Authorea (Authorea),
Год журнала:
2024,
Номер
unknown
Опубликована: Янв. 30, 2024
An
elegant
Pd(dba)2-catalyzed
enantioselective
Heck
dearomative
annulation
of
indoles
and
N-tosylhydrazones
for
the
straightforward
assembly
structurally
diverse
optically
active
indoline
scaffolds
containing
quaternary
carbon
centers
at
C2-position
has
been
developed.
The
tandem
protocol,
which
utilized
Pd(dba)2/BINOL-based
phosphoramidite
ligand
as
catalytic
system,
proceeded
smoothly
through
successive
oxidative
addition,
intramolecular
palladation,
migratory
insertion,
reductive
elimination
se-quences,
leading
to
chiral
derivatives
in
moderate
excellent
yields,
with
enantioselectivities
diastereoselec-tivities.
In
synthetic
practicability
system
was
underlined
by
a
scaled-up
experiment
late-stage
derivatization
products,
thus
highlighting
potential
applications
chemistry,
medicinal
material
science.
The Journal of Organic Chemistry,
Год журнала:
2022,
Номер
87(16), С. 10917 - 10927
Опубликована: Авг. 10, 2022
An
elegant
Pd-catalyzed
intramolecular
Heck
dearomative
alkenylation
of
aryl
iodides
with
functionalized
N-tosylhydrazones
proceeded
through
a
sequential
carbopalladation,
migratory
insertion,
and
β-hydride
elimination
in
the
presence
Pd(CF3COO)2
(10
mol
%),
PPh3
(30
Cs2CO3
(2.0
equiv)
1,4-dioxane
mL)
at
120
°C
for
14
h
under
an
argon
atmosphere.
This
cascade
cycloaddition
protocol
provided
reliable
versatile
approach
to
sequence
structurally
diverse
indolines
moderate
good
yields
functional
group
compatibility.
In
addition,
synthetic
robustness
methodology
is
highlighted
by
scaled-up
experiment
derivatization
products
via
epoxidation
reduction
reactions.
Organic Chemistry Frontiers,
Год журнала:
2023,
Номер
10(14), С. 3504 - 3508
Опубликована: Янв. 1, 2023
The
first
palladium-catalyzed
cascade
reaction
combining
Pd(
ii
)-catalyzed
nucleophilic
cyclization
of
alkynes
and
intramolecular
redox-relay
Heck
arylation
alkenols
has
been
developed.
Current Organic Chemistry,
Год журнала:
2023,
Номер
27(2), С. 71 - 92
Опубликована: Янв. 1, 2023
Abstract:
This
review
updates
the
field
of
asymmetric
cascade
palladium
catalysis
applied
to
synthesis
chiral
heterocycles
since
2019.
It
illustrates
how
much
a
diversity
catalysts
promote
unprecedented
domino
reactions
many
types,
allowing
direct
access
wide
variety
complex
and
densely
functionalized
heterocyclic
molecules.
Angewandte Chemie,
Год журнала:
2022,
Номер
134(13)
Опубликована: Янв. 26, 2022
Abstract
Dearomatized
indole
derivatives
bearing
a
C3‐
or
C2‐stereocenter
exist
ubiquitously
in
natural
products
and
biologically
active
molecules.
Despite
remarkable
advances
their
synthesis,
stereoselective
regio‐divergent
methods
are
still
high
demand.
Herein,
Pd‐catalyzed
intermolecular
asymmetric
spiroannulation
of
2,3‐disubstituted
indoles
with
internal
alkynes
has
been
developed
for
the
efficient
construction
indoline
structures
C2‐quaternary
stereocenter.
Stereospecific
aza‐semipinacol
rearrangement
these
under
acidic
conditions
afforded
indolenine
C3‐quaternary
stereocenter,
where
migrating
group
could
be
controlled
by
reaction
sequence.
The
together
subsequent
enabled
divergent
access
to
dearomatized
either
Authorea (Authorea),
Год журнала:
2024,
Номер
unknown
Опубликована: Янв. 30, 2024
An
elegant
Pd(dba)2-catalyzed
enantioselective
Heck
dearomative
annulation
of
indoles
and
N-tosylhydrazones
for
the
straightforward
assembly
structurally
diverse
optically
active
indoline
scaffolds
containing
quaternary
carbon
centers
at
C2-position
has
been
developed.
The
tandem
protocol,
which
utilized
Pd(dba)2/BINOL-based
phosphoramidite
ligand
as
catalytic
system,
proceeded
smoothly
through
successive
oxidative
addition,
intramolecular
palladation,
migratory
insertion,
reductive
elimination
se-quences,
leading
to
chiral
derivatives
in
moderate
excellent
yields,
with
enantioselectivities
diastereoselec-tivities.
In
synthetic
practicability
system
was
underlined
by
a
scaled-up
experiment
late-stage
derivatization
products,
thus
highlighting
potential
applications
chemistry,
medicinal
material
science.
