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.
Organic Letters,
Год журнала:
2024,
Номер
26(18), С. 3739 - 3743
Опубликована: Апрель 29, 2024
An
enantioselective
Pd-catalyzed
intramolecular
dearomative
reductive
Heck
reaction
of
N-(o-bromoaryl)
indole-3-carboxamide
is
developed.
By
employing
Pd(dba)2/SPINOL-based
phosphoramidite
as
the
chiral
catalyst
and
HCO2Na
hydride
source,
a
series
enantioenriched
spiro
indolines
bearing
vicinal
stereocenters
were
afforded
in
moderate
to
good
yields
with
excellent
enantioselectivities.
The
formal
tetrasubstituted
alkene
β-hydrogens
therefore
realized
by
inhibiting
β-H
elimination.
Organic Letters,
Год журнала:
2024,
Номер
26(43), С. 9389 - 9394
Опубликована: Окт. 21, 2024
Until
now,
palladium-catalyzed
dearomative
Heck
reactions
of
indoles
were
largely
limited
to
β-H
elimination
and
nucleophilic
capture
the
transient
alkyl-Pd(II)
species.
Herein,
we
disclose
a
novel
Heck/C(sp
A
palladium-catalyzed
reaction
of
indoles
with
cyanoacetate
salts
enables
the
synthesis
2,6-disubstituted
indolines
via
tandem
dearomatization/decarboxylative
cyanomethylation.
Remarkably,
this
is
first
example
indole
difunctionalization
at
C2
and
C6
positions.
Moreover,
methodology
extends
to
cyclization/decarboxylative
cyanomethylation
aryl
halide-tethered
alkenes.
Chinese Journal of Organic Chemistry,
Год журнала:
2023,
Номер
43(4), С. 1271 - 1271
Опубликована: Янв. 1, 2023
Indolines
are
prevalent
scaffolds
of
numerous
natural
products,
pharmaceutical
agents,
and
bioactive
molecules,
therefore,
various
strategies
have
been
developed
to
access
indolines.Indole
dearomatization
has
recognized
as
an
important
straightforward
strategy
for
constructing
diverse
functionalized
indolines.Among
a
multitude
indoles
dearomatization,
the
well-known
relied
on
inherent
nucleophilicity
indole,
while
migratory
insertion
widely
applied
in
recent
years.Herein,
advances
Pd,
Ni,
Co,
Cu-catalyzed
tandem
dearomatizations
via
radical-mediated
process
summarized
detailedly,
mechanism
development
tendency
this
reactions
discussed.
Organic Letters,
Год журнала:
2022,
Номер
24(21), С. 3823 - 3827
Опубликована: Май 23, 2022
The
diastereoselective
synthesis
of
sulfonylated
indolines
is
reported.
A
palladium-catalyzed
dearomative
sulfination
(aza)indole-tethered
aryl
iodides
generates
reactive
benzylic
sulfinates.
These
intermediates
react
with
electrophiles
in
a
one-pot,
two-step
process
to
generate
products
good
yields
and
excellent
diastereoselectivity.
This
three-component
sequence
demonstrates
scalability
can
be
applied
toward
the
sulfonamides.
Additionally,
further
derivatizations
iodide
containing
furnish
spiro-
alkynylated
indoline
products.
The Journal of Organic Chemistry,
Год журнала:
2023,
Номер
88(22), С. 15881 - 15893
Опубликована: Ноя. 3, 2023
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
a
Pd(dba)2/BINOL-based
phosphoramidite
ligand
as
catalytic
system,
proceeded
smoothly
through
successive
oxidative
addition,
intramolecular
palladation,
migratory
insertion,
β-elimination
sequences,
leading
to
chiral
derivatives
in
moderate
excellent
yields,
with
enantioselectivities
diastereoselectivities.
In
synthetic
practicability
system
was
underlined
by
scaled-up
experiment
late-stage
derivatization
products,
thus
highlighting
potential
applications
chemistry,
medicinal
material
science.
Organic Chemistry Frontiers,
Год журнала:
2023,
Номер
10(23), С. 5940 - 5949
Опубликована: Янв. 1, 2023
Herein,
we
report
an
asymmetric
dearomative
reductive
arylallylation
of
indoles
with
trifluoromethyl
alkenes
enabled
by
nickel
catalysis
to
access
structurally
diverse
gem
-difluorovinyl-containing
chiral
polycyclic
indolines.
Organic & Biomolecular Chemistry,
Год журнала:
2024,
Номер
22(30), С. 6085 - 6089
Опубликована: Янв. 1, 2024
An
enantioselective
Cu-catalyzed
1,2-arylboration
reaction
of
N
-(
o
-iodobenzoyl)enamines
with
bis(pinacolato)diboron
(B
2
pin
)
is
developed
to
access
chiral
borate-containing
3,3′-disubstituted
isoindolinones.
