Organic Letters,
Год журнала:
2023,
Номер
25(21), С. 3910 - 3915
Опубликована: Май 24, 2023
An
efficient
aminofluorosulfonylation
strategy
was
developed
for
the
synthesis
of
various
pyrazoline-functionalized
aliphatic
sulfonyl
fluorides
using
β,γ-unsaturated
hydrazones
with
sulfur
dioxide
and
NFSI
as
starting
materials
under
mild
conditions.
The
fluoride
products
could
be
successfully
transformed
into
corresponding
sulfonate
esters
amides
via
sulfur(VI)
exchange
(SuFEx)
click
reactions.
Preliminary
mechanistic
investigations
demonstrate
that
reaction
operates
through
a
radical
cyclization/SO2
insertion/fluorination
cascade
process.
National Science Review,
Год журнала:
2023,
Номер
10(6)
Опубликована: Апрель 29, 2023
Abstract
Sulfur
fluoride
exchange
(SuFEx),
a
new
generation
of
click
chemistry,
was
first
presented
by
Sharpless,
Dong
and
co-workers
in
2014.
Owing
to
the
high
stability
yet
efficient
reactivity
SVI–F
bond,
SuFEx
has
found
widespread
applications
organic
synthesis,
materials
science,
chemical
biology
drug
discovery.
A
diverse
collection
linkers
emerged,
involving
gaseous
SO2F2
SOF4
hubs;
SOF4-derived
iminosulfur
oxydifluorides;
O-,
N-
C-attached
sulfonyl
fluorides
sulfonimidoyl
fluorides;
novel
sulfondiimidoyl
fluorides.
This
review
summarizes
progress
these
connectors,
with
an
emphasis
on
analysing
advantages
disadvantages
synthetic
strategies
connectors
based
concept,
it
is
expected
be
beneficial
researchers
rapidly
correctly
understand
this
field,
thus
inspiring
further
development
chemistry.
Nature Communications,
Год журнала:
2022,
Номер
13(1)
Опубликована: Июнь 11, 2022
Abstract
Sulfonyl
fluorides
have
attracted
considerable
and
growing
research
interests
from
various
disciplines,
which
raises
a
high
demand
for
novel
effective
methods
to
access
this
class
of
compounds.
Radical
flurosulfonylation
is
recently
emerging
as
promising
approach
the
synthesis
sulfonyl
fluorides.
However,
scope
applicable
substrate
reaction
types
are
severely
restricted
by
limited
known
radical
reagents.
Here,
we
introduce
solid
state,
redox-active
type
fluorosulfonyl
reagents,
1-fluorosulfonyl
2-aryl
benzoimidazolium
triflate
(FABI)
salts,
enable
fluorosulfonylation
olefins
under
photoredox
conditions.
In
comparison
with
precursor,
gaseous
FSO
2
Cl,
FABI
salts
bench-stable,
easy
handle,
affording
yields
in
before
challenging
substrates.
The
advantage
FABIs
further
demonstrated
development
an
alkoxyl-fluorosulfonyl
difunctionalization
olefins,
forges
facile
useful
β-alkoxyl
related
compounds,
would
thus
benefit
study
context
chemical
biology
drug
discovery
future.
Organic Letters,
Год журнала:
2022,
Номер
24(20), С. 3702 - 3706
Опубликована: Май 17, 2022
Electrochemical
synthesis
of
versatile
β-keto
sulfonyl
fluorides
is
accomplished
by
radical
fluorosulfonylation
vinyl
triflates
with
FSO2Cl
as
the
fluorosulfonyl
source.
This
electroreductive
protocol
uses
inexpensive
graphite
felt
electrodes,
thus
avoiding
use
a
sacrificial
anode.
Moreover,
this
protocol,
featuring
metal-free,
mild
conditions
and
easy
scalability,
allows
expedient
access
to
valuable
from
readily
available
precursors,
well
cyclic
ones
that
are
otherwise
inaccessible
using
prior
methods.
Chemistry - A European Journal,
Год журнала:
2023,
Номер
29(33)
Опубликована: Март 24, 2023
Sulfur(VI)-fluoride
exchange
linkage
as
a
next
generation
of
click
chemistry
was
introduced
by
Sharpless
and
coworkers
in
2014.
Distinguished
from
CuAAC,
the
SuFEx
reaction
proceeds
under
metal-free
conditions,
reactive
linkers
are
variable,
enabling
access
to
diverse
class
compounds.
Therein,
series
emerged
has
been
widely
prevalent
fields.
The
SVI
-F
bond
comparison
-Cl
features
excellent
stability
chemoselectivity.
primarily
involves
formation
S-O
S-N
bonds
via
commercially
available
phenols
amines,
yet
less
study
on
C-SuFEx
linkage.
This
review
will
focus
three
types
for
comprising
S-O,
S-N,
S-C
bonds,
we
hope
provide
practical
guidance
chemistry.
Journal of the American Chemical Society,
Год журнала:
2023,
Номер
145(38), С. 20767 - 20774
Опубликована: Сен. 18, 2023
Sulfinates
are
important
lynchpin
intermediates
in
pharmaceutical
production;
however,
their
synthesis
via
photoredox
catalysis
is
challenging
because
of
facile
oxidation.
We
herein
disclose
a
photocatalytic
strategy
for
the
direct
conversion
alcohols
and
alkyl
bromides
into
sulfinates.
These
transformations
enabled
by
utilization
easily
oxidized
radical
precursors─namely,
alcohol
N-heterocyclic
carbene
adducts
N-adamantyl
aminosupersilane─that
facilitate
efficient
oxidatively
labile
sulfinate
products.
A
broad
range
functional
groups
amenable
to
reported
transformations,
providing
rapid
access
sulfonamides,
sulfonyl
halides,
sulfones,
sulfonic
acids.
The
utility
these
methods
further
demonstrated
late-stage
diversification
natural
products
drugs
pharmaceutically
relevant
sulfonamides
"clickable"
fluorides.
In
summary,
this
work
illustrates
potential
novel
precursors
expand
breadth
transformations.
European Journal of Organic Chemistry,
Год журнала:
2024,
Номер
27(23)
Опубликована: Май 25, 2024
Abstract
Sulfonyl
fluorides
have
widespread
applications
in
many
fields,
including
organic
synthesis,
chemical
biology,
drug
discovery
and
materials
science.
In
particular,
the
past
decade,
a
number
of
aliphatic
sulfonyl
been
identified
showing
various
biological
activities.
These
appealing
features
brought
about
significant
advancement
developing
synthetic
methods
to
access
fluorides.
this
review,
we
will
discuss
recent
developments
radical
approaches
for
synthesis
