Organic Letters,
Journal Year:
2018,
Volume and Issue:
20(10), P. 3049 - 3052
Published: May 2, 2018
A
selective
oxy-alkylation
of
allylamines
with
unactivated
alkyl
bromides
and
CO2
via
visible-light-driven
palladium
catalysis
is
reported.
The
commercially
available
Pd(PPh3)4
used
as
the
sole
catalyst
in
this
three-component
reaction.
variety
tertiary,
secondary,
primary
undergo
reactions
to
generate
important
2-oxazolidinones
high
yields
selectivity.
mild
reaction
conditions,
easy
scalability,
facile
derivatization
products
provide
great
potential
for
application
organic
synthesis
pharmaceutical
chemistry.
Angewandte Chemie International Edition,
Journal Year:
2018,
Volume and Issue:
58(11), P. 3412 - 3416
Published: Dec. 6, 2018
Visible-light
induced,
palladium
catalyzed
alkylations
of
α,β-unsaturated
acids
with
unactivated
alkyl
bromides
are
described.
A
variety
primary,
secondary,
and
tertiary
activated
by
the
photoexcited
metal
catalyst
to
provide
a
series
olefins
at
room
temperature
under
mild
reaction
conditions.
Mechanistic
investigations
density
functional
theory
(DFT)
studies
suggest
that
photoinduced
inner-sphere
mechanism
is
operative
in
which
barrierless,
single-electron
transfer
oxidative
addition
halide
Pd0
key
for
efficient
transformation.
Chemistry - A European Journal,
Journal Year:
2018,
Volume and Issue:
24(18), P. 4552 - 4555
Published: Feb. 16, 2018
Abstract
The
palladium‐catalyzed
coupling
reaction
of
N
‐hydroxyphthalimide
esters
and
styrenes
to
deliver
exclusively
(
E
)‐substituted
olefins
under
irradiation
with
visible
light
is
reported.
This
method
tolerates
derived
from
primary,
secondary,
tertiary
as
well
benzylic
carboxylic
acids.
Notably,
Pd(PPh
3
)
4
employed
an
inexpensive
palladium
source
no
addition
base
or
classical
photocatalyst
required.
Mechanistic
studies
suggest
a
light‐mediated
single‐electron
reduction
the
activated
acid
by
photoexcited
palladium(0)
species
access
alkyl
radicals
through
decarboxylation.
Journal of the American Chemical Society,
Journal Year:
2019,
Volume and Issue:
141(46), P. 18405 - 18410
Published: Nov. 7, 2019
A
direct
and
versatile
copper-catalyzed
trifluoromethylthiolation
trifluoromethylselenation
of
primary,
secondary,
tertiary
aliphatic
C-H
bonds
was
developed.
The
reaction
provides
access
to
molecules
containing
these
emerging
moieties
in
the
presence
a
wide
range
common
functional
groups
complex
molecular
environments.
Angewandte Chemie International Edition,
Journal Year:
2018,
Volume and Issue:
58(6), P. 1794 - 1798
Published: Nov. 21, 2018
Abstract
The
Mizoroki–Heck
reaction
is
one
of
the
most
efficient
methods
for
alkenylation
aryl,
vinyl,
and
alkyl
halides.
Given
its
innate
nature,
this
protocol
requires
employment
compounds
possessing
a
halogen
atom
at
site
functionalization.
However,
accessibility
organic
molecules
particular
in
aliphatic
systems
extremely
limited.
Thus,
that
allows
Heck
to
occur
specific
nonfunctionalized
C(sp
3
)−H
desirable.
Reported
here
radical
relay
which
selective
remote
alcohols
unactivated
β‐,
γ‐,
δ‐C(sp
sites.
use
an
easily
installed/removed
Si‐based
auxiliary
enables
I‐atom/radical
translocation
events
C−H
sites
followed
by
reaction.
Notably,
proceeds
smoothly
under
mild
visible‐light‐mediated
conditions
room
temperature,
producing
highly
modifiable
valuable
alkenol
products
from
readily
available
feedstocks.
Organic Letters,
Journal Year:
2018,
Volume and Issue:
20(10), P. 3049 - 3052
Published: May 2, 2018
A
selective
oxy-alkylation
of
allylamines
with
unactivated
alkyl
bromides
and
CO2
via
visible-light-driven
palladium
catalysis
is
reported.
The
commercially
available
Pd(PPh3)4
used
as
the
sole
catalyst
in
this
three-component
reaction.
variety
tertiary,
secondary,
primary
undergo
reactions
to
generate
important
2-oxazolidinones
high
yields
selectivity.
mild
reaction
conditions,
easy
scalability,
facile
derivatization
products
provide
great
potential
for
application
organic
synthesis
pharmaceutical
chemistry.
