Organic Letters,
Journal Year:
2022,
Volume and Issue:
24(17), P. 3194 - 3198
Published: April 25, 2022
The
development
of
mild
and
practical
conditions
for
the
fluoroalkylation
arenes
is
an
ongoing
challenge
in
chemical
organic
synthesis.
Herein,
we
report
a
metallaphotoredox
method
preparation
fluoroalkyl
based
on
synergistic
combination
Ir/Cu
dual
catalysis
from
boronic
acids.
allow
broad
functional
group
tolerance,
including
substrates
containing
aldehydes,
free
phenols,
N-Boc-protected
amines.
Mechanistic
investigations
support
process
proceeding
via
photoredox/copper
catalysis.
Advanced Synthesis & Catalysis,
Journal Year:
2021,
Volume and Issue:
363(12), P. 2912 - 2968
Published: Feb. 5, 2021
Abstract
For
almost
40
years,
difluoromethylene
phosphonates
have
proven
to
be
versatile
molecular
tools
in
biochemical
studies
owing
their
close
resemblance
naturally
occurring
phosphates
and
phosphonates.
As
bioisosteric,
non‐hydrolyzable
analogs
of
these
essential
molecules,
can
target
the
critical
parts
cellular
machinery
therefore
exhibit
a
diverse
spectrum
biological
activity.
In
past
ten
there
appeared
many
new
methods
for
synthesis
Most
notably,
photoredox
catalysis
has
firmly
entered
field,
while
cross‐coupling
nucleophilic
strategies
met
considerable
elaboration
refinement,
entirely
accord
with
current
trends
synthetic
organic
chemistry.
Herein,
we
introduce
as
distinct,
high‐tech
subclass
resulting
from
research
efforts
on
cross‐section
organophosphorus,
organofluorine,
bioorganic
We
then
proceed
discussion
general
preparation
phosphonates,
comprehensively
reviewing
reactions
developed
15
years
providing
context
earlier
works
where
appropriate.
Finally,
present
selected
examples
molecules
high
activity,
targets,
steps
employed
preparation.
magnified
image
Synthesis,
Journal Year:
2022,
Volume and Issue:
54(08), P. 1919 - 1938
Published: Feb. 21, 2022
Abstract
Perfluoroalkylation
is
one
of
the
most
important
methods
for
introduction
multiple
fluorine
atoms
into
organic
molecules
in
a
single
step.
The
use
photoinduced
technology
common
strategy
that
uses
outstanding
oxidation
or
reduction
ability
photoredox
catalyst
its
excited
state
to
generate
perfluoroalkyl
radicals
from
halides.
thus
obtained
can
undergo
various
subsequent
reactions
under
mild
conditions,
such
as
ATRA
reaction
alkenes,
alkynes,
and
1,n-enynes;
carbo/heteroperfluoroalkylation
alkenes
isocyanides;
C–H/F
perfluoroalkylation.
This
allows
expedient
incorporation
groups
molecular
motifs.
Perfluorinated
functional
are
still
demand
pharmaceutical
material
sciences;
this
short
review
discusses
recent
advances
perfluoroalkylation
methodologies
technologies.
1
Introduction
2
Photocatalytic
Alkenes,
Alkynes,
1,n-
Enynes
3
Carboperfluoroalkylation
Heteroperfluoroalkylation
Isocyanides,
Hydrazones
4
ATRE
Reactions
Alkenes
with
Perfluoroalkyl
Halides
5
C–X
(X
=
H,
F)
Bond
6
Continuous
Flow
Strategies
7
Conclusions
Chemistry - A European Journal,
Journal Year:
2022,
Volume and Issue:
28(41)
Published: May 11, 2022
Abstract
Perfluoroalkylated
(hetero)arenes
represent
an
extremely
important
family
of
molecules
commonly
utilized
in
many
areas
such
as
medicinal
chemistry,
agrochemistry
and
material
sciences.
Due
to
their
unique
properties,
they
have
attracted
significant
interest
from
synthetic
chemists
various
methods
been
developed
for
synthesis.
Among
them,
the
direct
perfluoroalkylation
C(sp
2
)−H
bonds
is
one
most
attractive
straightforward
ones,
provided
that
it
proceeds
with
high
levels
regioselectivity.
In
this
review
article,
a
comprehensive
overview
advances
field
presented,
special
focus
on
reaction
mechanisms
involved
these
transformations
All
available
classified
according
nature
perfluoroalkyl
chain
introduced,
trifluoromethylation
reactions
being
overviewed
separate
section,
reagents/catalysts
required.
