric
nonsymmetric
polycyclic
hexahydrocarbazole
scaffolds
with
hexacyclic
6/5/5/6/5/5/6
pentacyclic
6/5/5/6/5/6
ring
systems
are
synthesized
high
efficiency
chemoselectivity
using
strategy.
Inspired
by
unique
addition
pathway
cycloaddition,
controllable
construction
C3a-alkylated
pyrroloindolines
was
also
developed.
Journal of the American Chemical Society,
Journal Year:
2023,
Volume and Issue:
145(40), P. 21745 - 21751
Published: Sept. 27, 2023
Reactions
capable
of
transposing
the
oxidation
levels
adjacent
carbon
atoms
enable
rapid
and
fundamental
alteration
a
molecule's
reactivity.
Herein,
we
report
1,2-transposition
atom
level
in
cyclic
acyclic
tertiary
amides,
resulting
one-pot
synthesis
1,2-
1,3-oxygenated
amines.
This
transfer
was
facilitated
by
careful
orchestration
an
iridium-catalyzed
reduction
with
functionalization
transiently
formed
enamine
intermediates.
A
novel
1,2-carbonyl
transposition
is
described,
breadth
this
redox
strategy
has
been
further
explored
development
aminoalcohol
enaminone
syntheses.
The
diverse
β-functionalized
amine
products
were
shown
to
be
multifaceted
valuable
synthetic
intermediates,
accessing
challenging
biologically
relevant
motifs.
Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(3), P. 625 - 630
Published: Jan. 11, 2024
We
report
a
general
copper/iodine
co-catalyzed
oxygenative
transannulation
strategy
using
readily
available
tryptamines.
Molecular
oxygen
and
water
are
used
as
sources
provide
direct
access
to
the
donaxaridine
scaffold
its
derivatives.
This
methodology
is
applied
efficient
synthesis
of
natural
products
donaxaridine,
chimonamidine,
donaxanine,
donaxarine,
aline
in
just
one
or
two
steps.
The
tryptamines,
albeit
with
oxy-sensitive
dialkyl
N-H
groups,
selectively
oxidized
through
single-electron
transfer
dioxygenation
process.
Journal of Materials Chemistry A,
Journal Year:
2024,
Volume and Issue:
12(9), P. 5520 - 5529
Published: Jan. 1, 2024
6-Bromoxoindole,
an
electrolyte
additive,
enables
the
lithium–sulfur
battery
to
operate
stably
under
high-loading,
lean-electrolyte,
and
low-temperature
conditions
simultaneously.
Organic Letters,
Journal Year:
2025,
Volume and Issue:
unknown
Published: April 9, 2025
A
Rh(III)-catalyzed
dearomative
C3
alkoxylation
of
indoles
via
cascade
C(sp2)-H
activation
and
1,2-alkoxyl
shift
rearrangement
has
been
developed.
This
method
provides
an
efficient
strategy
to
rapidly
assemble
3-alkoxyindolin-2-one
scaffolds
using
alcohols
as
alkoxyl
sources.
Mechanistic
studies
indicate
that
indolyl
C2
followed
by
Ag(I)/Cu(II)-mediated
migration
is
involved
in
this
transformation.
Organic Letters,
Journal Year:
2025,
Volume and Issue:
unknown
Published: April 24, 2025
A
novel
Ru(II)-catalyzed
domino
reaction,
comprising
alkylation,
cyclization,
and
oxidation
of
2-aminophenethanols
with
benzyl
alcohols,
has
been
developed
for
the
synthesis
3-hydroxyindolin-2-ones.
This
transformation
exhibits
excellent
synthetic
efficiency,
enabling
selective
formation
four
or
three
σ
bonds,
one
π
bond,
quaternary
carbon
center
in
step
under
identical
conditions.
Furthermore,
it
provides
a
versatile
approach
to
3-hydroxyindolin-2-one
frameworks
distinct
substituents
at
1-
3-positions.
