Organic Process Research & Development,
Journal Year:
2019,
Volume and Issue:
23(8), P. 1529 - 1537
Published: June 17, 2019
The
palladium-catalyzed
coupling
of
aryl
and
heteroaryl
chlorides
with
primary
amides
under
mild
homogeneous
reaction
conditions
is
reported.
Successful
C–N
enabled
by
the
use
a
unique
"dual-base"
system
consisting
DBU
NaTFA,
which
serve
as
proton
acceptor
halide
scavenger,
respectively,
using
low
catalyst
loadings
(0.5
mol
%)
readily
available,
air-stable
palladium
precatalysts.
DBU/NaTFA
also
enables
room-temperature
amines
tolerant
variety
base-sensitive
functional
groups.
Organic Letters,
Journal Year:
2017,
Volume and Issue:
19(10), P. 2762 - 2765
Published: April 28, 2017
The
Zweifel
reaction
is
a
powerful
method
for
the
synthesis
of
alkenes,
serving
as
transition-metal-free
alternative
to
Suzuki–Miyaura
reaction.
To
date,
scope
coupling
has
been
rather
narrow
and
focused
mainly
on
vinyllithium
reagents
synthesize
simple
aryl-
alkyl-substituted
olefins.
Herein,
development
general
process
enabling
Grignard
or
organolithiums
described.
This
enables
enantiospecific
wide
variety
functionalized
acyclic
cyclic
olefin
products.
Angewandte Chemie International Edition,
Journal Year:
2017,
Volume and Issue:
56(39), P. 11870 - 11874
Published: July 25, 2017
Catalytic
enantioselective
conjunctive
cross-coupling
between
9-BBN
borate
complexes
and
aryl
electrophiles
can
be
accomplished
with
Ni
salts
in
the
presence
of
a
chiral
diamine
ligand.
The
reactions
furnish
derivatives
an
fashion
these
are
converted
to
alcohols
amines,
or
engaged
other
stereospecific
C-C
bond
forming
reactions.
Journal of the American Chemical Society,
Journal Year:
2018,
Volume and Issue:
140(45), P. 15181 - 15185
Published: Oct. 30, 2018
Enantio-
and
diastereoselective
conjunctive
cross-coupling
of
β-substituted
alkenylboron
"ate"
complexes
is
studied.
Whereas
β-substitution
shifts
the
chemoselectivity
catalytic
reaction
in
favor
Suzuki–Miyaura
product,
use
a
boronic
ester
ligand
derived
from
acenaphthoquinone
allows
process
to
even
with
substituted
substrates.
Journal of the American Chemical Society,
Journal Year:
2017,
Volume and Issue:
139(43), P. 15324 - 15327
Published: Oct. 13, 2017
Allylboronic
esters
react
readily
with
carbonyls
and
imines
(π-electrophiles),
but
are
unreactive
toward
a
range
of
other
electrophiles.
By
addition
an
aryllithium,
the
corresponding
allylboronate
complexes
display
enhanced
nucleophilicity,
enabling
to
electrophiles
(tropylium,
benzodithiolylium,
activated
pyridines,
Eschenmoser's
salt,
Togni's
reagent,
Selectfluor,
diisopropyl
azodicarboxylate
(DIAD),
MeSX)
in
high
regio-
stereocontrol.
This
protocol
provides
access
key
new
functionalities,
including
quaternary
stereogenic
centers
bearing
moieties
such
as
fluorine
trifluoromethyl
group.
The
were
determined
be
7
10
orders
magnitude
more
reactive
than
parent
boronic
ester.
Organic Process Research & Development,
Journal Year:
2019,
Volume and Issue:
23(8), P. 1529 - 1537
Published: June 17, 2019
The
palladium-catalyzed
coupling
of
aryl
and
heteroaryl
chlorides
with
primary
amides
under
mild
homogeneous
reaction
conditions
is
reported.
Successful
C–N
enabled
by
the
use
a
unique
"dual-base"
system
consisting
DBU
NaTFA,
which
serve
as
proton
acceptor
halide
scavenger,
respectively,
using
low
catalyst
loadings
(0.5
mol
%)
readily
available,
air-stable
palladium
precatalysts.
DBU/NaTFA
also
enables
room-temperature
amines
tolerant
variety
base-sensitive
functional
groups.
