Organic Letters,
Journal Year:
2018,
Volume and Issue:
20(15), P. 4579 - 4583
Published: July 19, 2018
An
efficient
and
mild
zinc-mediated
decarboxylative
alkylation
of
gem-difluoroalkenes
with
N-hydroxyphthalimide
(NHP)
esters,
to
give
monofluoroalkenes
in
moderate
excellent
yields
high
Z-selectivity
is
reported.
The
reaction
tolerates
a
broad
range
functional
groups
can
be
easily
scaled
up,
which
thus
may
pave
the
way
for
its
further
applications
medicinal
chemistry
materials
science.
ACS Catalysis,
Journal Year:
2017,
Volume and Issue:
8(1), P. 242 - 257
Published: Nov. 20, 2017
Catalysis
by
defined
transition-metal
complexes
has
captivated
the
attention
of
scientific
community
over
last
decades.
The
well-documented
utility
Rh(III)
in
C–H
activation
reactions
have
enabled
development
a
plethora
new
catalytic
methods.
High-valent
species
were
first
predicted
palladium-based
transformations.
From
those
early
studies,
it
was
apparent
that
differences
reactivity
and
selectivity
could
be
expected.
By
analogy,
higher
valent
Rh(V)
represent
approach
offer
different
opportunities
to
improve
broaden
current
state-of-the-art
field.
ACS Catalysis,
Journal Year:
2019,
Volume and Issue:
9(10), P. 9127 - 9133
Published: Sept. 4, 2019
Enantioselective
Ni-catalyzed
reductive
aryl
monofluoroalkenylation
of
alkenes
between
bromides
and
gem-difluoroalkenes
has
been
developed.
The
reaction
proceeding
under
room
temperature
base-free
conditions
tolerates
a
wide
range
functional
groups
on
both
coupling
partners.
Various
synthetically
useful
oxindoles
containing
monofluoroalkenyl
substituent
are
obtained
in
good
yields
with
85%–95%
enantiomeric
excess.
In
addition,
the
synthetic
method
can
be
further
applied
to
late-stage
complex
biologically
active
compounds.
Synthesis,
Journal Year:
2018,
Volume and Issue:
50(05), P. 881 - 955
Published: Jan. 11, 2018
Monofluoroalkenes
have
found
wide
application
in
organic
chemistry,
medicinal
and
materials
science.
This
review
summarizes
the
most
recent
advances
made
regarding
preparation
of
monofluoroalkenes,
covering
period
between
October
2010
September
2017.
is
divided
three
main
parts,
one
for
each
possible
substitution
pattern,
namely
di-,
tri-,
tetrasubstituted.
Then,
class,
further
subclassification
according
to
reaction
type.
1
Introduction
2
Disubstituted
2.1
α-Monofluoroalkenes
2.2
β-Monofluoroalkenes
3
Trisubstituted
4
Tetrasubstituted
5
Conclusions
Chemical Communications,
Journal Year:
2020,
Volume and Issue:
56(72), P. 10442 - 10452
Published: Jan. 1, 2020
Three-component
difunctionalization
ofgem-difluoroalkenesviathe
generation
and
transformation
of
a
α-fluoroalkylated
carbanion,
carbon–metal
species,
radical,
carbocation
intermediate.
Israel Journal of Chemistry,
Journal Year:
2020,
Volume and Issue:
60(3-4), P. 313 - 339
Published: March 1, 2020
gem-Difluorinated
alkenes
are
readily
accessible
building
blocks
that
can
undergo
functionalization
to
provide
a
broad
spectrum
of
fluorinated
and
non-fluorinated
products.
Herein,
we
review
recent
(since
2017)
transition
metal-catalyzed
transformations
these
specialized
summarize
general
reactivity
patterns
reactions.
Many
reactions
net
C-F
bond
deliver
monofluorinated
These
typically
proceed
through
β-fluoro
alkylmetal
intermediates
eliminate
β-fluoride
monofluoroalkene
A
second
series
exploit
coinage
metal
fluorides
add
F-
the
gem-difluorinated
alkene,
further
delivers
trifluoromethyl-containing
In
stark
contrast,
few
in
"fluorine-retentive
processes"
difluoromethylene-based
Advanced Synthesis & Catalysis,
Journal Year:
2017,
Volume and Issue:
360(5), P. 1032 - 1037
Published: Dec. 27, 2017
Abstract
The
copper‐catalyzed
stereoselective
defluorinative
borylation
and
silylation
of
gem
‐difluoroalkenes
was
developed.
protocol
led
to
the
exclusive
formation
Z
type
monofluoroalkenyl
borons
silanes
in
generally
good
efficiency
with
broad
substrate
scope.
products
formed
could
be
readily
transformed
other
F‐containing
molecules
by
taking
advantage
versatile
reactivities
C−B
C−Si
bonds.
Experimental
theoretical
mechanistic
studies
were
conducted
which
support
an
olefin
insertion/
syn
‐planar
β‐F
elimination
pathway.
magnified
image
Chemistry - A European Journal,
Journal Year:
2017,
Volume and Issue:
23(50), P. 12145 - 12148
Published: July 4, 2017
Sustainable,
cobalt-catalyst
enabled,
synthetically
significant
C-F/C-H
functionalizations
were
achieved
with
an
ample
substrate
scope
at
ambient
temperature
of
25
°C,
thereby
delivering
perfluoroallylated
heteroarenes.
Detailed
experimental
and
computational
mechanistic
studies
on
the
provided
strong
support
for
a
facile
C-F
cleavage.
