Organic Letters,
Год журнала:
2024,
Номер
26(35), С. 7452 - 7456
Опубликована: Авг. 26, 2024
A
base-mediated
regioselective
[3
+
3]
annulation
of
alkylidene
malononitriles
with
trifluoromethyl
alkenes
was
described.
The
reaction
proceeds
through
sequential
intermolecular
SN2′
and
intramolecular
SNV-type
cyclization
by
cleaving
dual
C–F
bonds
in
a
group,
which
discriminate
multiple
carbon-nucleophilic
sites
using
single
base.
Various
bicycles
bearing
monofluorocyclohexene
motif
were
assembled
from
readily
available
starting
materials
under
mild
conditions
via
one-pot
cascade
approach.
Organic Chemistry Frontiers,
Год журнала:
2023,
Номер
11(3), С. 895 - 915
Опубликована: Дек. 20, 2023
Photoinduced
radical–polar
crossover
cyclization
(RPCC)
of
bifunctional
alkenes
is
high
synthetic
utility
to
produce
cyclic
products
with
precise
alkene
design.
This
review
summarizes
the
recent
representative
advances
in
field
RPC.
Organic Letters,
Год журнала:
2024,
Номер
26(12), С. 2511 - 2516
Опубликована: Март 20, 2024
This
work
demonstrates
the
synthesis
of
a
variety
perfluoroalkyl
heterocycles
via
visible-light-driven
radical-polar
crossover
cyclization
strategy.
In
this
process,
single-electron
reduction/SNV-type/cyclization
sequences
follow
radical
addition
reaction
diazoester,
which
differs
from
current
role
diazoesters
as
precursors/acceptors.
transformation
excellent
functional
group
compatibility
and
allows
for
modification
many
bioactive
molecules
with
diazoesters.
Such
could
represent
novel
approach
to
photochemical
diazo
compounds.
The Chemical Record,
Год журнала:
2024,
Номер
24(3)
Опубликована: Янв. 22, 2024
Abstract
The
increasing
demand
of
organofluorine
compounds
in
medicine,
agriculture,
and
materials
sciences
makes
sophisticated
methods
for
their
synthesis
ever
more
necessary.
Nowadays,
not
only
the
C−F
bond
formation
but
also
selective
cleavage
readily
available
poly‐
or
perfluorine‐containing
have
become
powerful
tools
effective
compounds.
defluorinative
cross‐coupling
trifluoromethyl
alkenes
with
various
nucleophiles
radical
precursors
an
S
N
2’
manner
is
a
convergent
route
to
access
gem
‐difluoroalkenes,
which
turn
react
via
V‐type
reaction.
If
V
reactions
occur
intramolecularly,
dual
allows
facile
assembly
monofluorinated
cyclic
skeletons
structural
complexity
diversity.
In
this
personal
account,
we
summarized
advances
field
on
basis
coupling
cyclization
partners,
including
binucleophiles,
alkynes,
diradical
bearing
nucleophilic
site.
Accordingly,
annulation
can
be
achieved
by
base‐mediated
sequential
2′/S
reactions,
transition
metal
catalyzed
mediated
photoredox
catalysis,
combination
photocatalytic
context
seminal
works
others
field,
concise
summary
contributions
authors
offered.
Organic Chemistry Frontiers,
Год журнала:
2024,
Номер
11(14), С. 3974 - 3981
Опубликована: Янв. 1, 2024
A
defluorinative
cyclization
of
readily
available
trifluoromethyl
enones
with
phosphine
oxides
for
the
synthesis
polysubstituted
furans
is
developed
in
a
pure
water
solution.
Green Chemistry,
Год журнала:
2023,
Номер
25(23), С. 9672 - 9679
Опубликована: Янв. 1, 2023
A
H
2
O-promoted
and
(NH
4
)
CO
3
-enabled
defluoroiminization
reaction
of
fluoroalkyl
alkenes
for
the
synthesis
fluoroalkylated
1,5-diazapentadienes
has
been
developed.
Organic Letters,
Год журнала:
2024,
Номер
26(28), С. 6030 - 6034
Опубликована: Июль 8, 2024
A
photoredox-catalyzed
sequential
decarboxylative/defluorinative
aminoalkylation
of
CF3-alkenes
with
N-arylglycines
is
described.
This
metal-free
and
redox-neutral
protocol
provided
efficient
access
to
the
monofluoroalkenyl-1,5-diamines
in
good
yields
excellent
functional
group
compatibility.
Mechanistic
studies
revealed
that
reaction
proceeds
via
a
radical
pathway
gem-difluoroalkenyl
amine
as
an
intermediate.
Organic Chemistry Frontiers,
Год журнала:
2024,
Номер
unknown
Опубликована: Ноя. 13, 2024
An
intermolecular
defluorinative
vicinal
diamination
protocol
employing
fluoroalkenyl
iodides
and
sulfonamides
for
the
efficient
synthesis
of
a
series
acyclic
cyclic
fluorinated
1,2-enediamines
has
been
developed.
Chinese Journal of Chemistry,
Год журнала:
2024,
Номер
42(12), С. 1360 - 1366
Опубликована: Фев. 23, 2024
Comprehensive
Summary
The
conversion
of
CF
3
‐alkenes
to
gem
‐difluoroalkenes
using
reductive
cross‐coupling
strategy
has
received
much
attention
in
recent
years,
however,
the
use
green
and
readily
available
reducing
salt
mediate
these
reactions
remains
be
explored.
In
this
work,
a
concise
construction
gem‐
difluoroalkenes,
which
requires
neither
catalyst
nor
metal
agent,
was
established.
Rongalite,
safe
inexpensive
industrial
product,
employed
as
both
radical
initiator
reductant.
This
procedure
compatible
with
linear
cyclic
diaryliodonium
salts,
enabling
wide
variety
substrates
(>70
examples).
utility
approach
demonstrated
through
gram‐scale
synthesis
efficient
late‐stage
functionalizations
anti‐inflammatory
drugs.
