Angewandte Chemie International Edition,
Journal Year:
2024,
Volume and Issue:
64(1)
Published: Sept. 10, 2024
Different
from
the
reported
work
focusing
on
construction
of
single
P-
or
C-stereocenter
via
hydrophosphinylation
unsaturated
carbon
bonds,
highly
diastereo-
and
enantioselective
reaction
allenes,
conjugated
enynes
1,3-dienes
is
achieved
a
designed
Pd/Co
dual
catalysis
newly
modified
masked
phosphinylating
reagent.
A
series
allyl
motifs
bearing
both
tertiary
C-
P-stereocenter
are
prepared
in
generally
good
yields,
>20
:
1
dr,
rr
99
%
ee.
The
unprecedented
1,3-enynes
established
to
generate
skeletons
containing
nonadjacent
chiral
axis.
first
stereodivergent
also
developed
achieve
all
four
P-containing
stereoisomers.
present
protocol
features
use
only
3-minutes
time
0.1
catalyst,
with
observation
up
730
TON.
set
mechanistic
studies
reveal
necessity
roles
two
metal
catalysts
corroborate
synergistic
process.
Green Chemistry,
Journal Year:
2024,
Volume and Issue:
26(7), P. 4199 - 4208
Published: Jan. 1, 2024
A
new
photoelectrocatalytic
mode
permits
the
synthesis
of
polycyclic
pyrimidin-4-ones
through
dehydrogenative
cyclization
malonates
with
unactivated
alkenes.
Angewandte Chemie International Edition,
Journal Year:
2023,
Volume and Issue:
62(34)
Published: June 30, 2023
Chain
walking
has
been
an
efficient
route
to
realize
the
functionalization
of
inert
C(sp3
)-H
bonds,
but
this
strategy
is
limited
mono-olefin
migration
and
functionalization.
Herein,
we
demonstrate
feasibility
tandem
directed
simultaneous
migrations
remote
olefins
stereoselective
allylation
for
first
time.
The
adoption
palladium
hydride
catalysis
secondary
amine
morpholine
as
solvent
critical
achieving
high
substrate
compatibility
stereochemical
control
with
method.
protocol
also
applicable
three
vicinal
bonds
thus
construct
continuous
stereocenters
along
a
propylidene
moiety
via
short
synthetic
process.
Preliminary
mechanistic
experiments
corroborated
design
dienes.
Organic & Biomolecular Chemistry,
Journal Year:
2023,
Volume and Issue:
22(1), P. 37 - 54
Published: Nov. 27, 2023
Developing
efficient
and
straightforward
strategies
to
rapidly
construct
structurally
distinct
diverse
organic
molecules
is
one
of
the
most
fundamental
tasks
in
synthesis,
drug
discovery
materials
science.
In
recent
years,
divergent
synthesis
functional
from
same
starting
has
attracted
significant
attention
been
recognized
as
an
powerful
strategy.
To
achieve
this
objective,
proper
adjustment
reaction
conditions,
such
catalysts,
solvents,
ligands,
etc.,
required.
review,
we
summarized
efforts
chemo-,
regio-
stereodivergent
reactions
involving
acyclic
cyclic
systems
catalyzed
by
palladium
complexes.
Meanwhile,
types,
including
carbonylative
reactions,
coupling
cycloaddition
well
probable
mechanism
have
also
highlighted
detail.
ACS Catalysis,
Journal Year:
2024,
Volume and Issue:
14(13), P. 9742 - 9751
Published: June 14, 2024
Due
to
the
instability
and
weak
O-nucleophilicity
of
enol,
carbonyl
compounds
prefer
function
as
C-nucleophiles
instead
O-nucleophiles
in
extensively
studied
transition
metal-catalyzed
hydrofunctionalizations
unsaturated
bonds.
The
corresponding
hydroalkenoxylation
reaction
has
thus
long
been
unexplored.
Here,
we
describe
a
chemodivergent
protocol
for
challenging
reactions.
Dictated
by
Pd
catalyst
bearing
different
ligands,
both
5-exo-trig
6-endo-trig
processes
are
demonstrated
be
feasible
between
1,3-enynes
ketoesters,
polysubstituted
hydrofurans
hydropyrans
achieved
good
yields
excellent
chemoselectivities.
In
addition,
enantioselective
is
also
explored
under
an
Rh
moderate
efficiency
but
with
high
stereoselectivities.
Mechanistic
studies
corroborate
designed
tandem
hydroalkylation
uncover
that
ligand-to-ligand
hydrogen
transfer
process
might
involved
turnover-limiting
step
hydroalkenoxylation.
Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(7), P. 1483 - 1488
Published: Feb. 12, 2024
Presented
herein
is
a
palladium-catalyzed
asymmetric
(3
+
2)
annulation
reaction
between
1,3-dienes
and
2-formylarylboronic
acids,
proceeding
in
cascade
vinylogous
addition
Suzuki
coupling
process.
Both
electron-neutral
electron-deficient
are
compatible
under
similar
catalytic
conditions,
distinct
regioselectivity
observed
via
functional-group
control
of
1,3-diene
substrates.
A
collection
1-indanols
with
dense
functionalities
constructed
stereoselectively.
Journal of the American Chemical Society,
Journal Year:
2023,
Volume and Issue:
145(39), P. 21638 - 21645
Published: Sept. 22, 2023
A
method
for
the
synthesis
of
allenes
by
addition
ketones
to
1,3-enynes
cooperative
Pd(0)Senphos/B(C6F5)3/NR3
catalysis
is
described.
wide
range
aryl-
and
aliphatic
undergo
various
in
high
yields
at
room
temperature.
Mechanistic
investigations
revealed
a
rate-determining
outer-sphere
proton
transfer
mechanism,
which
was
corroborated
DFT
calculations.
JACS Au,
Journal Year:
2024,
Volume and Issue:
4(5), P. 1744 - 1751
Published: May 10, 2024
Conjugated
dienes
(1,3-dienes)
are
versatile
and
valuable
chemical
feedstocks
that
can
be
used
as
two-carbon
or
four-carbon
synthons
with
vast
applications
across
the
industry.
However,
main
challenge
for
their
productive
incorporation
in
synthetic
routes
is
chemo-,
regio-,
stereoselective
functionalization.
Herein,
we
introduce
a
unified
strategy
1,2-hydroarylation
1,4-trifluoromethylarylation
of
1,3-dienes
using
anilines
hexafluoroisopropanol.
DFT
calculations
point
toward
kinetically
controlled
process
both
transformations,
particularly
trifluoromethylarylation,
to
explain
regiodivergent
outcome.
In
addition,
perform
an
extensive
program
functionalization
diversification
products
obtained,
including
hydrogenation,
oxidation,
cyclizations,
cross-coupling
reactions,
allows
access
library
high-value
species
straightforward
manner.
The Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
89(14), P. 9841 - 9852
Published: June 25, 2024
A
novel
methodology
for
the
synthesis
of
nitrones
via
palladium-catalyzed
redox
cross-coupling
nitro
compounds
and
alcohols
is
established.
The
protocol
a
mild,
convenient,
ligand-free,
scalable
method
that
can
be
compatible
with
various
alcohols.
Nitrone
significant
multifunctional
platform
synthon
which
synthesized
directly
efficiently
this
tactic
from
commercially
available
cheap
raw
materials.
