Chinese Journal of Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Март 20, 2025
Comprehensive
Summary
The
reaction
site
of
aryl
diazonium
salt
was
restricted
in
the
position
moiety,
due
to
intrinsic
electrophilicity
moiety.
Herein,
we
described
an
unprecedented
chemoselective
alkylation
Csp
2
‐H
salts
with
1‐iodo‐3‐pentafluorosulfanylbicyclo[1,1,1]pentane
(SF
5
‐BCP‐I).
This
novel
provided
efficient
access
various
SF
‐BCP
substituted
aromatics
that
might
have
great
potential
application
drug
discovery.
Mechanistic
experiments
and
theoretical
studies
revealed
electrophilic
radical
resulted
thermodynamic
favorable
addition
on
rather
than
moiety
salt.
Nature Communications,
Год журнала:
2024,
Номер
15(1)
Опубликована: Ноя. 9, 2024
Fluorinated
or
fluoroalkylated
alcohols
are
common
structural
motifs
in
biologically
active
molecules,
natural
products,
and
pharmaceuticals.
However,
pentafluorosulfanyl
(SF
Chemistry - A European Journal,
Год журнала:
2025,
Номер
unknown
Опубликована: Янв. 15, 2025
The
pentafluorosulfanyl
(SF5-)
group
has
been
the
subject
of
a
surge
interest
in
past
decade,
but
there
is
still
little
practicality
associated
with
its
synthesis
and
installation.
Herein
reported
first
continuous
flow
chloride
(SF5Cl),
most
common
reagent
for
SF5-substituted
compounds.
based
on
inexpensive
easy-to-handle
reagents:
sulfur
powder
(S8),
trichloroisocyanuric
acid
(TCCA)
potassium
fluoride
(KF).
To
this
end,
custom-made
stirring
reactor
was
designed
to
allow
fast,
safe,
highly
efficient
on-demand
SF5Cl.
resulting
SF5Cl
solution
showcased
radical
addition
alkynes
telescoped
fashion.
Herein
for
the
first
time,
we
disclose
a
practical
and
straightforward
approach
to
access
α-SF5
ketones
via
direct
oxypentafluorosulfanylation
of
alkynes
with
SF5Cl
oxygen
under
acidic
conditions
by
one
step.
The
protocol
features
mild
reaction
conditions,
broad
substrate
scope,
good
functional
group
compatibility
can
be
applied
late-state
functionalization
complex
natural
products
pharmaceuticals.
A
radical
mechanism
involving
SF5
addition
triple
bonds
followed
O2
capture
is
proposed.
Chinese Journal of Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Март 20, 2025
Comprehensive
Summary
The
reaction
site
of
aryl
diazonium
salt
was
restricted
in
the
position
moiety,
due
to
intrinsic
electrophilicity
moiety.
Herein,
we
described
an
unprecedented
chemoselective
alkylation
Csp
2
‐H
salts
with
1‐iodo‐3‐pentafluorosulfanylbicyclo[1,1,1]pentane
(SF
5
‐BCP‐I).
This
novel
provided
efficient
access
various
SF
‐BCP
substituted
aromatics
that
might
have
great
potential
application
drug
discovery.
Mechanistic
experiments
and
theoretical
studies
revealed
electrophilic
radical
resulted
thermodynamic
favorable
addition
on
rather
than
moiety
salt.
