Mini-Reviews in Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
21(4), P. 455 - 470
Published: May 12, 2023
Abstract:
Since
its
discovery
at
the
beginning
of
20th
century,
trifluoroacetic
acid,
commonly
known
as
TFA,
has
seen
extensive
application
in
organic
synthesis
both
a
solvent
and
catalyst/
reagent.
TFA
can
be
used
to
facilitate
wide
variety
chemical
transformations,
including
rearrangements,
functional
group
deprotections,
condensations,
hydroarylations
trifluoroalkylations,
among
others.
The
decennial
mini-review
examines
key
synthetic
applications
from
middle
2013
present,
providing
chemistry
research
community
with
an
opportunity
delve
deeply
into
numerous
varied
this
strong
water-miscible,
low
boiling
point
Chemical Communications,
Journal Year:
2025,
Volume and Issue:
unknown
Published: Jan. 1, 2025
This
study
demonstrates
a
visible-light-driven
intramolecular
alkene
difluorination
enabling
Heck-type
coupling,
hydrofluoramidation,
and
difunctionalization.
Diverse
difluoro-γ-lactams
were
synthesized
with
high
selectivity
substrate
generality.
Chemistry - An Asian Journal,
Journal Year:
2025,
Volume and Issue:
unknown
Published: March 12, 2025
Abstract
A
copper‐catalyzed
remote
1,5‐trifluoromethyl
thio(seleno)cyanation
of
5‐hexenenitriles
with
an
intramolecular
cyano
migration
has
been
established,
affording
a
variety
CF
3
/CN‐containing
thiocyanates
and
selenocyanates
under
mild
conditions.
The
reaction
features
high
chemo‐
regioselectivities
illustrates
potential
value
in
synthetic
chemistry.
ACS Sustainable Chemistry & Engineering,
Journal Year:
2023,
Volume and Issue:
11(50), P. 17816 - 17825
Published: Dec. 4, 2023
A
novel
mechanochemical
method
was
proposed
to
achieve
a
radical-mediated
carbotrifluoromethylation
of
unactivated
alkenes
by
merging
piezoelectric
materials
BaTiO3
and
ball
milling,
which
has
significant
advantages,
such
as
ease
handling,
recyclable
catalysts,
air
compatibility,
less
solvent
consumption.
In
addition
its
wide
substrate
applicability,
this
also
been
proven
be
robust
green
approach
through
an
up-scaled
experiment,
catalyst
recycling
chemistry
metrics
analysis.
The
efficient
sustainable
mechanoredox
strategy
is
first
used
for
multiple
cascade
radical
reaction
provides
rapid
access
the
difunctionalized
fluorine-containing
ketone
scaffolds.
Angewandte Chemie International Edition,
Journal Year:
2024,
Volume and Issue:
63(41)
Published: July 18, 2024
Abstract
Although
highly
appealing
for
rapid
access
of
molecular
complexity,
multi‐functionalization
alkenes
that
allows
incorporation
more
than
two
functional
groups
remains
a
prominent
challenge.
Herein,
we
report
novel
strategy
merges
dipolar
cycloaddition
with
photoredox
promoted
radical
ring‐opening
remote
C(sp
3
)−H
functionalization,
thus
enabling
smooth
1,2,5‐trifunctionalization
unactivated
alkenes.
A
regioselective
[3+2]
anchors
reaction
trigger
onto
alkene
substrates.
The
subsequent
halogen
atom
transfer
(XAT)
selectively
initiates
process,
which
is
followed
by
series
1,5‐hydrogen
(1,5‐HAT)
and
intermolecular
fluorine
(FAT)
events.
With
this
method,
site‐selective
introduction
three
different
accomplished
broad
spectrum
valuable
β‐hydroxyl‐ϵ‐fluoro‐nitrile
products
are
synthesized
from
readily
available
terminal
The Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
89(16), P. 11682 - 11692
Published: Aug. 1, 2024
Alkene
difunctionalization
is
a
very
attractive
tool
in
synthetic
organic
chemistry.
Herein,
we
disclose
an
operationally
and
practically
simple
method
to
access
2-hydroxytrifluoroethylacetophenones
from
styrene
derivatives
via
photoredox
catalysis.
This
light-mediated
transformation
promotes
the
generation
of
1-hydroxy-2,2,2-trifluoroethyl
carbon-centered
radical
as
key
synthon,
which
undergoes
Giese
addition
with
styrenes
followed
by
Kornblum
oxidation
process.
The
presented
not
only
mild
cost-effective,
but
also
utilizes
photocatalyst
DMSO
oxidant.
Experimental
investigations
support
operative
mechanism
net-neutral
radical/polar
crossover.
European Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
26(29)
Published: June 14, 2023
Abstract
Difluoroalkyl
groups
and
cyclopentenones
are
both
important
units
in
synthetic
medicinal
chemistry.
The
difuoroalkylation
coupled
with
a
cyclopentenone
formation
still
remains
challenge.
Herein,
we
report
visible‐light‐induced
cascade
difluoroalkylative
5‐
endo
cyclization
of
ynones
difluoroalkyl
bromides
to
access
difluoroalkylated
cyclopentenones,
which
may
find
wide
applications
for
the
concise
synthesis
fluorinated
cyclic
molecules.
Organic Letters,
Journal Year:
2023,
Volume and Issue:
25(45), P. 8168 - 8172
Published: Nov. 3, 2023
Despite
the
importance
of
monofluoroalkyl
groups
in
pharmaceutically
relevant
molecules,
catalytic
protocols
for
their
incorporation
into
alkenes
remain
limited.
We
describe
herein
a
three-component
acylmonofluoroalkylation
introduction
such
moieties
through
an
unprecedented
cooperativity
between
N-heterocyclic
carbene
catalyst
and
earth-abundant
Mn(II)
complex.
This
general
method
can
be
applied
to
variety
alkenes,
including
styrenes,
1,3-enynes,
allenes,
as
well
complex
substrates
containing
natural
product
drug
motifs.
