Organic Letters,
Journal Year:
2025,
Volume and Issue:
unknown
Published: Feb. 21, 2025
We
present
a
Pd-IPent-catalyzed
ring-opening
defluorinative
annulation
reaction
of
gem-difluorocyclopropanes
with
enamides,
which
provides
convenient
and
efficient
strategy
for
the
synthesis
multisubstituted
N-H
pyrrole
derivatives.
This
transformation
selectively
cleaves
C1-C3
bond,
two
C-F
bonds,
C-N
bond
in
one-pot
procedure.
Additionally,
this
protocol
allows
modification
several
bioactive
molecules.
Organic Letters,
Journal Year:
2022,
Volume and Issue:
24(45), P. 8429 - 8434
Published: Nov. 4, 2022
gem-Difluorinated
cyclopropanes
have
attracted
wide
research
interest
in
organic
synthesis
due
to
their
high
reactivity.
Herein,
we
report
a
Lewis
acid-catalyzed
cross-coupling
reaction
of
mono-
and
disubstituted
gem-difluorinated
with
nucleophiles.
The
formation
fluoroallyl
cation
species
triggered
via
the
acid-assisted
activation
C-F
bond
is
proposed
this
transformation.
then
trapped
by
nucleophiles,
including
electron-rich
arenes
allylsilanes,
deliver
series
fluoroallylic
products
good
yields.
provides
an
alternative
mode
for
using
as
surrogates.
Organic Letters,
Journal Year:
2022,
Volume and Issue:
24(33), P. 6176 - 6181
Published: Aug. 11, 2022
Herein,
we
report
an
effective
method
to
offer
chiral
gem-difluorinated
cyclopropanes
containing
all-carbon
quaternary
stereocenter
by
rhodium-catalyzed
stereoablative
kinetic
resolution.
The
activation
of
a
sterically
hindered
C–C
bond
through
oxidative
addition
with
rhodium
complex
is
proposed
as
the
enantiodetermining
step.
A
wide
range
can
be
obtained
excellent
ee
values
(ee
=
87%
>99.9%),
which
are
demonstrated
useful
fluorine-containing
building
blocks
series
postfunctionalizations.
Advanced Synthesis & Catalysis,
Journal Year:
2024,
Volume and Issue:
366(8), P. 1738 - 1743
Published: Feb. 17, 2024
Abstract
In
this
work,
we
reported
a
method
for
construction
of
difluorocyclopropanes
through
visible
light‐promoted
[1+2]
cycloaddition
reaction
aryl
diazo
esters
with
gem
‐difluoroalkenes.
The
proceeds
under
mild
conditions,
encompasses
wide
range
substrates
(36
examples),
exhibits
good
tolerance
to
various
substituents,
and
demonstrates
diastereoselectivity
>20:1.
Additionally,
antifungal
activity
evaluation
revealed
that
these
derivatives
exhibited
certain
activity,
the
EC
50
values
products
towards
Botrytis
cinerea
Rhizoctonia
solani
were
measured
be
1.51
1.36
μM,
respectively,
which
are
significantly
lower
than
those
commercial
fungicides
Hymexazol
Azoxystrobin.
This
work
not
only
provides
an
efficient
synthesis
difluorocyclopropanyl
derivatives,
but
reveals
their
potential
applications
in
fungicide
creation.
Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(32), P. 6905 - 6909
Published: Aug. 1, 2024
We
present
a
palladium-catalyzed
ring-opening
reaction
that
induces
indoles
to
cross-couple
with
gem-difluorocyclopropanes.
The
proceeds
through
domino
process
of
C–C
bond
activation
and
C–F
elimination,
followed
by
C–C(sp2)
coupling
produce
various
2-fluoroallylindoles.
This
method
is
characterized
its
high
functional
group
tolerance,
good
yields
regioselectivity,
under
base-free
conditions.
synthetic
utility
the
products
illustrated
functionalization
NH
C2
positions
indole
scaffold.
Organic Letters,
Journal Year:
2025,
Volume and Issue:
unknown
Published: Feb. 21, 2025
We
present
a
Pd-IPent-catalyzed
ring-opening
defluorinative
annulation
reaction
of
gem-difluorocyclopropanes
with
enamides,
which
provides
convenient
and
efficient
strategy
for
the
synthesis
multisubstituted
N-H
pyrrole
derivatives.
This
transformation
selectively
cleaves
C1-C3
bond,
two
C-F
bonds,
C-N
bond
in
one-pot
procedure.
Additionally,
this
protocol
allows
modification
several
bioactive
molecules.
