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.
Chemical Science,
Journal Year:
2023,
Volume and Issue:
14(40), P. 11267 - 11272
Published: Jan. 1, 2023
Herein,
we
report
the
first
palladium/MPAA
catalyzed
enantioselective
C-H
activation/[4
+
1]
annulation
of
diarylmethyltriflamide
and
olefins
to
construct
chiral
cis-1,3-disubstituted
isoindoline
derivatives.
The
use
a
readily
accessible
mono-N-protected
amino
acid
as
ligand
improves
efficiency
enantioselectivity
catalytic
transformation.
developed
method
provides
access
both
enantiomers
product
using
either
d
or
l-phenylalanine
derivative
facilitating
synthesis
optically
active
1,3-disubstituted
Organic Chemistry Frontiers,
Journal Year:
2023,
Volume and Issue:
10(23), P. 5916 - 5922
Published: Jan. 1, 2023
Rh(
iii
)-catalyzed
redox-neutral
C–H
[4
+
1]
annulation
of
sulfoximines
with
α,α-difluoromethylene
alkynes
has
been
realized
to
diastereoselectively
build
E
-monofluoroalkenyl
benzoisothiazole
1-oxides.
Angewandte Chemie International Edition,
Journal Year:
2023,
Volume and Issue:
63(5)
Published: Dec. 13, 2023
Abstract
Sulfoxides
are
widely
used
in
the
pharmaceutical
industry
and
as
ligands
asymmetric
catalysis.
However,
efficient
synthesis
of
this
structural
motif
remains
limited.
In
study,
we
disclosed
a
Ni‐catalyzed
enantioconvergent
reaction
that
utilizes
both
racemic
allenyl
carbonates
β‐sulfinyl
esters.
Our
method
employs
cheap
more
sustainable
Ni(II)
precatalyst
successfully
overcomes
challenging
poisoning
effect
instability
sulfenate
generated
situ.
This
enables
series
dienyl
sulfoxides
with
enantioselectivity
up
to
98
%
ee.
The
product
exhibits
tremendous
potential
various
applications,
including
diastereoselective
Diels–Alder
reactions,
coordination
transition
metals,
incorporation
into
medicinal
compounds,
among
others.
Using
combination
experimental
computational
methods,
have
uncovered
an
interesting
associated
outersphere
mechanism
contrasts
conventional
mechanisms
commonly
observed
metal
The Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
88(4), P. 2322 - 2333
Published: Jan. 26, 2023
An
efficient
and
practical
SO2
insertion
protocol
of
NH-sulfoximines
with
aryldiazonium
tetrafluoroborates
DABSO
toward
N-sulfonyl
sulfoximines
has
been
developed
under
mildly
basic
conditions.
This
transformation
features
easy
operation,
readily
available
substrates,
mild
A
tentative
mechanism
is
proposed,
which
indicates
that
the
would
be
radical
donors
standard
reaction
The
aryl
produced
in
situ
from
diazonium
salts
trapped
by
to
generate
an
arylsulfonyl
then
undergo
further
final
sulfoximines.
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.