Angewandte Chemie International Edition,
Journal Year:
2022,
Volume and Issue:
61(30)
Published: May 20, 2022
Abstract
A
novel
distal
radical
rearrangement
of
alkoxyphosphine
is
developed
for
the
first
time
and
applied
to
regioselective
fluoroalkylphosphorylation
unactivated
olefins.
By
employing
a
one‐pot
two‐step
reaction
(bis)homoallylic
alcohols,
organophosphine
chlorides,
fluoroalkyl
iodides
under
CFL
(compact
fluorescence
light)
irradiation,
series
fluoroalkylphosphorylated
alkyl
alcohols
are
easily
synthesized
by
regiospecific
installing
phosphonyl
onto
inner
carbon
terminal
olefins
further
iodination/hydroxylation.
Mechanism
studies
reveal
that
migration
undergoes
distinctive
cyclization/β‐scission
on
lone
electron
pair
phosphorus,
resulting
in
C−P
bond
formation
C−O
cleavage.
Advanced Synthesis & Catalysis,
Journal Year:
2020,
Volume and Issue:
363(4), P. 924 - 936
Published: Dec. 24, 2020
Abstract
The
photochemistry
of
organophosphorus
compounds
and
their
reactions
with
carbon‐centred
radicals
was
studied
from
the
1950s
to
70s,
but
has
not
been
well
exploited
in
synthetic
chemistry
until
very
recently.
This
review
discusses
various
modes
reactivity
that
phosphorus
display
radical
C−C
bond
forming
reactions,
including
role
phosphonium
salts
as
precursors,
phosphines
phosphites
deoxygenating
agents
oxygen‐centred
electron‐
charge‐transfer
chemistry.
We
also
highlight
potential
these
processes
have
future
development
new
cascade
processes.
magnified
image
Organic Letters,
Journal Year:
2021,
Volume and Issue:
24(1), P. 446 - 450
Published: Dec. 16, 2021
Exploiting
charge-transfer
complexes
in
visible
light-promoted
single-electron
redox
reactions
is
a
promising
route
for
opening
novel
synthetic
pathways,
and
catalytic
approaches
to
complex
formation
are
critical
facilitating
this
chemistry.
This
report
describes
the
use
of
substituted
hydroquinone
catalyst
promote
radical
perfluoroalkylation
reactions.
Mechanistic
studies
indicate
that
reaction
initiated
through
light-absorbing
halogen
bonding
between
perfluoroalkyl
halide
precursor.
Green Chemistry,
Journal Year:
2023,
Volume and Issue:
25(9), P. 3453 - 3461
Published: Jan. 1, 2023
Halogen
bonding-assisted
C
sp
3
–Br
homolysis
and
bromine
radical-mediated
oxidative
deboronation
make
visible-light-driven
photocatalyst-free
alkyl
Suzuki–Miyaura
coupling
of
alkenylboronic
acids/esters
with
α-bromodifluoroacylarenes
accessible.
Bulletin of the Korean Chemical Society,
Journal Year:
2024,
Volume and Issue:
45(9), P. 738 - 758
Published: Sept. 1, 2024
Abstract
Halogenation
is
one
of
the
most
important
transformations
in
organic
synthesis.
Halogenated
compounds
are
employed
many
reactions
to
prepare
useful
molecules.
Many
methods
have
been
developed
introduce
halogens
into
different
compounds.
Visible
light‐mediated
efficient,
low‐toxic,
and
mild‐condition
applied
for
various
chemistry
transformations.
Remarkably,
there
has
an
increasing
development
application
visible
light‐induced
halogenation
recent
years.
Herein,
we
present
a
comprehensive
summary
including
chlorination,
bromination,
iodination
under
light
irradiation
since
2020.
Advanced Synthesis & Catalysis,
Journal Year:
2022,
Volume and Issue:
364(13), P. 2248 - 2253
Published: May 13, 2022
Abstract
Arylation
of
tertiary
aryl
and
alkyl
phosphines
bearing
2‐cyanoethyl
group
with
aryl(mesityl)iodonium
triflates
under
blue
light
irradiation
followed
by
retro‐Michael
reaction
the
in
situ
generated
quaternary
phosphonium
salts
initiated
DBU
represent
a
novel
efficient
general
method
for
preparation
distinctly
substituted
arylphosphines.
An
operationally
simple,
one‐pot
protocol
features
mild,
transition‐metal‐free
conditions,
high
selectivity,
broad
functional
compatibility,
as
well
scalability
would
be
applied
to
substrates
different
electronic
steric
nature.
magnified
image
