Organic Chemistry Frontiers,
Год журнала:
2023,
Номер
10(5), С. 1322 - 1345
Опубликована: Янв. 1, 2023
Functionalization
of
alkenes/alkynes
is
a
highly
effective
route
to
achieve
molecular
complexity.
This
review
summarizes
recent
progresses
on
the
1,2-difunctionalization/hydrofunctionalization
unactivated
with
C−S
bond
formation.
European Journal of Organic Chemistry,
Год журнала:
2023,
Номер
26(12)
Опубликована: Фев. 15, 2023
Abstract
This
review
provides
an
overview
of
the
use
aryldiazonium
salts
as
source
aryl
radicals
and
their
application
in
development
selective
transformations
over
last
13
years.
Examples
were
organized
under
thermal
photocatalytic
transformations.
accessible
follow‐up
this
field
for
both
radical
catalytic
chemists
working
industry
well
academia.
Angewandte Chemie International Edition,
Год журнала:
2024,
Номер
63(11)
Опубликована: Янв. 26, 2024
Abstract
In
contrast
with
the
well‐established
C(sp
2
)−SCF
3
cross‐coupling
to
forge
Ar−SCF
bond,
corresponding
enantioselective
coupling
of
readily
available
alkyl
electrophiles
chiral
bond
has
remained
largely
unexplored.
We
herein
disclose
a
copper‐catalyzed
radical
range
secondary/tertiary
benzyl
radicals
easily
(Me
4
N)SCF
reagent.
The
key
success
lies
in
utilization
phosphino‐oxazoline‐derived
anionic
N,N,P‐ligands
through
tuning
electronic
and
steric
effects
for
simultaneous
control
reaction
initiation
enantioselectivity.
This
strategy
can
successfully
realize
two
types
asymmetric
reactions,
including
enantioconvergent
racemic
halides
three‐component
1,2‐carbotrifluoromethylthiolation
arylated
alkenes
under
mild
conditions.
It
therefore
provides
highly
flexible
platform
rapid
assembly
an
array
enantioenriched
SCF
‐containing
molecules
interest
organic
synthesis
medicinal
chemistry.
ACS Catalysis,
Год журнала:
2022,
Номер
12(17), С. 10764 - 10770
Опубликована: Авг. 18, 2022
A
copper-catalyzed
four-component
enantioselective
arylsulfonylcyanation
of
vinylarenes
has
been
developed
that
enables
easy
access
to
a
variety
chiral
β-sulfonyl
nitriles
with
up
95%
yield
and
96%
ee.
The
reaction
utilizes
bench-stable
SO2
surrogate
(SOgen),
takes
place
under
mild
conditions,
exhibits
good
substrate
scope
functional
group
compatibility.
Control
experiments
show
the
use
SOgen
as
is
key
achieving
excellent
reactivities
enantioselectivities.
Preliminary
mechanistic
data
indicates
this
vinylarene
1,2-difunctionalization
likely
proceeds
by
radical
pathway.
exemplifies
rare
case
catalysis
involving
gaseous
SO2.
European Journal of Organic Chemistry,
Год журнала:
2023,
Номер
26(25)
Опубликована: Апрель 25, 2023
Abstract
Compounds
containing
sulfonyl‐derived
functional
groups
have
received
intensive
attention
owing
to
their
widespread
applications
in
life
science,
pharmaceuticals
and
materials
science.
To
access
this
type
of
compounds,
the
multi‐component
sulfonylation
reactions
relying
on
sulfur
dioxide
(SO
2
)
insertion
strategy
emerged
as
novel
attractive
approaches
past
decade.
The
utilization
SO
surrogates
for
multicomponent
(MCRs)
improved
reaction
flexibility
step
economy.
Moreover,
some
advances
been
achieved
challenging
but
practical
asymmetric
MCRs
construction
high
value‐added
chiral
sulfones.
This
review
aims
summarize
progress
made
involving
from
2019
2022,
point
out
potentials
challenges
field.
Organic Chemistry Frontiers,
Год журнала:
2023,
Номер
10(19), С. 4972 - 5027
Опубликована: Янв. 1, 2023
This
review
comprehensively
summarizes
the
dichalcogenative
functionalization
of
unsaturated
compounds
over
past
decade.
The
scopes,
limitations
and
detailed
reaction
mechanisms
are
also
discussed.
Organic Chemistry Frontiers,
Год журнала:
2023,
Номер
10(5), С. 1224 - 1229
Опубликована: Янв. 1, 2023
Brønsted
base
catalyzed
thiosulfonylation
and
trifluoromethylthiosulfonylation
of
ynones
produced
thio-functionalized
vinyl
sulfones
in
high
yields
with
excellent
E
-selectivity.
Organic Letters,
Год журнала:
2023,
Номер
25(31), С. 5916 - 5921
Опубликована: Июль 27, 2023
A
copper-catalyzed
trifluoromethylthio-arylsulfonylation
between
1,3-enynes,
AgSCF3,
aryldiazonium
tetrafluoroborates,
and
SO2
(from
SOgen)
is
presented,
which
could
introduce
sulfone,
SCF3,
allene
moieties
into
one
molecule
simultaneously.
This
strategy
features
mild
reaction
conditions,
good
substrate
compatibility,
excellent
regioselectivity.
The
products
obtained
have
the
potential
for
further
conversion
other
valuable
compounds.
Initial
investigations
mechanism
suggest
that
it
may
proceed
via
a
radical
pathway.
Notably,
SOgen
was
proven
as
uniquely
effective
surrogate
in
this
transformation.
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.
Organic Chemistry Frontiers,
Год журнала:
2024,
Номер
11(6), С. 1678 - 1684
Опубликована: Янв. 1, 2024
This
method
allows
for
the
enantioselective
synthesis
of
β-azide
sulfones
via
iron-catalyzed
vicinal
azide-sulfonylation
acrylamides.
It
makes
first
instance
achieving
asymmetric
construction
through
iron
catalysis
with
SO
2
insertion.
