Angewandte Chemie International Edition,
Journal Year:
2021,
Volume and Issue:
60(40), P. 22035 - 22042
Published: Aug. 12, 2021
Sulfonyl
fluorides
have
widespread
applications
in
many
important
fields,
including
ligation
chemistry,
chemical
biology,
and
drug
discovery.
Therefore,
new
methods
to
increase
the
synthetic
efficiency
expand
available
structures
of
sulfonyl
are
highly
demand.
Here,
we
introduce
a
powerful
class
fluoride
hubs,
β-chloro
alkenylsulfonyl
(BCASF),
which
can
be
constructed
via
radical
chloro-fluorosulfonyl
difunctionalization
alkynes
under
photoredox
conditions.
BCASF
molecules
exhibit
versatile
reactivities
well
undergo
series
transformations
at
chloride
site
while
keeping
group
intact,
reduction,
Suzuki
coupling,
Sonogashira
as
nucleophilic
substitution
with
various
nitrogen,
oxygen,
sulfur
nucleophiles.
By
using
hub,
wide
range
becomes
readily
accessible,
such
cis
fluorides,
dienylsulfonyl
ynenylsulfonyl
challenging
or
even
not
possible
synthesize
before
known
methods.
Moreover,
further
application
late-stage
modification
peptides
drugs
is
also
demonstrated.
Organic Letters,
Journal Year:
2023,
Volume and Issue:
25(4), P. 581 - 586
Published: Jan. 25, 2023
A
practical
electrochemically
driven
method
for
fluorosulfonylation
of
both
aryl
and
alkyl
thianthrenium
salts
has
been
disclosed.
The
strategy
does
not
need
external
redox
reagents
or
metal
catalysts.
In
combination
with
C-H
thianthrenation
aromatics,
this
provides
a
new
tool
the
site-selective
drugs.
Green Chemistry,
Journal Year:
2024,
Volume and Issue:
26(6), P. 3435 - 3440
Published: Jan. 1, 2024
A
practical
electrosynthesis
of
aryl
sulfonyl
fluorides
from
nitroarenes
is
described.
Cheap
N
-methylimidazolium
p
-toluenesulfonate
has
been
found
to
be
an
effective
additive,
promoting
the
desired
fluorosulfonylation
under
very
mild
conditions.
ACS Catalysis,
Journal Year:
2024,
Volume and Issue:
14(5), P. 3115 - 3127
Published: Feb. 13, 2024
Although
the
transition
metal-catalyzed
radical
fluorine
atom
transfer
(FAT)
strategy
has
emerged
as
a
powerful
tool
for
construction
of
C–F
bonds,
to
our
knowledge,
this
approach
rarely
been
applied
formation
S–F
bonds.
Here,
we
report
that
4-methoxypyridine
1-oxide
can
serve
an
inexpensive
and
simple
yet
effective
ligand
thus
promote
transformation
copper-mediated
challengeable
FAT
sulfonyl
radicals,
paving
way
assembly
FSO2
group.
Based
on
concept,
three
Cu(I)-catalyzed
protocols
involving
site-selective
intra-
intermolecular
fluorosulfonylation
inert
C(sp3)–H
bonds
1,2-aminofluorosulfonylation
inactivated
alkenes
have
developed,
enabling
preparation
C(sp3)-rich
aliphatic
fluorides
cannot
be
easily
synthesized
by
known
methods.
These
practical
operationally
methods
result
in
high
functional
group
tolerance
under
mild
conditions
modification
bioactive
derivatives
highly
valued
molecules.
Detailed
mechanistic
studies
indicate
unique
role
facilitating
such
rare
FATs
via
outer-sphere
pathway.
Organic Letters,
Journal Year:
2020,
Volume and Issue:
22(6), P. 2281 - 2286
Published: March 2, 2020
We
report
herein
a
general
and
practical
copper-catalyzed
fluorosulfonylation
reaction
of
wide
range
abundant
arenediazonium
salts
to
smoothly
prepare
various
arenesulfonyl
fluorides
using
the
1,4-diazabicyclo[2.2.2]octane-bis(sulfur
dioxide)
adduct
as
convenient
sulfonyl
source
in
combination
with
KHF2
an
ideal
fluorine
without
need
for
additional
oxidants.
Interestingly,
electronic
character
arene
ring
starting
has
significant
impact
on
mechanistic
pathway.
Organic Letters,
Journal Year:
2020,
Volume and Issue:
22(11), P. 4389 - 4394
Published: May 27, 2020
A
method
to
activate
sulfamoyl
fluorides,
fluorosulfates,
and
sulfonyl
fluorides
with
calcium
triflimide
DABCO
for
SuFEx
amines
is
described.
The
reaction
was
applied
a
diverse
set
of
sulfamides,
sulfamates,
sulfonamides
at
room
temperature
under
mild
conditions.
Additionally,
we
highlight
this
transformation
parallel
medicinal
chemistry
generate
broad
array
nitrogen-based
S(VI)
compounds.
Angewandte Chemie International Edition,
Journal Year:
2020,
Volume and Issue:
59(19), P. 7494 - 7500
Published: March 11, 2020
Abstract
SuFEx
reactions,
in
which
an
S−F
moiety
reacts
with
a
silyl‐protected
phenol,
have
been
developed
as
powerful
click
reactions.
In
the
current
paper
we
open
up
potential
of
reactions
enantioselective
analyze
role
Si
and
outline
mechanism
this
reaction.
As
result,
fast,
high‐yielding,
“Si‐free”
enantiospecific
sulfonimidoyl
fluorides
developed,
their
shown,
by
both
experimental
theoretical
methods,
to
yield
chiral
products.
European Journal of Organic Chemistry,
Journal Year:
2021,
Volume and Issue:
2021(47), P. 6478 - 6510
Published: Sept. 8, 2021
Abstract
Current
medicinal
chemistry
relies
heavily
on
the
quality
of
building
blocks,
i.
e.
reagents
used
to
introduce
chemical
diversity
into
target
molecules.
The
last
decade
witnessed
an
emergence
many
novel
(or
well‐overlooked
old)
chemotypes
for
drug
discovery,
which
is
related
adapting
new
synthetic
methodologies,
designing
sp
3
‐enriched
bioisosteres,
paying
attention
previously
underrated
even
unwanted)
structural
motifs,
or
combination
thereof.
In
this
review
with
532
references,
a
survey
selected
that
emerged
recently
in
provided,
focus
synthesis
corresponding
blocks.
Thus,
saturated
(hetero)aliphatic
boronates,
sulfonyl
fluorides,
sulfinates,
non‐classical
benzene
isosteres,
bicyclic
morpholine/piperidine/piperazine
analogs,
as
well
gem
‐difluorinated
cycloalkanes
(as
example
emerging
fluorinated
motifs)
are
discussed.
Organic Letters,
Journal Year:
2019,
Volume and Issue:
21(21), P. 8673 - 8678
Published: Oct. 22, 2019
A
visible-light-mediated
deaminative
thioesterification
of
amino
acid
derived
Katritzky
salts
with
thiobenzoic
has
been
developed,
which
provides
a
novel
synthetic
method
for
the
synthesis
α-mercapto
derivatives
under
mild
conditions.
This
photoredox
catalyst-free
generation
alkyl
radicals
via
C-N
bond
cleavage
is
enabled
by
formation
an
electron-donor-acceptor
(EDA)
complex
between
salt
and
anion,
represents
new
entry
EDA
chemistry.
