ACS Catalysis,
Год журнала:
2024,
Номер
14(9), С. 6513 - 6524
Опубликована: Апрель 13, 2024
Efficient
synthesis
of
sulfonamides
has
long
been
pursued
by
chemists
due
to
their
frequent
occurrence
in
pharmaceuticals,
especially
anti-inflammatory
medicines.
The
traditional
assembly
from
sulfonyl
chlorides
and
amines,
as
well
the
recently
developed
one-step
involving
sulfur
dioxide,
still
faces
challenges
such
poor
substrate
compatibility
and/or
stringent
reaction
conditions.
Herein,
we
present
a
strategy
for
situ
generation
sulfamoyl
radicals
modular
both
alkenyl
alkyl
with
wide
applicability
(>100
examples),
mild
conditions,
easily
accessible
starting
materials.
This
method
is
successfully
applied
late-stage
modification
drug
molecules
(23
molecule
naratriptan,
15N-labeling
sulfonamides.
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.
ACS Catalysis,
Год журнала:
2023,
Номер
13(22), С. 14503 - 14512
Опубликована: Окт. 27, 2023
Sulfur(VI)
fluoride
exchange
(SuFEx)
click
chemistry
provides
a
powerful
tool
for
the
rapid
assembly
of
modular
connections.
Herein,
we
report
an
organocatalytic
SuFEx
reaction
sulfonyl
fluorides,
fluorosulfates,
and
sulfamoyl
fluorides.
Under
catalysis
10
mol
%
N-heterocyclic
carbene
(NHC),
or
under
relay
NHC
HOBt,
different
SuFExable
hubs
efficiently
undergo
reactions
with
alcohols
amines
to
afford
sulfonates,
sulfonamides,
sulfates,
sulfamates,
sulfamides
in
49–99%
yields.
More
than
190
sulfonylated
products,
including
25
natural
product
derivatives,
have
been
prepared
through
this
method.
Mechanism
study
showed
that
NHCs
might
act
as
carbon-centered
Broønsted
base
activate
formation
hydrogen
bonding.
Organic Chemistry Frontiers,
Год журнала:
2023,
Номер
11(1), С. 217 - 235
Опубликована: Ноя. 14, 2023
This
review
summarizes
the
latest
achievements
in
photochemical
and
electrochemical
strategies
for
synthesis
of
sulfonyl
fluorides
focuses
on
novel
features
proposed
mechanisms.
Nature Communications,
Год журнала:
2023,
Номер
14(1)
Опубликована: Авг. 24, 2023
Sulfonyl
and
sulfonimidoyl
fluorides
are
versatile
substrates
in
organic
synthesis
medicinal
chemistry.
However,
they
have
been
exclusively
used
as
S(VI)+
electrophiles
for
defluorinative
ligations.
Converting
sulfonyl
to
S(VI)
radicals
is
challenging
underexplored
due
the
strong
bond
dissociation
energy
of
SVI-F
high
reduction
potentials,
but
once
achieved
would
enable
dramatically
expanded
synthetic
utility
downstream
applications.
In
this
report,
we
disclose
a
general
platform
address
issue
through
cooperative
organosuperbase
activation
photoredox
catalysis.
Vinyl
sulfones
sulfoximines
obtained
with
excellent
E
selectivity
under
mild
conditions
by
coupling
reactions
alkenes.
The
method
preparation
functional
polymers
dyes
also
demonstrated.
Catalysis Science & Technology,
Год журнала:
2023,
Номер
13(9), С. 2597 - 2617
Опубликована: Янв. 1, 2023
Fluorosulfonylation
of
(hetero)aromatic
and
aliphatic
compounds
with
emphasis
on
the
use
fluorosulfonylating
hubs
is
discussed.
Examples
click
chemistry
(SuFEx)
reactions
diversity
oriented
clicking
(DOC)
processes
are
provided.
Organic Letters,
Год журнала:
2023,
Номер
25(17), С. 3109 - 3113
Опубликована: Апрель 21, 2023
An
electron
donor-acceptor
(EDA)
complex
photoactivation
strategy
for
radical
fluorosulfonylation
is
disclosed
the
first
time.
Simply
upon
blue
light
irradiation,
FSO2
can
be
generated
efficiently
under
catalyst-free,
base-free,
and
additive-free
conditions,
which
enables
facile
access
to
6-keto
alkenylsulfonyl
fluorides
from
readily
available
propargyl
alcohols
FSO2Cl.
The
fluoride
motif
has
been
showcased
as
a
versatile
SuFEx
hub
with
diverse
follow-up
derivatizations.
Organic Letters,
Год журнала:
2023,
Номер
25(24), С. 4478 - 4482
Опубликована: Июнь 12, 2023
Multicomponent
reactions
represent
a
powerful
method
for
building
complex
molecules
from
structurally
simple
starting
materials.
Herein,
we
report
novel
three-component
radical–polar
crossover
reaction
involving
tandem
addition
of
two
different
olefins,
which
is
initiated
by
the
selective
fluorosulfonyl
radicals
to
alkyl
alkenes.
This
process
provides
facile
and
effective
access
multiple
functionalized
aliphatic
sulfonyl
fluoride
molecules.
Further
transformation
products
also
demonstrated.
