Journal of the American Chemical Society,
Journal Year:
2019,
Volume and Issue:
141(49), P. 19257 - 19262
Published: Nov. 11, 2019
Herein,
we
report
a
Ni-catalyzed
reductive
coupling
for
the
synthesis
of
benzonitriles
from
aryl
(pseudo)halides
and
an
electrophilic
cyanating
reagent,
2-methyl-2-phenyl
malononitrile
(MPMN).
MPMN
is
bench-stable,
carbon-bound
CN
reagent
that
does
not
release
cyanide
under
reaction
conditions.
A
variety
medicinally
relevant
can
be
made
in
good
yields.
Addition
NaBr
to
mixture
allows
use
more
challenging
electrophiles
such
as
chlorides,
tosylates,
triflates.
Mechanistic
investigations
suggest
plays
role
facilitating
oxidative
addition
with
these
substrates.
Angewandte Chemie International Edition,
Journal Year:
2020,
Volume and Issue:
60(6), P. 2849 - 2854
Published: Nov. 4, 2020
Abstract
A
metal‐
and
catalyst‐free
thiyl‐radical‐mediated
activation
of
alkanes
is
described.
Tetrafluoropyridinyl
disulfide
used
to
perform
thiolation
the
C−H
bonds
under
irradiation
with
400
nm
light‐emitting
diodes.
The
key
step
believed
proceed
via
hydrogen‐atom
abstraction
effected
by
fluorinated
thiyl
radical.
Secondary,
tertiary,
heteroatom‐substituted
can
be
involved
in
reaction.
resulting
sulfides
have
wide
potential
as
photoredox‐active
radical
precursors
reactions
alkenes
heteroarenes.
Organic Letters,
Journal Year:
2019,
Volume and Issue:
21(24), P. 9940 - 9944
Published: Nov. 21, 2019
A
general
protocol
for
the
hydroacylation
of
styrenes
from
aliphatic
carboxylic
acids
is
reported.
These
reactions
proceed
via
β-scission
a
phosphoranyl
radical
that
accessed
by
photoredox
catalysis,
followed
addition
resulting
acyl
to
styrenyl
olefin.
We
show
phosphine
tunability
critical
efficient
intermolecular
coupling
due
competitive
quenching
photocatalyst
Primary,
secondary,
and
structurally
rigid
tertiary
all
generate
valuable
unsymmetrical
dialkyl
ketones.
European Journal of Organic Chemistry,
Journal Year:
2020,
Volume and Issue:
2020(36), P. 5801 - 5814
Published: June 4, 2020
The
one‐electron
reduction
(OER)
can
profoundly
affect
the
structure
and
reactivity
of
organic
compounds.
OER
induced
radical
decarboxylative
functionalizations
redox‐active
esters
have
gained
wide
concerns
in
this
century.
In
review,
we
present
recent
advances
using
as
carbon‐centered
precursors
to
form
carbon–carbon
carbon–heteroatom
bonds.
