Chemistry - A European Journal,
Journal Year:
2024,
Volume and Issue:
30(30)
Published: March 27, 2024
Abstract
Blue
LEDs‐irradiation
of
a
mixture
N,N,N',N'‐
tetramethylethylenediamine
(TMEDA)
and
perfluoroalkyl
iodides
(R
F
−I)
–
Electron
Donor
Acceptor
(EDA)‐complex
in
the
presence
triphenylamines
(TPAs)
an
aqueous
solvent
afforded
mono‐perfluoroalkylated
−TPA)
good
yields.
These
R
−TPA
were
further
subjected
to
acetone‐sensitized
[6π]‐electrocyclization
at
315
nm‐irradiation
affording
exclusively
perfluoroalkylated
endo‐carbazole
derivatives
−CBz)
quantitative
Mechanistic
studies
photophysical
properties
products
are
studied.
Molecules,
Journal Year:
2024,
Volume and Issue:
29(3), P. 569 - 569
Published: Jan. 23, 2024
Radical
reactions
in
water
or
aqueous
media
are
important
for
organic
synthesis,
realizing
high-yielding
processes
under
non-toxic
and
environmentally
friendly
conditions.
This
overview
includes
(i)
a
general
introduction
to
chemistry
media,
(ii)
synthetic
approaches
in,
on,
with
as
well
heterogeneous
phases,
(iii)
of
carbon-centered
radicals
(or
deuterium
oxide)
activated
through
coordination
various
Lewis
acids,
(iv)
photocatalysis
(v)
applications
bioinspired
by
naturally
occurring
processes.
A
wide
range
chemical
strategies
different
experimental
conditions
have
been
reviewed
that
lead
functional
group
translocation
transformation
reactions,
leading
the
preparation
complex
molecules.
These
results
reveal
how
solvent/medium/reagent
radical
has
matured
over
last
two
decades,
further
discoveries
anticipated
near
future.
Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(29), P. 6197 - 6202
Published: July 15, 2024
A
silver-promoted
three-component
heterocyclization
of
alkynes,
perfluoroalkyl
halides,
and
1,3-dinucleophiles
was
developed
for
the
efficient
synthesis
privileged
(E)-perfluoroalkenyl
pyrroles.
The
reaction
proceeded
through
a
rationally
designed
sequence
radical
perfluoroalkylation
intramolecular
defluorinative
[3
+
2]-heterocyclization.
utility
halide
as
perfluoroalkenyl
reagent,
by
selective
controllable
functionalization
two
inert
C(sp3)–F
bonds
at
vicinal
carbon
centers
on
chain,
provides
new
mode
value-added
organofluorides
starting
from
easily
available
low-cost
fluorinated
feedstock.
Organic Letters,
Journal Year:
2025,
Volume and Issue:
unknown
Published: Feb. 20, 2025
A
new
three-component
1,2-perfluoroalkyl
trifluoromethylthiolation
of
alkenes
via
dual
photoredox/copper
catalysis
has
been
established,
affording
a
variety
CnF2n+1/CF3S-containing
molecules
under
mild
conditions
in
redox-neutral
manner.
This
protocol
exhibits
excellent
functional
group
tolerance,
broad
compatibility
with
various
and
perfluoroalkyl
iodides,
potential
utility
the
modification
bioactive
molecules.
Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(11), P. 2271 - 2275
Published: March 8, 2024
A
clean
and
direct
three-component
radical
1,2-difunctionalization
of
various
alkenes
with
perfluoroalkyl
iodides
thiosulfonates
enabled
by
the
electron
donor–acceptor
complex
has
been
developed
under
light
illumination
at
room
temperature.
The
approach
offers
a
convenient
environmentally
friendly
route
for
simultaneous
incorporation
Csp3–Rf
Csp3–S
bonds,
affording
valuable
polyfunctionalized
alkane
derivatives
containing
fluorine
sulfur
in
satisfactory
yields.
Consequently,
this
methodology
holds
significant
value
practicality
field
organic
synthesis.
Advanced Science,
Journal Year:
2024,
Volume and Issue:
unknown
Published: Dec. 31, 2024
Abstract
Introducing
distinctive
functional
groups
to
expand
the
structural
diversity
and
improve
intrinsic
properties
of
parent
molecules
has
been
an
essential
pursuit
in
organic
chemistry.
By
using
perfluoroalkyl
halide
(PFAH)
as
a
nontraditional,
readily
available,
ideal
1,2‐difluoroalkenyl
coupling
partner,
defluorinative
cyclization
reaction
enamides
for
construction
fluoroalkenyl
oxazoles
is
first
developed.
The
selective
controllable
two‐fold
cleavage
vicinal
C(sp
3
)─F
bonds
PFAH
not
only
enables
introduction
specific
moiety
with
ease
but
also
results
functionalization
two
2
)─H
without
need
metal
catalyst,
photocatalyst,
oxidant,
or
light.
method
can
be
applied
late‐stage
modification
complex
molecules,
synthesis
biological‐relevant
oxazole
analoges,
scale‐up
synthesis,
which
all
further
highlight
real‐world
utility
this
protocol.
Mechanistic
studies
reveal
that
possibly
proceeds
through
radical
perfluoroalkylation,
consecutive
C─F
bond
heterolytic
cleavage,
process.
In
addition,
situ
formed
may
serve
hydrogen
abstractor.
Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(32), P. 6884 - 6888
Published: Aug. 1, 2024
The
electron
donor–acceptor
(EDA)
complexes
have
been
extensively
studied,
which
formed
an
electronically
excited
state,
obviating
the
need
for
exogenous
photocatalyst.
Herein,
we
report
a
mild
and
efficient
strategy
photoinduced
radical
domino
perfluoroalkylation/cyclization
using
N,N,N′,N′-tetramethylethane-1,2-diamine
(TMEDA)
as
donor.
This
protocol
could
be
well
expanded
to
access
various
polycyclic
quinazolinones
containing
perfluoroalkyl
groups,
exhibiting
photocatalyst-free,
good
functional
group
tolerance,
environmentally
friendly
features.
Organic Chemistry Frontiers,
Journal Year:
2024,
Volume and Issue:
unknown
Published: Nov. 13, 2024
An
intermolecular
defluorinative
vicinal
diamination
protocol
employing
fluoroalkenyl
iodides
and
sulfonamides
for
the
efficient
synthesis
of
a
series
acyclic
cyclic
fluorinated
1,2-enediamines
has
been
developed.
Organic Letters,
Journal Year:
2023,
Volume and Issue:
25(35), P. 6598 - 6602
Published: Aug. 29, 2023
A
method
for
hydrofluoroalkylation
of
alkenes
with
trifluoroacetic
esters
under
visible
light
irradiation
affording
difluorinated
products
is
described.
The
reaction
involves
readily
available
trimethyltriazinane
as
a
shoichiometric
reducing
agent,
which
generates
diamino-substituted
alkyl
radical
serving
strong
electron
donor.
It
believed
that
the
cleavage
C–F
bond
by
triazinane-derived
single
reduction
coupled
fluoride
transfer.
Chemical Communications,
Journal Year:
2024,
Volume and Issue:
60(18), P. 2532 - 2535
Published: Jan. 1, 2024
An
efficient
photocatalytic
method
was
developed
for
selective
perfluoroalkylation
of
terminal
alkynes
via
in-situ
generated
EDA
complexes
derived
from
a
thymol
anion
and
perfluoroalkyl
iodides.
