The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(11), С. 7790 - 7794
Опубликована: Май 29, 2024
The
incorporation
of
difluoromethylene
groups
into
aza-heterocycles
represents
a
compelling
yet
underexplored
avenue
in
contemporary
chemical
research.
In
this
study,
we
unveil
hybrid
palladium-catalyzed
intramolecular
gem-difluoroalkylamination
conjugated
dienes,
providing
versatile
approach
to
the
synthesis
diverse
functionalized
pyrrolidines.
Noteworthy
features
include
mild
reaction
conditions
and
remarkable
tolerance
toward
various
functional
groups.
Additionally,
use
alkyl
iodides
as
electrophiles
facilitates
generation
corresponding
alkylamination
products.
Control
experiments
support
proposed
radical–polar
crossover
pathway,
offering
insights
underlying
processes
governing
transformation.
Organic Letters,
Год журнала:
2023,
Номер
25(20), С. 3745 - 3749
Опубликована: Май 11, 2023
The
auxiliary
function
of
a
carbonyl
group
in
the
tunable
defluorophosphination
and
defluorophosphorylation
trifluoromethylated
enones
with
P(O)-containing
compounds
was
demonstrated.
Controlled
replacement
one
or
two
fluorine
atoms
while
maintaining
high
chemo-
stereoselectivity
achieved
under
mild
conditions,
thus
enabling
diversity-oriented
synthesis
skeletally
diverse
organophosphorus
libraries─(Z)-difluoro-1,3-dien-1-yl
phosphinates,
(1Z,3E)-4-phosphoryl-4-fluoro-buta-1,3-dien-1-yl
(E)-4-phosphoryl-4-fluoro-1,3-but-3-en-1-ones─in
good
yields
excellent
functional
tolerance.
A
robust
and
practical
difluoroalkylation
synthon,
α,α-difluoroenol
species,
which
generated
in
situ
from
trifluoromethyl
diazo
compounds
water
the
presence
of
dirhodium
complex,
is
disclosed.
As
compared
to
presynthesized
difluoroenoxysilane
formed
difluoroenolate
under
basic
conditions,
this
difluoroenol
intermediate
displayed
versatile
reactivity,
resulting
dramatically
improved
enantioselectivity
mild
conditions.
demonstrated
catalytic
asymmetric
aldol
reaction
Mannich
reactions
with
ketones
or
imines
chiral
organocatalysts,
quinine-derived
urea,
phosphoric
acid
(CPA),
respectively,
relay
catalysis
strategy
provides
an
effective
platform
for
applying
fluorination
chemistry.
Moreover,
method
features
a
novel
1,2-difunctionalization
process
via
installation
carbonyl
motif
alkyl
group
on
two
vicinal
carbons,
complementary
protocol
metal
carbene
gem-difunctionalization
reaction.
Green Chemistry,
Год журнала:
2023,
Номер
25(22), С. 9292 - 9300
Опубликована: Янв. 1, 2023
A
novel
ATRA
reaction
was
developed
from
simple
and
widely
accessible
alkenes,
thiols,
trifluoromethylarenes
vis
photo-induced
EDA
complex
strategy.
Several
complicated
bioactive
molecules
undergo
smoothly
the
one-pot
photosynthetic
process.
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(11), С. 7790 - 7794
Опубликована: Май 29, 2024
The
incorporation
of
difluoromethylene
groups
into
aza-heterocycles
represents
a
compelling
yet
underexplored
avenue
in
contemporary
chemical
research.
In
this
study,
we
unveil
hybrid
palladium-catalyzed
intramolecular
gem-difluoroalkylamination
conjugated
dienes,
providing
versatile
approach
to
the
synthesis
diverse
functionalized
pyrrolidines.
Noteworthy
features
include
mild
reaction
conditions
and
remarkable
tolerance
toward
various
functional
groups.
Additionally,
use
alkyl
iodides
as
electrophiles
facilitates
generation
corresponding
alkylamination
products.
Control
experiments
support
proposed
radical–polar
crossover
pathway,
offering
insights
underlying
processes
governing
transformation.
