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.
Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(2), P. 467 - 472
Published: Jan. 5, 2024
Disclosed
here
is
a
visible-light
photoredox-catalyzed
intermolecular
sequential
α-aminomethyl/carboxylative
dearomatization
of
indoles
with
CO2
and
α-aminoalkyl
radical
precursors,
affording
series
functionalized
indoline-3-carboxylic
acids
lactams
in
good
yields
high
regioselectivity.
This
multicomponent
reaction
provides
green
facile
method
for
the
synthesis
diverse
indolines
by
using
as
carboxylic
carbonyl
source.
Journal of the American Chemical Society,
Journal Year:
2024,
Volume and Issue:
146(30), P. 20904 - 20912
Published: July 20, 2024
Although
divalent
Sm
reagents
are
some
of
the
most
important
single-electron
transfer
for
reductive
transformations,
their
catalytic
applications
challenging.
In
this
study,
a
bidentate
phosphine
oxide
ligand
substituted
with
9,10-diphenylanthracene
as
visible-light
antenna
was
designed
Sm-catalyzed
reduction
reactions
under
mild
reaction
conditions.
Pinacol
coupling
aryl
ketones
and
aldehydes
developed
1
mol
%
catalyst
organic
amine
(DIPEA)
sacrificial
reductant.
Mechanistic
studies
suggest
that
visible-light-antenna
coordinates
to
Sm(III)
reduces
Sm(II)
irradiation.
The
system
is
also
applicable
cross-pinacol
other
including
aza-pinacol
coupling,
flavone
dimerization,
C-O
bond
cleavage,
C-C
ring-opening
cyclopropane,
ketyl-olefin
cross-coupling
ketyl
radical
α-amino
radical.
Chemical Science,
Journal Year:
2024,
Volume and Issue:
15(11), P. 4114 - 4120
Published: Jan. 1, 2024
Starting
from
the
same
substrates,
tunable
C–H
functionalization
and
dearomatization
have
been
achieved
under
catalysis
of
a
new
organic
photocatalyst
–
isoazatruxene
ITN-2.
Molbank,
Journal Year:
2025,
Volume and Issue:
2025(1), P. M1962 - M1962
Published: Feb. 5, 2025
(1S,1′S)-2,2′-(Benzylazanediyl)bis(1-((3aR,4R,6aR)-2,2-dimethyltetrahydrofuro
[3,4
d][1,3]dioxol-4-yl)ethan-1-ol),
presenting
a
tertiary
β-aminodiol
moiety,
was
synthesized
in
72%
yield
one-step
reaction
from
an
aminolysis
of
isosorbide-derived
oxirane
with
benzylamine.
This
fully
characterized
by
1H
and
13C
NMR
HRMS
analyses.
Angewandte Chemie International Edition,
Journal Year:
2023,
Volume and Issue:
62(51)
Published: Nov. 11, 2023
Herein,
we
report
an
unprecedented
skeletal
rearrangement
reaction
of
tetrahydro-β-carbolines
enabled
by
copper-catalyzed
single-electron
oxidative
oxygenation,
in
which
H2
O
and
O2
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.
Research Square (Research Square),
Journal Year:
2024,
Volume and Issue:
unknown
Published: March 8, 2024
Abstract
Heterocycle
skeletal
editing
has
recently
experienced
a
renaissance
in
chemical
synthesis
by
offering
simple
retrosynthetic
disconnection
between
complex
structural
scaffolds
and
starting
materials.
However,
asymmetric
dearomatization
of
heteroarenes
through
single
atom
“cut
paste”
remains
unknown
to
date.
Herein,
we
report
the
first
enantiodivergent
dearomative
indoles
via
single-carbon-atom
insertion
using
trifluoromethyl
N
-triftosylhydrazones
as
carbene
precursors.
This
strategy
provides
straightforward
methodology
access
both
enantiomers
3,4-dihydroquinolines
containing
trifluoromethylated
quaternary
stereocenter
switching
chirality
catalyst.
The
synthetic
utility
nature
this
were
demonstrated
scope
evaluation,
product
derivatization,
short
drug
analogues.
Mechanistic
studies
disclose
that
selectivity
induction
are
under
catalyst
control
during
initial
cyclopropanation
step.
