Angewandte Chemie,
Journal Year:
2023,
Volume and Issue:
135(39)
Published: July 31, 2023
Abstract
Aryl
fluorides
are
important
structural
motifs
in
many
pharmaceuticals.
Although
the
Balz–Schiemann
reaction
provides
an
entry
to
aryl
from
aryldiazonium
tetrafluoroborates,
it
suffers
drawbacks
such
as
long
time,
high
temperature,
toxic
solvent,
gas
release,
and
low
functional
group
tolerance.
Here,
we
describe
a
general
method
for
synthesis
of
tetrafluoroborates
using
piezoelectric
material
redox
catalyst
under
ball
milling
conditions
presence
Selectfluor.
This
approach
effectively
addresses
aforementioned
limitations.
Furthermore,
can
be
recycled
multiple
times.
Mechanistic
investigations
indicate
that
this
fluorination
may
proceed
via
radical
pathway,
Selectfluor
plays
dual
role
both
source
fluorine
terminal
reductant.
Angewandte Chemie International Edition,
Journal Year:
2023,
Volume and Issue:
62(39)
Published: July 31, 2023
Abstract
Aryl
fluorides
are
important
structural
motifs
in
many
pharmaceuticals.
Although
the
Balz–Schiemann
reaction
provides
an
entry
to
aryl
from
aryldiazonium
tetrafluoroborates,
it
suffers
drawbacks
such
as
long
time,
high
temperature,
toxic
solvent,
gas
release,
and
low
functional
group
tolerance.
Here,
we
describe
a
general
method
for
synthesis
of
tetrafluoroborates
using
piezoelectric
material
redox
catalyst
under
ball
milling
conditions
presence
Selectfluor.
This
approach
effectively
addresses
aforementioned
limitations.
Furthermore,
can
be
recycled
multiple
times.
Mechanistic
investigations
indicate
that
this
fluorination
may
proceed
via
radical
pathway,
Selectfluor
plays
dual
role
both
source
fluorine
terminal
reductant.
The Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
89(8), P. 5371 - 5381
Published: March 29, 2024
A
facile
and
eco-friendly
photoinduced
dehydrogenative
amination
of
quinoxalin-2(1H)-ones
with
aliphatic
amines
without
any
metal,
strong
oxidant,
photocatalyst
has
been
established
for
the
first
time.
This
reaction
proceeding
efficiently
air
as
sole
oxidant
at
room
temperature
obtains
a
wide
range
3-aminoquinoxaline-2(1H)-ones
in
high
yields
excellent
functional
group
tolerance.
The
mechanistic
studies
show
an
interesting
involvement
photosensitizer,
which
eliminates
requirement
external
photocatalysts.
Angewandte Chemie International Edition,
Journal Year:
2024,
Volume and Issue:
63(28)
Published: April 30, 2024
Abstract
The
development
of
green
and
efficient
deuteration
methods
is
great
significance
for
various
fields
such
as
organic
synthesis,
analytical
chemistry,
medicinal
chemistry.
Herein,
we
have
developed
a
dehalogenative
strategy
using
piezoelectric
materials
catalysts
in
solid‐phase
system
under
ball‐milling
conditions.
This
non‐spontaneous
reaction
induced
by
mechanical
force.
D
2
O
can
serve
both
deuterium
source
an
electron
donor
the
transformation,
eliminating
need
additional
stoichiometric
exogenous
reductants.
A
series
(hetero)aryl
iodides
be
transformed
into
deuterated
products
with
high
incorporation.
method
not
only
effectively
overcomes
existing
synthetic
challenges
but
also
used
labelling
drug
molecules
derivatives.
Bioactivity
experiments
molecule
suggest
that
D‐ipriflavone
enhances
inhibitory
effects
on
osteoclast
differentiation
BMDMs
vitro
.
The Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
89(10), P. 7233 - 7242
Published: April 26, 2024
A
self-catalyzed,
visible-light-induced,
directly
selective
C3–H
aroylation
of
quinoxalin-2(1H)-ones
via
energy
transfer
and
hydrogen
atom
(HAT)
catalysis
has
been
developed.
The
method
is
highly
atom-economical,
eco-friendly,
easy
to
handle.
Notably,
the
reaction
proceeded
efficiently
with
ambient
air
as
sole
oxidant
at
room
temperature.
Chemistry - A European Journal,
Journal Year:
2024,
Volume and Issue:
30(47)
Published: June 18, 2024
Mechanochemical
reactions,
achieved
through
milling,
grinding,
or
other
mechanical
actions,
have
emerged
as
a
solvent-free
alternative
to
traditional
solution-based
chemistry.
Mechanochemistry
not
only
provides
the
opportunity
eliminate
bulk
solvent
use,
reducing
waste
generation,
but
also
unveils
new
reaction
strategy
which
enables
realization
of
reactions
previously
inaccessible
in
solution.
While
majority
organic
facilitated
by
force
traditionally
follow
two-electron
transfer
pathways
similar
their
counterparts,
field
mechanochemically
induced
single-electron
(SET)
has
witnessed
rapid
development.
This
review
outlines
examples
mechanochemical
SET
process,
focusing
on
reagents
that
initiate
SET,
thereby
positioning
mechanochemistry
burgeoning
within
realm
Angewandte Chemie International Edition,
Journal Year:
2024,
Volume and Issue:
63(49)
Published: Aug. 13, 2024
Abstract
The
1,2‐hydroxysilylation
of
alkenes
is
crucial
for
synthesizing
organosilicon
compounds
which
are
key
intermediates
in
material
science,
pharmaceuticals,
and
organic
synthesis.
development
strategies
employing
hydrogen
atom
transfer
pathways
currently
hindered
by
the
existence
various
competing
reactions.
Herein,
we
reported
a
novel
mechanochemical
strategy
triphasic
through
single‐electron‐transfer
pathway.
Our
approach
not
only
circumvents
competitive
reactions
to
enable
first‐ever
unactivated
but
also
pioneers
research
mechanic
force‐induced
under
ambient
conditions.
This
gentle
method
offers
excellent
compatibility
with
functional
groups,
operates
simple
solvent‐free
conditions,
ensures
rapid
reaction
time.
Preliminary
mechanistic
investigations
suggest
that
silylboronate
can
be
transformed
silicon
radical
highly
polarized
Li
2
TiO
3
particles
oxygen
ball‐milling
condition.
The Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
88(18), P. 12891 - 12901
Published: Aug. 24, 2023
An
air-tolerant
mechanoredox/nickel
cocatalyzed
cross
electrophile
coupling
of
benzotriazinones
with
alkyl
(pseudo)halides
is
developed
by
liquid-assisting
grinding
in
the
presence
manganese
powders
and
strontium
titanate
as
a
reductant
cocatalyst,
respectively.
Mechanical
activation
metal
surfaces
via
ball
milling
eliminates
chemical
activator
for
manganese,
while
mechanoredox
cocatalysis
remarkably
improves
aryl/alkyl
piezoelectricity-mediated
radical
generation
from
halides.
Both
display
reactivities
different
those
conventional
thermal
chemistry
solution.
The
scope
reaction
demonstrated
26
examples,
showing
high
chemoselectivity
bromides
vs
chlorides.
Materials Advances,
Journal Year:
2023,
Volume and Issue:
4(23), P. 6092 - 6117
Published: Jan. 1, 2023
This
review
provides
an
overview
of
different
piezoelectric
materials
and
the
latest
studies
regarding
piezoelectrically
mediated
organic
synthesis,
polymerization/crosslinking,
water
splitting,
remediation.
