Journal of the American Chemical Society,
Journal Year:
2021,
Volume and Issue:
143(33), P. 12961 - 12967
Published: Aug. 12, 2021
Catalytic
asymmetric
dicarbofunctionalization
of
tethered
alkenes
has
emerged
as
a
promising
tool
for
producing
chiral
cyclic
molecules;
however,
it
typically
relies
on
aryl-tethered
to
form
benzene-fused
compounds.
Herein,
we
report
an
enantioselective
cross-electrophile
divinylation
reaction
nonaromatic
substrates,
2-bromo-1,6-dienes.
The
approach
thus
offers
route
new
architectures,
which
are
key
structural
motifs
found
in
various
biologically
active
proceeds
under
mild
conditions,
and
the
use
t-Bu-pmrox
3,5-difluoro-pyrox
ligands
resulted
formation
divinylated
products
with
high
chemo-,
regio-,
enantioselectivity.
method
is
applicable
incorporation
hetero-
carbocycles
into
complex
molecules.
ACS Catalysis,
Journal Year:
2019,
Volume and Issue:
9(8), P. 7335 - 7342
Published: July 17, 2019
Transition-metal-catalytic
domino
reactions
represent
important
advances
in
synthetic
organic
chemistry.
Their
development
benefits
synthesis
by
providing
highly
efficient
and
step-economical
methods
to
complex
molecules
with
impressive
selectivity.
Herein,
a
Ni-catalyzed
reductive
cyclization
of
acrylamides
alkynyl
bromides
is
reported,
enabling
rapid
assembly
range
substituted
2,3-fused
cyclopentannulated
indolines.
Preliminary
mechanistic
studies
revealed
that
tricyclic
indolines
are
afforded
through
regioselective
migratory
insertion
1,3-diynes,
which
formed
from
the
homocoupling
bromides,
into
situ
generated
σ-alkyl-Ni(II)
species,
followed
nucleophilic
addition
resulting
alkenyl
nickel
unactivated
amides.
Most
importantly,
regio-
enantioselective
internal
alkynes
has
also
been
developed.
This
transformation
takes
place
under
mild
conditions
high
efficiency,
access
structurally
diverse
synthetically
useful
yields
regioselectivity
(>20/1)
enantioselectivity
(27
examples,
82–96%
ee).
Angewandte Chemie International Edition,
Journal Year:
2020,
Volume and Issue:
60(4), P. 1861 - 1868
Published: Oct. 20, 2020
Abstract
A
cobalt‐promoted
electrochemical
1,2‐diarylation
of
alkenes
with
electron‐rich
aromatic
hydrocarbons
via
direct
dual
C−H
functionalizations
is
described,
which
employs
a
radical
relay
strategy
to
produce
polyaryl‐functionalized
alkanes.
Simply
by
using
graphite
rod
cathode
instead
platinum
plate
cathode,
chemoselectivity
this
shifted
the
dehydrogenative
[2+2+2]
cycloaddition
1,2‐diarylation,
annulation,
and
dehydrogenation
cascades
leading
complex
11,12‐dihydroindolo[2,3‐
]carbazoles.
Mechanistical
studies
indicate
that
key
step
for
processes
transformations
aryl
sp
2
‐hybridized
carbon‐centered
radicals
deprotonation
corresponding
cation
intermediates
bases.
ACS Catalysis,
Journal Year:
2021,
Volume and Issue:
11(8), P. 4576 - 4582
Published: March 31, 2021
Reported
herein
is
the
gold-catalyzed
1,2-aminoarylation
of
alkenes
that
engages
external
amine
as
a
coupling
partner.
Careful
optimization
studies
revealed
significant
role
concentration
base
to
achieve
highly
chemoselective
access
aminoarylation
products
over
potential
C–N
cross-coupled
products.
Overcoming
all
limitations,
current
strategy
provided
straightforward
medicinally
relevant
3-aminochroman,
2-aminotetrahydronaphthalene,
and
2-aminoindane
derivatives.
Journal of the American Chemical Society,
Journal Year:
2021,
Volume and Issue:
143(33), P. 12961 - 12967
Published: Aug. 12, 2021
Catalytic
asymmetric
dicarbofunctionalization
of
tethered
alkenes
has
emerged
as
a
promising
tool
for
producing
chiral
cyclic
molecules;
however,
it
typically
relies
on
aryl-tethered
to
form
benzene-fused
compounds.
Herein,
we
report
an
enantioselective
cross-electrophile
divinylation
reaction
nonaromatic
substrates,
2-bromo-1,6-dienes.
The
approach
thus
offers
route
new
architectures,
which
are
key
structural
motifs
found
in
various
biologically
active
proceeds
under
mild
conditions,
and
the
use
t-Bu-pmrox
3,5-difluoro-pyrox
ligands
resulted
formation
divinylated
products
with
high
chemo-,
regio-,
enantioselectivity.
method
is
applicable
incorporation
hetero-
carbocycles
into
complex
molecules.
