Abstract
A
palladium-catalyzed
one-pot
amino-sulfonylation
of
aryl
iodide
derivatives
with
thiourea
dioxide,
PdCl2dppf,
and
added
hydroxylamine-O-sulfonic
acid
is
presented.
This
gave
structure
diversity
to
primary
sulfonamides
features
good
functional
group
compatibility,
mild
reaction
conditions,
excellent
regioselectivity,
moderate
yields.
The
robustness
potential
this
method
have
also
been
successfully
demonstrated
by
late-stage
elaboration
gram-scale
reaction.
approach
achieves
the
divergent
construction
complex
core
structures
that
are
prevalent
in
highly
valuable
natural
products
such
as
Sulpiride,
Venetoclax,
Furosemide.
Chemical Communications,
Год журнала:
2020,
Номер
56(30), С. 4145 - 4155
Опубликована: Янв. 1, 2020
Recently,
sulfonylation
reactions
using
potassium/sodium
metabisulfite
as
the
sulfur
dioxide
surrogate
have
been
developed
rapidly.
In
most
cases,
transformations
go
through
radical
processes
with
insertion
of
under
mild
conditions.
Additionally,
transition
metal
catalysis
is
applied
in
for
synthesis
sulfonyl-containing
compounds.
Among
approaches,
photoinduced
conversions
visible
light
or
ultraviolet
irradiation
are
also
involved.
this
updated
report,
from
potassium
sodium
summarized.
ACS Catalysis,
Год журнала:
2021,
Номер
11(7), С. 4169 - 4204
Опубликована: Март 19, 2021
Arylsulfonyl
compounds
are
among
the
most
important
in
pharmaceutical
and
medicinal
chemistry.
Hence,
a
wide
variety
of
sulfonylation
methods
have
been
reported
recently.
This
review
summarizes
arylsulfonylation
methodologies
developed
last
5
years
includes
two
major
categories.
The
first
entails
direct
second
multicomponent
arylsulfonylation.
In
arylsulfonylation,
arylsulfonyl
reagents
react
with
C–H
activated
compounds,
alkynes,
alkenes
through
coupling
or
addition
reactions.
reactions,
arylation
various
substrates
sulfur
dioxide
surrogates,
such
as
DABSO,
Na2S2O5,
K2S2O5.
hydrazides,
aryl
boronic
acids,
silanes,
halides
widely
employed
that
surrogates
to
generate
an
source,
ensuing
reactions
proceed
via
pathways
analogous
those
Organic & Biomolecular Chemistry,
Год журнала:
2021,
Номер
19(7), С. 1459 - 1482
Опубликована: Янв. 1, 2021
This
review
presents
the
metal-catalyzed
C–S
bond-formation
reaction
to
access
organosulfur
compounds
using
various
sulfur
surrogates
with
an
extended
discussion
on
mechanism,
regioselectivity
of
product
and
pharmaceutical
application.
Angewandte Chemie International Edition,
Год журнала:
2020,
Номер
60(13), С. 7397 - 7404
Опубликована: Дек. 18, 2020
Abstract
A
broad‐spectrum,
catalytic
method
has
been
developed
for
the
synthesis
of
sulfonamides
and
sulfamates.
With
activation
by
combination
a
amount
1‐hydroxybenzotriazole
(HOBt)
silicon
additives,
amidations
sulfonyl
fluorides
fluorosulfates
proceeded
smoothly
excellent
yields
were
generally
obtained
(87–99
%).
Noticeably,
this
protocol
is
particularly
efficient
sterically
hindered
substrates.
Catalyst
loading
low
only
0.02
mol
%
catalyst
required
multidecagram‐scale
an
amantadine
derivative.
In
addition,
potential
in
medicinal
chemistry
demonstrated
marketed
drug
Fedratinib
via
key
intermediate
fluoride
13
.
Since
large
number
amines
are
commercially
available,
route
provides
facile
entry
to
access
analogues
biological
screening.
The Chemical Record,
Год журнала:
2021,
Номер
21(12), С. 3338 - 3355
Опубликована: Янв. 26, 2021
Abstract
Sulfonyl
compounds
have
attracted
considerable
interest
due
to
their
extensive
applications
in
drug
discovery,
agricultural,
and
material
science.
The
access
the
assembly
of
SO
2
‐containing
via
same
oxidative‐state
introduction
hypervalent
sulfur
has
come
fore
recent
years.
Especially,
transition‐metal‐involved
synthesis
is
most
effective
strategy
since
easy
insert
into
metal‐carbon
bonds.
This
review
discusses
application
oxidation‐state
under
transition‐metal‐catalyzed
conditions,
presents
according
different
metal
catalysts
synthesized
diversity
sulfur‐containing
skeletons,
including
sulfonamides,
sulfones,
sulfinamides,
sulfonyl
acids
fluorides.
Chemical Science,
Год журнала:
2021,
Номер
12(18), С. 6429 - 6436
Опубликована: Янв. 1, 2021
Sulfonamides
are
now
accessible
directly
from
carboxylic
acids
by
a
one-step,
tricomponent
decarboxylative
amidosulfonation
that
provides
the
missing
link
between
two
key
functionalities.
Angewandte Chemie International Edition,
Год журнала:
2022,
Номер
61(37)
Опубликована: Июль 12, 2022
Abstract
Simple
access
to
aryl
sulfinates
from
iodides
and
bromides
is
reported
using
an
inexpensive
Ni‐electrocatalytic
protocol.
The
reaction
exhibits
a
broad
scope,
uses
stock
solution
of
simple
SO
2
as
sulfur
source,
can
be
scaled
up
in
batch
recycle
flow
settings.
limitations
this
are
clearly
shown
put
into
context
by
benchmarking
with
state‐of‐the‐art
Pd‐based
methods.
Organic Chemistry Frontiers,
Год журнала:
2024,
Номер
11(9), С. 2638 - 2664
Опубликована: Янв. 1, 2024
This
review
describes
the
recent
advances
in
different
reaction
types
and
catalytic
systems
for
construction
of
C–NAr
S–NAr
bonds
by
nitroaromatic
reductive
cross-coupling.
ACS Catalysis,
Год журнала:
2024,
Номер
14(7), С. 5227 - 5235
Опубликована: Март 21, 2024
Sulfonamides
are
prominently
featured
in
organic
synthesis
and
medicinal
chemistry.
Yet,
a
general
synthetic
platform
for
the
modular
construction
of
aryl
sulfonamides
remains
elusive.
Herein,
metal-free
photoredox-catalyzed
three-component
via
an
sulfonyl
ammonium
salt
intermediate,
which
was
generated
situ
SET
event,
has
been
established.
A
variety
structurally
diverse
primary,
secondary,
tertiary
were
synthesized
rapidly
from
abundant
amines
or
sodium
azide
under
mild
conditions.
Notably,
primary
aliphatic
amine,
challenging
Cu-catalyzed
protocols,
worked
well
this
approach.
Moreover,
fluoride
can
be
accessed
smoothly
as
well,
using
potassium
hydrogen
nucleophile.
The
potential
utility
conversion
is
demonstrated
facile
three
bioactive
drug
compounds.
Preliminary
mechanistic
studies
have
revealed
that
radical
key
intermediates
mechanistically
innovative
methodology.
