New Opportunities to Access Fluorinated Molecules Using Organophotoredox Catalysis via C(sp3)–F Bond Cleavage
JACS Au,
Год журнала:
2025,
Номер
5(2), С. 466 - 485
Опубликована: Фев. 7, 2025
Fluorinated
molecules
are
of
paramount
importance
because
their
unique
properties.
As
a
result,
the
search
for
innovative
approaches
to
synthesis
this
class
compounds
has
been
relentless
over
years.
Among
these,
combination
photocatalysis
and
organofluorine
chemistry
turned
out
be
an
effective
partnership
access
unattainable
fluorinated
molecules.
This
Perspective
provides
overview
recent
advances
in
synthesizing
via
organophotoredox-catalyzed
defluorination
process
from
trifluoromethylated
compounds.
It
encompasses
preparation
difluoromethylated
(hetero)arenes,
amides,
esters
as
well
gem-difluoroalkene
derivatives
using
C(sp3)–F
bond
activation
or
β-fragmentation.
will
highlight
remaining
challenges
discuss
future
research
opportunities.
Язык: Английский
Photoredox/Copper Cooperatively Catalyzed Arylalkynylation of [1.1.1]Propellane
Organic Letters,
Год журнала:
2025,
Номер
unknown
Опубликована: Март 20, 2025
We
present
a
sp2–sp3/sp3–sp
bond
formation
reaction
through
three-component
coupling
strategy
involving
terminal
alkynes,
[1.1.1]propellane,
and
aryl
thianthrenium
salts
that
are
prepared
from
arenes.
The
employs
dual
photo/copper
catalysis
system
provides
streamlined
approach
for
assembling
1-alkynyl-3-aryl
bicyclo[1.1.1]pentane
derivatives
with
broad
spectrum
of
functional
group
compatibility.
Mechanistic
studies
suggest
the
generation
radicals
copper
alkynide
intermediates
was
involved.
Язык: Английский
Copper-Catalyzed Diastereoselective Addition of a [1,1,1]Propellane Dimer to N-tert-Butanesulfinyl Aldimines
Organic Letters,
Год журнала:
2025,
Номер
unknown
Опубликована: Март 21, 2025
[1,1,1]Propellane
is
typically
used
as
a
building
block
for
the
construction
of
bicyclo[1,1,1]pentanes
and
cyclobutanes.
In
this
work,
diverse
chiral
bi(methylenecyclobutylidene)
complexes
were
synthesized
by
diastereoselective
addition
[1,1,1]propellane
dimer
to
N-tert-butanesulfinyl
aldimines
in
presence
copper
bipyridine.
Density
functional
theory
calculations
revealed
that
both
step
regeneration
catalyst
contributed
generation
favored
(Ss,S,S)-diastereomer.
Язык: Английский
Photocatalytic Difunctionalization of [1.1.1]Propellane
The Chemical Record,
Год журнала:
2025,
Номер
unknown
Опубликована: Март 27, 2025
The
hunt
for
new
molecular
structures
to
improve
the
efficacy
of
biologically
active
molecules
is
at
forefront
pharmaceutical
chemistry.
So
synthetic
chemists
have
always
been
busy
in
last
few
decades
synthesizing
and
testing
frameworks
which
would
work
as
more
efficient
bioisosteres
present
bioactive
functional
groups.
In
this
area,
bicyclo[1.1.1]pentane
(BCP)
framework
has
identified
a
promising
candidate.
It
being
utilized
bioisostere
aryl,
tert-butyl,
alkynes,
etc.
Now
major
precursor
various
BCP
derivatives
[1.1.1]propellane
functionalization
drawn
widespread
attention
organic
chemist
community.
Over
past
two
decades,
use
visible
light
synthesis
rapidly
gained
popularity,
it
represents
one
most
approaches
aligned
with
principles
green
sustainable
chemistry,
several
interesting
papers
covering
photocatalytic
difunctionalization
also
published
decade.
This
particular
field
really
attracted
That
why
we
decided
compile
review
article
articles
related
under
conditions.
Here
review,
categorized
discussed
three
categories,
namely
i)
without
using
any
catalyst,
ii)
organocatalysts,
iii)
metal
catalysts
deeper
understanding
key
aspects
these
transformations.
Язык: Английский
Photoredox/Palladium-Catalyzed Reduction Alkylation of Imines and Ammonium Salts via Dual C–N Bond Cleavage
The Journal of Organic Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Апрель 16, 2025
Here,
we
report
a
photoredox/palladium-catalyzed
reduction
alkylation
of
imines
and
ammonium
salts
via
dual
C-N
cleavage.
This
reaction
proceeds
under
mild,
green,
operationally
simple
conditions,
offering
broad
scope
secondary
amine
compounds
with
alpha
quaternary
carbon.
Mechanistic
studies
indicate
that
the
α-amino
carbanion,
generated
by
successive
single-electron
transfer
process,
is
key
intermediate
in
photoredox/palladium
catalysis.
Язык: Английский