The Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
88(6), P. 3626 - 3635
Published: Feb. 27, 2023
Rh(III)-catalyzed
synthesis
of
benzoisothiazole
spiropyrrolidinediones
using
sulfoximine
as
a
directing
group
under
C–H
activation
and
[4
+
1]
annulation
strategy
with
maleimides
coupling
partner
is
reported.
The
cyclization
reaction
was
compatible
various
substituted
maleimides.
deuterium-labeling
studies
were
performed
to
investigate
the
mechanism
reaction.
Angewandte Chemie International Edition,
Journal Year:
2024,
Volume and Issue:
63(15)
Published: Jan. 30, 2024
Abstract
The
combination
of
achiral
Cp*Rh(III)
with
chiral
carboxylic
acids
(CCAs)
represents
an
efficient
catalytic
system
in
transition
metal‐catalyzed
enantioselective
C−H
activation.
However,
this
hybrid
catalysis
is
limited
to
redox‐neutral
activation
reactions
and
the
adopt
oxidative
remains
elusive
pose
a
significant
challenge.
Herein,
we
describe
development
electrochemical
Cp*Rh(III)‐catalyzed
annulation
sulfoximines
alkynes
enabled
by
acid
(CCA)
operationally
friendly
undivided
cell
at
room
temperature.
A
broad
range
enantioenriched
1,2‐benzothiazines
are
obtained
high
yields
excellent
enantioselectivities
(up
99
%
yield
98
:
2
er).
practicality
method
demonstrated
scale‐up
reaction
batch
reactor
external
circulation.
crucial
intermediate
isolated,
characterized,
transformed,
providing
rational
support
for
Rh(III)/Rh(I)
electrocatalytic
cycle.
New Journal of Chemistry,
Journal Year:
2024,
Volume and Issue:
48(6), P. 2576 - 2583
Published: Jan. 1, 2024
An
electrochemical
method
for
thioetherification
of
NH-sulfoximines
with
disulfides
is
reported.
The
utilization
electrochemistry
facilitating
these
reactions
eliminates
the
necessity
external
oxidants,
bases,
and
metal
catalysts.
Chemistry - A European Journal,
Journal Year:
2022,
Volume and Issue:
29(7)
Published: Oct. 27, 2022
The
p-Cymene
ruthenium(II)
complex
is
one
of
the
most
widely
used
catalysts
in
C-H
activation.
However,
enantioselective
activation
promoted
by
arene
complexes
has
not
been
realized
until
recently.
revealed
strategies
include
intramolecular
nitrene
insertion,
use
chiral
transient
directing
groups,
carboxylic
acid,
relay
catalysis,
and
ligands.
In
this
minireview,
these
advances
are
summarized
discussed
hope
spurring
further
developments.
Angewandte Chemie International Edition,
Journal Year:
2023,
Volume and Issue:
62(29)
Published: May 17, 2023
Sulfondiimines
are
diaza-analogues
of
sulfones
with
a
chiral
sulfur
center.
Compared
to
and
sulfoximines,
their
synthesis
transformations
have
so
far
been
studied
lesser
extent.
Here,
we
report
the
enantioselective
1,2-benzothiazine
1-imines,
i.e.,
cyclic
sulfondiimine
derivatives
from
sulfondiimines
sulfoxonium
ylides
via
C-H
alkylation/cyclization
reactions.
The
combination
[Ru(p-cymene)Cl2
]2
newly
developed
spiro
carboxylic
acid
is
key
achieving
high
enantioselectivity.
Organic Letters,
Journal Year:
2023,
Volume and Issue:
25(42), P. 7656 - 7660
Published: Oct. 12, 2023
A
novel
copper-catalyzed
cross-coupling
reaction
of
sulfinamides
and
aryl
boronic
acids
is
developed.
The
highly
chemoselective
stereospecific,
which
allows
mild
synthesis
optically
pure
sulfoximines
with
broad
scope
functional
group
tolerance.
utility
this
method
demonstrated
by
the
asymmetric
pharmaceutical
intermediates.
Molecules,
Journal Year:
2023,
Volume and Issue:
28(3), P. 1367 - 1367
Published: Feb. 1, 2023
Sulfoximines,
a
ubiquitous
class
of
structural
motifs,
are
widely
present
in
bioactive
molecules
and
functional
materials
that
have
received
considerable
attention
from
modern
organic
chemistry,
pharmaceutical
industries,
science.
Sulfoximines
proved
to
be
an
effective
directing
group
for
C-H
functionalization
which
was
investigated
the
synthesis
cyclic
sulfoximines.
Within
last
decade,
great
progress
has
been
achieved
Thus,
this
review
highlights
recent
advances
sulfoximines
via
activation
strategy
is
classified
based
on
substrate
types.
Angewandte Chemie International Edition,
Journal Year:
2024,
Volume and Issue:
63(31)
Published: April 29, 2024
Abstract
Given
the
tremendous
success
of
(p‐cymene)Ru
II
‐catalyzed
C−H
activation
over
past
20
years,
community
has
long
been
aware
that
development
chiral
η
6
‐benzene
(Ben)
ligands
should
be
a
potent
strategy
for
achieving
attractive
but
incredibly
underdeveloped
ruthenium(II)‐catalyzed
asymmetric
activation.
However,
it
rarely
achieved
due
to
severe
difficulty
in
developing
proper
Ben
ligands.
In
particular,
designing
by
connecting
benzene
fragment
framework
including
rings
remained
an
unsolved
challenge
until
this
effort.
Here
we
present
novel
class
axially
derived
from
readily
available
(
S
)‐5,5′,6,6′,7,7′,8,8′‐octahydro‐1,1′‐bi‐2‐naphthol
((
)‐H
8
‐BINOL)
4–8
steps.
Notably,
when
coordinated
with
ruthenium,
such
ligand
containing
three
only
forms
one
possible
isomeric
BenRu
complexes.
The
related
catalysts
could
effectively
catalyze
N‐sulfonyl
ketimines
alkynes,
affording
range
spirocyclic
sultams
up
99
%
yield
>99
ee.
These
are
expected
find
broad
applications
future.
Angewandte Chemie International Edition,
Journal Year:
2023,
Volume and Issue:
63(6)
Published: Dec. 16, 2023
Abstract
A
versatile
and
readily
available
chiral
amide
directing
group
has
been
developed
for
the
ruthenium(II)‐catalyzed
asymmetric
C−H
activation.
Asymmetric
activation
of
related
benzamides
with
various
olefins,
aldehydes
propargylic
alcohols
accomplished
high
stereoselectivities,
affording
a
series
products
including
3,4‐dihydroisocoumarins
(up
to
96
%
ee),
isocoumarins
92
phthalides
99
bicyclo[2.2.1]heptanes
(>20
:
1
dr),
4‐alkylidene‐3,4‐dihydroisocoumarins
97
ee)
allenes
dr).
Importantly,
our
methodologies
enabled
concise
syntheses
many
biologically
active
compounds
natural
(e.g.,
Montroumarin,
Cyclosporone
E,
Q,
Concentricolide,
Chuangxinol,
Eleutherol).
