The Chemical Record,
Год журнала:
2023,
Номер
23(9)
Опубликована: Янв. 5, 2023
Abstract
Fluorine‐containing
molecules
have
attracted
much
attention
in
medicinal,
agrochemical,
and
materials
sciences
because
they
offer
unique
physical
biological
properties.
Therefore,
many
efficient
fluorination
reactions
been
developed
over
the
years.
Recent
advancements
chemistry
expanded
range
of
substrates,
regioselectivity/stereoselectivity
control
has
also
achieved.
Ring‐opening
is
an
method
to
construct
complex
fluorine‐containing
with
diversity,
starting
from
simple
cyclic
compounds.
This
review
aims
summarize
developments
ring‐opening
fluorination,
particularly
larger‐sized
Fluorine
introduction
bond
cleavage
compounds
such
as
carbocycles,
heterocycles,
aromatics
provide
access
that
are
difficult
be
synthesized
by
conventional
methods.
Chemical Communications,
Год журнала:
2022,
Номер
58(67), С. 9409 - 9412
Опубликована: Янв. 1, 2022
Sulfonyl
fluorides
are
emerging
as
key
structural
motifs
in
organic
synthesis,
medicinal
chemistry,
and
materials
science.
Herein
we
report
two
efficient
complementary
methods
for
direct
decarboxylative
fluorosulfonylation
of
carboxylic
acids
by
the
merging
copper
catalysis
with
different
N-centered
HAT
regents.
A
wide
range
structurally
diverse
sulfonyl
was
readily
accessed
from
primary,
secondary,
tertiary
a
single
step
under
mild
conditions.
Angewandte Chemie International Edition,
Год журнала:
2023,
Номер
62(40)
Опубликована: Авг. 4, 2023
A
series
of
mesoionic,
1,2,3-triazole-derived
N-heterocyclic
olefins
(mNHOs),
which
have
an
extraordinarily
electron-rich
exocyclic
CC-double
bond,
was
synthesized
and
spectroscopically
characterized,
in
selected
cases
by
X-ray
crystallography.
The
kinetics
their
reactions
with
arylidene
malonates,
ArCH=C(CO2
Et)2
,
gave
zwitterionic
adducts,
were
investigated
photometrically
THF
at
20
°C.
resulting
second-order
rate
constants
k2
(20
°C)
correlate
linearly
the
reported
electrophilicity
parameters
E
malonates
(reference
electrophiles),
thus
providing
nucleophile-specific
N
sN
mNHOs
according
to
correlation
lg
°C)=sN
(N+E).
With
21
The Journal of Organic Chemistry,
Год журнала:
2023,
Номер
88(11), С. 7431 - 7447
Опубликована: Май 23, 2023
Three-component
selenofunctionalization
processes
of
olefins,
diselenides
and
sulfonamides,
water,
alcohols,
or
acids
utilizing
1-fluoropyridinium
triflate
(FP-OTf)
as
a
reaction
promoter
are
reported.
Under
the
optimal
conditions,
broad
range
vicinally
functionalized
selenide
derivatives
was
accessible
with
high
yields
excellent
functional
group
compatibilities.
Mechanistic
studies
revealed
that
FP-OTf
played
key
role
in
this
process.
European Journal of Organic Chemistry,
Год журнала:
2025,
Номер
28(5)
Опубликована: Янв. 3, 2025
Abstract
Fluorinated
molecules
are
core
to
contemporary
drug
discovery
programs
and
critical
for
advancing
innovation
in
numerous
fields.
In
merging
these
important
chemical
themes,
fluorinated
Diels‐Alder
cycloaddition
products
a
particularly
attractive
subset
of
compounds
with
significant
utility.
Herein,
an
in‐depth
computational
experimental
study
fluorine
substitution
effects
on
dienophile
partners
reactions
is
reported.
Of
particular
focus
this
understanding
the
origin
reaction
rate
deceleration
as
consequence
employing
dienophiles
factors
controlling
endo‐
vs.
exo
‐selectivity.
To
unlock
insight
into
unique
reactivity,
density
function
theory
calculations,
distortion/interaction‐activation
strain
models,
energy
decomposition
analysis
natural
bond
orbital
analysis,
among
other
methods,
were
applied.
addition,
influence
oriented
external‐electric‐field‐effects
(OEEFs)
local
electric
field
explored.
further
probe
effect,
studies
charge‐enhanced
reactivity
conducted.
Collectively,
work
offers
novel
mechanistic
pertinent
providing
valuable
scaffolds.
The Chemical Record,
Год журнала:
2025,
Номер
unknown
Опубликована: Янв. 16, 2025
Abstract
Selectfluor,
[1‐chloromethyl‐4‐fluoro‐1,4‐diazoniabicyclo[2.2.2]octane
bis(tetrafluoroborate)],
is
a
highly
valuable
reagent
in
contemporary
chemistry,
serving
not
only
as
an
electrophilic
fluorinating
agent
but
also
effective
catalyst
the
synthesis
of
various
pharmaceutically
relevant
heterocycles.
This
review
article
seeks
to
present
comprehensive
overview
significant
heterocyclic
ring
formations
facilitated
by
selectfluor.
Both
metal‐free
and
metal‐catalyzed
recent
advancement
on
selectfluor
mediated
cyclisation
processes
are
discussed
this
mainly
over
last
eight
years
(2017‐April
2024).
The Journal of Organic Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Март 13, 2025
The
biaryl
motif
is
important
in
many
fields
within
chemistry
and
the
life
sciences.
Thus,
better
strategies
to
forge
aryl–aryl
bonds
are
valuable.
Herein,
we
report
conditions
permitting
room
temperature
arylation
of
N-aryl
amide
substrates,
using
ubiquitous
aryl
boronic
acid
reagents.
Critical
success
this
method
use
Selectfluor
as
a
sustainable
alternative
oxidant
silver-based
additives
deployment
bulky
QuinOx
ligand
supporting
palladium
catalyst.
We
herein
disclose
the
first
example
of
metal-free,
redox-umpolung-enabled
catalytic
fluorination
α-branched
ketones
with
nucleophilic
fluorine
by
judicious
choice
an
oxidant.
The
strategic
use
cyclopropyl
malonoyl
peroxide
in
hypervalent
iodine(III)
catalysis
expands
modularity
and
generality
construction
α-fluorinated
ideally
orthogonal
reactivity
space,
avoiding
competing
oxidation
processes.
Characteristic
for
this
transformation
is
its
operational
simplicity,
mild
reaction
conditions,
gram-scale
synthetic
ability.
ACS Catalysis,
Год журнала:
2023,
Номер
13(7), С. 4391 - 4397
Опубликована: Март 16, 2023
Reported
herein
is
the
fluorination
of
α-imino
gold
carbenes,
generated
in
situ
from
azidoalkynes,
to
access
substituted
C3-fluorinated
quinolones
and
indoles.
The
methodology
has
been
applied
for
synthesizing
quinolone-
quinoline-based
natural
products,
including
pseudanes
(4
representative
examples),
chimanine
A,
graveolinine.
Mechanistic
investigations,
NMR
SC-XRD
analysis,
reveal
that
NEt3·3HF
reacts
with
catalyst
generate
a
phosphine-ligated
fluoride-bridged
binuclear
complex
which
then
generates
active
this
reaction.
