Benzylic C(sp3)–H Functionalization via Copper-Catalyzed [3+3] Radical Cycloaddition
Jun Shi,
Xiong-Jiang Li,
Shu-Yun Jiang
и другие.
ACS Catalysis,
Год журнала:
2024,
Номер
14(8), С. 5605 - 5611
Опубликована: Март 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.
Язык: Английский
Copper/Iodine Co-catalyzed Oxygenative Transannulation of Tryptamines Enables Direct Synthesis of Donaxaridine and Its Derivatives
Yan-Zheng Sun,
Ying-Ai Wu,
Jun Shi
и другие.
Organic Letters,
Год журнала:
2024,
Номер
26(3), С. 625 - 630
Опубликована: Янв. 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.
Язык: Английский
Lewis-Base-Catalyzed Asymmetric Allylation of Isatins with Allyltrichlorosilane
Yasemin Özkaya,
Frederic Ballaschk,
Christian Wagner
и другие.
Organic Letters,
Год журнала:
2025,
Номер
unknown
Опубликована: Март 12, 2025
Herein
we
report
the
enantioselective
synthesis
of
3-allyl-3-hydroxyoxindoles,
a
core
scaffold
in
wide
range
bioactive
molecules,
using
Lewis-base
catalyst
and
readily
abundant
inexpensive
allyltrichlorosilane.
This
transition-metal-free
protocol
employs
relatively
low
loadings
privileged
bispyrrolidine-type
to
achieve
high
yields
enantioselectivities
(up
98%
yield
98:2
er).
The
total
syntheses
natural
products
(−)-flustraminol
B
(−)-chimonamidine
were
also
successfully
carried
out
our
newly
developed
method
as
key
step,
highlighting
potential
this
for
efficient
precise
complex
products.
Язык: Английский
Asymmetric Cascade Dearomatization–Cyclization Reaction of Tryptamines with β,γ-Alkynyl-α-imino Esters: Access to Hexahydropyrrolo[2,3-b]indole-Containing Tetrasubstituted α-Amino Allenoates
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(14), С. 10148 - 10162
Опубликована: Июль 3, 2024
An
organocatalytic
enantio-
and
diastereoselective
synthesis
of
hexahydropyrrolo[2,3-
Язык: Английский
Copper‐Catalyzed Tunable Oxygenative Rearrangement of Tetrahydrocarbazoles
Chemistry - A European Journal,
Год журнала:
2024,
Номер
30(44)
Опубликована: Июнь 3, 2024
Herein,
we
report
a
general
copper-catalyzed
method
for
the
tunable
oxygenative
rearrangement
of
tetrahydrocarbazoles
to
cyclopentyl-bearing
spiroindolin-2-ones
and
spiroindolin-3-ones.
The
demonstrates
excellent
chemoselectivity,
regioselectivity,
product
control
simply
by
using
H
Язык: Английский
Direct Synthesis of N-Fused Indoles Enabled by Copper-Catalyzed Aerobic Oxygenative Rearrangement
ACS Catalysis,
Год журнала:
2024,
Номер
14(22)
Опубликована: Ноя. 4, 2024
N-Fused
indoles
are
typical
N-heterocycles,
which
extensively
found
in
natural
products
and
bioactive
molecules.
Despite
their
importance,
the
synthesis
of
N-fused
has
not
yet
been
fully
developed.
Herein,
we
report
a
direct,
general
unified
copper-catalyzed
aerobic
oxygenative
skeletal
rearrangement
strategy
using
readily
available
cyclic
indole
substrates,
provides
practical
synthetic
platform
for
rapid
construction
wide
array
scaffolds.
This
open-flask
method
features
mild
reaction
conditions,
high
chemoselectivity,
broad
substrate
scope
(over
90
examples).
The
scaled-up
versatile
transformations
various
nucleophiles
demonstrated
scalability
utility
this
protocol.
Mechanistic
studies
revealed
that,
by
involving
unique
single-electron
transfer
(SET)-induced
oxygenation
mechanism,
tetrahydro-γ-carbolines
proceeded
via
formal
1,3-migration
rearrangement,
while
that
tetrahydrocarbazoles
Witkop–Winterfeldt/C–C
cleavage
cascade.
Язык: Английский