SynOpen,
Год журнала:
2018,
Номер
02(04), С. 0306 - 0311
Опубликована: Окт. 1, 2018
Herein,
we
present
the
first
Suzuki–Miyaura
cross-coupling
in
a
sustainable
natural
deep
eutectic
solvent
(NaDES)
applied
to
biologically
relevant
imidazo-fused
scaffolds
imidazo[1,2-a]pyridine
and
imidazo[1,2-b]pyridazine.
The
choline
chloride/glycerol
(1:2,
mol/mol)
NaDES
allowed
functionalisation
of
diverse
positions
on
heterocycles
with
various
boronic
acids,
by
using
2.5
mol%
readily
available
Pd(OAc)2.
Notably,
catalytic
system
proceeds
without
any
ligands
or
additives,
protection
from
atmosphere.
ACS Sustainable Chemistry & Engineering,
Год журнала:
2022,
Номер
10(9), С. 3037 - 3047
Опубликована: Фев. 22, 2022
An
optimized
protocol
for
the
Pd-catalyzed
direct
arylation
of
3,4-ethylenedioxythiophene
(EDOT)
and
other
substituted
thiophenes
with
(hetero)aromatic
bromides
in
a
deep
eutectic
solvent
made
mixture
choline
chloride/glycerol
(1:2)
is
presented.
The
coupling
reactions
have
been
successfully
run
under
air,
nonanhydrous
conditions,
using
PdCl2
as
palladium
source,
catalyst
loading
low
1
mol
%.
adjustment
each
reaction
component
allowed
finding
robust
conditions
introduction
both
electron-poor
electron-rich
(hetero)aryl
moderate-to-high
yields.
sustainability
was
established
through
calculations
green
metrics,
such
Eco-scale
E-factor,
compared
literature,
when
possible.
Remarkably,
procedure
can
be
applied
simple
preparation
conjugated
organic
compounds
potential
applications
optoelectronics,
we
shown,
by
obtaining
two
molecules
previously
reported
hole
transport
material
perovskite
solar
cells
final
intermediate
photosensitizer
dye-sensitized
cells.
The Journal of Organic Chemistry,
Год журнала:
2018,
Номер
83(16), С. 9312 - 9321
Опубликована: Июль 23, 2018
Direct
arylation
of
thienopyrrolodione,
diketopyrrolopyrroles,
benzodithiophene
derivatives,
and
fluorinated
heteroarenes
with
functionalized
aryl
iodides
is
proven
in
solvent-free
non-anhydrous
conditions.
The
reaction
performed
the
presence
air
tolerates
several
functional
groups
on
both
coupling
partners,
enabling
a
convenient
synthesis
extended
heteroaromatic
conjugated
molecules.
Organic Letters,
Год журнала:
2019,
Номер
21(17), С. 7044 - 7048
Опубликована: Авг. 27, 2019
Methods
to
catalytically
introduce
deuterium
in
synthetically
useful
yields
ortho
a
carboxylic
acid
directing
group
on
arenes
typically
requires
D2
or
high
catalyst
loadings,
which
makes
using
these
approaches
cost
prohibitive
for
large-scale
synthesis
(equipment
and
reagent
costs
respectively).
Herein,
we
present
simplified
approach
low
loadings
of
cationic
RhIII
D2O
as
both
source
solvent
show
its
application
H/D
exchange
various
substrates.
SynOpen,
Год журнала:
2018,
Номер
02(04), С. 0306 - 0311
Опубликована: Окт. 1, 2018
Herein,
we
present
the
first
Suzuki–Miyaura
cross-coupling
in
a
sustainable
natural
deep
eutectic
solvent
(NaDES)
applied
to
biologically
relevant
imidazo-fused
scaffolds
imidazo[1,2-a]pyridine
and
imidazo[1,2-b]pyridazine.
The
choline
chloride/glycerol
(1:2,
mol/mol)
NaDES
allowed
functionalisation
of
diverse
positions
on
heterocycles
with
various
boronic
acids,
by
using
2.5
mol%
readily
available
Pd(OAc)2.
Notably,
catalytic
system
proceeds
without
any
ligands
or
additives,
protection
from
atmosphere.
