Angewandte Chemie,
Journal Year:
2023,
Volume and Issue:
135(46)
Published: Oct. 2, 2023
Abstract
This
research
explores
the
enantioselective
hydrosulfonylation
of
various
α,β‐unsaturated
carbonyl
compounds
via
use
visible
light
and
redox‐active
chiral
Ni‐catalysis,
facilitating
synthesis
enantioenriched
α‐chiral
sulfones
with
remarkable
enantioselectivity
(exceeding
99
%
ee).
A
significant
challenge
entails
enhancing
reactivity
between
metal‐coordinated
moderate
electrophilic
sulfonyl
radicals,
aiming
to
minimize
background
reactions.
The
success
our
approach
stems
from
two
distinctive
attributes:
1)
Cl‐atom
abstraction
employed
for
radical
generation
chlorides,
2)
single‐electron
reduction
produce
a
key
enolate
Ni‐complex.
latter
process
appears
enhance
feasibility
radical's
addition
electron‐rich
radical.
An
in‐depth
investigation
into
reaction
mechanism,
supported
by
both
experimental
observations
theoretical
analysis,
offers
insight
intricate
process.
Moreover,
versatility
methodology
is
highlighted
through
its
successful
application
in
late‐stage
functionalization
complex
bioactive
molecules,
demonstrating
practicality
as
strategy
producing
sulfones.
The Journal of Organic Chemistry,
Journal Year:
2025,
Volume and Issue:
unknown
Published: April 2, 2025
A
photoredox-catalyzed
radical
cascade
cyclization
of
N-(o-cyanobiaryl)acrylamides
with
sulfonyl
chlorides
for
the
construction
sulfonyl-containing
pyrido[4,3,2-gh]phenanthridines
has
been
disclosed.
The
developed
synthetic
tool
tolerates
a
broad
range
to
undergo
sequence,
including
addition,
nitrile
insertion,
and
cyclization.
Advanced Synthesis & Catalysis,
Journal Year:
2023,
Volume and Issue:
365(12), P. 1989 - 1994
Published: May 31, 2023
Abstract
An
oxidative
sulfonylation/cyclisation
of
N
‐propargylindoles
with
Hantzsch
esters
through
sulfur
dioxide
insertion
has
been
developed.
The
method
uses
Na
2
S
O
5
as
source
along
4‐alkyl‐substituted
radical
precursors
for
accessing
sulfonyl
radicals,
and
allows
the
synthesis
2‐sulfonated
9
H
‐pyrrolo[1,2‐
a
]indoles.
Organic Letters,
Journal Year:
2023,
Volume and Issue:
25(37), P. 6858 - 6862
Published: Sept. 13, 2023
Rh–(R,R)-f-spiroPhos
complex-catalyzed
asymmetric
hydrogenation
of
α-substituted
alkenyl
sulfones
has
been
achieved,
affording
the
chiral
γ-keto
and
simple
α-alkyl-substituted
in
high
yields
(96–99%)
with
excellent
chemo-/enantioselectivities
(86–96%
ee)
turnover
numbers
(TONs)
up
to
4000.
The
method
provides
an
efficient
high-enantioselectivity
strategy
for
under
mild
conditions.
Moreover,
obtained
product
was
transformed
into
other
important
sulfones.
Organic Chemistry Frontiers,
Journal Year:
2023,
Volume and Issue:
10(16), P. 3995 - 4001
Published: Jan. 1, 2023
An
alkoxycarbonyl-radical-triggered
cascade
cyclization
reaction
of
N
-(
o
-cyanobiaryl)acrylamides
with
alkyloxalyl
chlorides
is
developed,
leading
to
diverse
ester-containing
phenanthridines.
Asian Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
12(10)
Published: Aug. 23, 2023
Abstract
In
the
last
two
decades,
chiral
hydrogen
bonding
catalysis
has
been
enormously
utilized
to
trigger
several
valuable
synthetic
transformations.
Similarly,
modern
day
radical
chemistry
witnessed
potency
of
visible
light
photoredox
generate
radicals
via
single
electron
transfer
pathway.
Recently,
their
cooperative
effect
proved
be
a
key
strategy
access
many
elegant
transformations
that
are
only
feasible
under
synergistic
action
these
catalytic
systems.
This
dual
system
demonstrates
high
efficiency
for
introducing
molecular
complexity
in
an
enantioselective
fashion.
this
mini
review,
we
have
compiled
most
recent
development
surfaced
three
years
with
particular
attention
paid
mechanistic
details
and
its
substrate
scope.
We
hope
review
will
provide
readers
brief
overview
advancement
application
catalysts
bond
donors
reactions.
Advanced Synthesis & Catalysis,
Journal Year:
2023,
Volume and Issue:
366(3), P. 488 - 493
Published: Dec. 23, 2023
Abstract
A
four‐component
reaction
of
N
‐arylpropiolamides,
Hantzsch
esters,
Na
2
S
O
5
and
water
via
a
radical
cascade
cyclization
process
with
the
insertion
sulfur
dioxide
mediated
by
K
8
is
reported.
series
alkylsulfonated
spiro[4,5]
trienones
are
prepared
up
to
86%
yield
good
functional
group
tolerance
substrate
applicability.
Preliminary
mechanism
experiments
indicate
that
carbonyl
oxygen
originated
from
water.
This
review
highlights
the
progress
achieved
in
transition-metal
(ruthenium,
rhodium,
iridium,
and
nickel)
catalyzed
asymmetric
hydrogenation
of
unsaturated
sulfones
including
substrate
scopes,
catalytic
mechanisms,
applications.
