Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(20), P. 4262 - 4267
Published: May 9, 2024
A
novel
Pd-catalyzed
three-component
domino
reaction
for
the
stereoselective
synthesis
of
highly
functionalized
allyl
cinnamates
has
been
developed.
In
this
protocol,
a
sequential
process
C–C
bond
activation
and
intermolecular
allylic
substitution
was
well-organized.
The
key
transformation
is
in
situ
generated
hydrolysis
product
cyclopropenone,
which
triggered
new
with
vinylethylene
carbonates.
mechanism
investigated,
demonstrating
high
stereoselectivity
excellent
atomic
economy
process.
Organic Letters,
Journal Year:
2021,
Volume and Issue:
23(16), P. 6466 - 6470
Published: Aug. 3, 2021
We
disclose
a
Ni-catalyzed
reductive
arylcyanation
of
alkene
using
environmentally
benign
and
nontoxic
organo
cyanating
reagent
N-cyano-N-phenyl-p-toluenesulfonamide.
This
reaction
provides
new
method
for
the
rapid
synthesis
cyano-substituted
oxindoles
isoquinoline-1,3-diones
features
high
functional
group
tolerance.
In
addition,
an
enantioselective
version
was
developed
construction
enantiomerically
enriched
3-cyanomethyl
oxindole.
has
also
been
applied
to
natural
alkaloids
(+)-esermethole
(+)-physostigmine.
Organic Letters,
Journal Year:
2021,
Volume and Issue:
23(16), P. 6407 - 6411
Published: Aug. 4, 2021
Herein
we
report
a
nickel-catalyzed
asymmetric
reductive
dicarbamoylation
of
alkenes,
in
which
tethered
carbamoyl
chlorides
and
isocyanates
serve
as
distinct
electrophilic
carbamoylating
agents,
providing
new
access
to
chiral
oxindoles
bearing
an
amide-substituted
quaternary
stereogenic
center.
ACS Catalysis,
Journal Year:
2022,
Volume and Issue:
12(16), P. 10039 - 10046
Published: Aug. 3, 2022
We
have
developed
an
allylic
alkylation
of
alkanes
by
dual
photo-HAT/nickel
catalysis.
In
this
reaction,
radical-type
hydrogen-atom-transfer
the
is
enabled
decatungstate
as
a
photocatalyst,
whereas
nickel
serves
to
cleave
C–O
bond
in
substrates
under
mild
reaction
conditions.
This
co-catalyzed
provides
method
for
direct
functionalization
alkanes.
Density
functional
theory
calculations
show
that
reductive
elimination
rate-determining
step
reaction.
ACS Catalysis,
Journal Year:
2023,
Volume and Issue:
13(3), P. 2156 - 2161
Published: Jan. 25, 2023
The
asymmetric
allylic
alkylation
(AAA)
reaction
using
less
reactive,
stable
sources
is
challenging.
We
achieved
a
nickel(0)-catalyzed
AAA
of
β-dicarbonyl
compounds
under
ambient
conditions
through
unstrained
C–C
bond
activation
2-allylated
2-methylcyclohexane-1,3-dione
derivatives
to
afford
the
corresponding
quaternary
chiral
in
high
yield
with
enantioselectivity.
proceeded
almost
irreversibly
due
low
solubility
side-product,
2-methylcyclohexane-1,3-dione.
Control
experiments
and
DFT
calculations
allowed
for
elucidating
mechanism
Ni(0)-(S)-tol-MeO-BIPHEP
catalyst
system;
turnover
limiting
step
formation,
reverse
requires
7.6
kcal
mol–1
higher
energy
than
forward
reaction.
Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(20), P. 4262 - 4267
Published: May 9, 2024
A
novel
Pd-catalyzed
three-component
domino
reaction
for
the
stereoselective
synthesis
of
highly
functionalized
allyl
cinnamates
has
been
developed.
In
this
protocol,
a
sequential
process
C–C
bond
activation
and
intermolecular
allylic
substitution
was
well-organized.
The
key
transformation
is
in
situ
generated
hydrolysis
product
cyclopropenone,
which
triggered
new
with
vinylethylene
carbonates.
mechanism
investigated,
demonstrating
high
stereoselectivity
excellent
atomic
economy
process.
