Catalytic difluorocarbene insertion enables access to fluorinated oxetane isosteres
Nature Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Фев. 20, 2025
Язык: Английский
Regio- and Diastereoselective Cascade Reactions of Bicyclo[1.1.0]butanes: Access to gem-Difluorinated Carbocyclic Rings
Organic Letters,
Год журнала:
2025,
Номер
unknown
Опубликована: Апрель 17, 2025
gem-Difluorinated
carbocyclic
rings
are
attractive
motifs
in
drug
development.
Herein,
we
report
the
transition-metal
free
cascade
reaction
of
bicyclo[1.1.0]butanes
(BCBs)
with
gem-difluorocyclopropenes
for
synthesis
gem-difluorinated
excellent
regio-
and
diastereoselectivity.
This
method
was
successfully
applied
to
provide
a
broad
range
cyclopentenes
cyclopropanes,
which
could
undergo
variety
difluoromethylene
(CF2)
retaining
transformations.
Язык: Английский
Trendbericht: Organische Chemie 2025
Nachrichten aus der Chemie,
Год журнала:
2025,
Номер
73(3), С. 40 - 70
Опубликована: Фев. 28, 2025
Abstract
Highlights
von
November
2023
bis
2024:
die
erste
Einelektron‐C–C‐σ‐Bindung
und
Anti‐Bredt‐Verbindung;
gesättigte
Heterocyclen
elektrochemisch
funktionalisieren;
Ausrichten
diskotischer
Flüssigkristalle;
enantioselektive
Wagner‐Meerwein‐Umlagerung
reiner
Aliphaten;
photokatalytisch
Furanen
zu
Pyrrolen;
mit
Ammoniak
primären
Arylaminen;
Metallschrott
recyceln
ionischen
Flüssigkeiten;
terminale
Alkene
Ni‐Katalysatoren
zum
(Z)‐
oder
(E)‐Alken
isomerisieren;neue
Fungizide,
Medikamente
Alkaloide.
(3+2) Annulation of Donor–Acceptor Cyclopropanes with Difluoroenoxysilanes: Syntheses of gem-Difluorocyclopentenes via α,α-Difluoroketone Scaffolds
The Journal of Organic Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Март 27, 2025
Herein,
we
present
an
acid-
and
base-mediated
approach
for
ring
opening
of
donor-acceptor
cyclopropanes
(DACs)
followed
by
(3+2)
annulation,
yielding
biologically
relevant
gem-difluorinated
cyclopentenes
via
α,α-difluoroketone
scaffolds.
Fluorinated
rings
are
essential
building
blocks
in
drug
discovery
materials
research.
This
methodology
has
a
broad
substrate
scope,
is
scalable,
provides
practical
synthetic
route
to
obtain
value-added
fluorinated
compounds.
Язык: Английский
Gem-difluorinative ring-expansion of alkenes
Опубликована: Апрель 18, 2024
Incorporating
fluorine
into
aliphatic
rings
induces
significant
alterations
in
molecular
conformation,
acidity/basicity,
and
lipophilicity.
Current
methods
for
synthesizing
fluorinated
rings,
however,
involve
manipulating
functional
groups
within
pre-existing
ring
systems.
Here,
we
have
developed
a
novel
chemical
reaction
-
gem-difluorinative
ring-expansion
of
methylenecycloalkanes.
The
involves
iodine(III)
species,
allows
the
preparation
gem-difluorinated
macrocyclic,
fused,
spiro,
bridged,
natural
product-derived
structures.
protocol's
practicality
is
demonstrated
through
several
decagram-scale
syntheses.
Язык: Английский
Enantioselective Access to β,β-Difluorinated Carbocycles
Synfacts,
Год журнала:
2024,
Номер
20(07), С. 0745 - 0745
Опубликована: Июнь 14, 2024
Key
words
difluorination
-
hypervalent
iodine
difluorinated
carbocycles
Язык: Английский
1.7 Synthesis of Difluoromethylene-Containing Compounds
Опубликована: Янв. 1, 2024
Abstract
The
difluoromethylene
group
(CF2)
is
a
valuable
fluorinated
motif
that
widely
present
in
pharmaceuticals,
agrochemicals,
and
advanced
functional
materials
because
of
the
unique
properties
fluorine
atoms.
Consequently,
considerable
efforts
have
been
dedicated
to
introducing
into
organic
molecules.
This
review
summarizes
progress
synthesis
difunctionalized
difluoromethane
(R1−CF2−FG)
compounds,
including
methods
for
difluoroalkylation
C—X
unsaturated
bonds,
gem-difluorination
reactions.
Язык: Английский