European Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
unknown
Published: Sept. 6, 2023
Abstract
Herein,
we
report
an
efficient
protocol
in
which
formate
is
used
as
a
precursor
of
the
CO
2
radical
anion
for
photoinduced
defluorocarboxylation
α‐trifluoromethylstyrene.
A
wide
range
gem
‐difluorovinylacetic
acids
bearing
variety
functional
groups
were
successfully
obtained
absence
metal
catalysts.
The
synthetic
value
this
was
highlighted
by
successful
gram‐scale
synthesis
and
late‐stage
modification
complex
biologically
active
molecules.
This
provides
complementary
method
that
extends
currently
available
methodologies
accessing
structurally
versatile
‐difluoroalkenes.
Organic Letters,
Journal Year:
2023,
Volume and Issue:
25(10), P. 1748 - 1753
Published: March 3, 2023
Herein,
a
nickel-catalyzed
defluorinative
three-component
coupling
of
trifluoromethyl
alkenes,
internal
alkynes,
and
organoboronic
acids
is
presented.
The
protocol
provides
highly
efficient
selective
route
for
the
synthesis
structurally
diverse
gem-difluorinated
1,4-dienes
under
mild
conditions.
Mechanistic
studies
suggest
that
C-F
bond
activation
proceeds
probably
through
oxidative
cyclization
alkenes
with
Ni(0)
species,
sequential
addition
to
β-fluorine
elimination.
Organic Letters,
Journal Year:
2023,
Volume and Issue:
25(22), P. 4168 - 4172
Published: May 26, 2023
Described
here
is
a
simple
and
efficient
method
to
prepare
organoboron
compounds
through
α-deprotonation
functionalization
of
benzylboronates.
In
addition
alkyl
halides,
chlorosilane,
deuterium
oxide,
trifluoromethyl
alkene
could
also
serve
as
electrophiles
in
this
approach.
Notably,
the
boryl
group
enables
high
diastereoselectivities
when
unsymmetrical
secondary
α-bromoesters
are
used.
This
methodology
exhibits
broad
substrate
scope
atomic
efficiency
offers
an
alternative
C-C
bond
disconnection
for
synthesis
The Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
89(20), P. 15234 - 15247
Published: Oct. 8, 2024
A
transition-metal-free
late-stage
decarboxylative
gem-difluoroallylation
of
carboxylic
acids
with
α-trifluoromethyl
alkenes
has
been
described
by
the
use
organo-photoredox
catalysis.
Both
primary
alkyl
and
heteroaryl
were
readily
incorporated.
This
approach
merits
feedstock
materials,
mild
reaction
conditions,
wide
functionality
tolerance.
The
synthetic
utility
this
highlighted
functionalization
a
variety
acid-containing
natural
products
drug
molecules.
European Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
unknown
Published: Sept. 6, 2023
Abstract
Herein,
we
report
an
efficient
protocol
in
which
formate
is
used
as
a
precursor
of
the
CO
2
radical
anion
for
photoinduced
defluorocarboxylation
α‐trifluoromethylstyrene.
A
wide
range
gem
‐difluorovinylacetic
acids
bearing
variety
functional
groups
were
successfully
obtained
absence
metal
catalysts.
The
synthetic
value
this
was
highlighted
by
successful
gram‐scale
synthesis
and
late‐stage
modification
complex
biologically
active
molecules.
This
provides
complementary
method
that
extends
currently
available
methodologies
accessing
structurally
versatile
‐difluoroalkenes.
