Angewandte Chemie,
Journal Year:
2022,
Volume and Issue:
135(3)
Published: Nov. 16, 2022
Abstract
Satoh–Miura
reaction
is
an
important
method
for
extending
π‐systems
by
forging
multi‐substituted
benzene
rings
via
double
aryl
C−H
activation
and
annulation
with
alkynes.
However,
the
development
of
highly
enantioselective
remains
rather
challenging.
Herein,
we
report
asymmetric
between
1‐aryl
benzo[
h
]isoquinolines
internal
alkynes
enabled
a
SCpRh‐catalyst.
Judiciously
choosing
counteranion
Rh‐catalyst
crucial
desired
reactivity
over
competitive
formation
azoniahelicenes.
Detailed
mechanistic
studies
support
proposal
counteranion‐directed
switching
pathways
in
Rh‐catalyzed
activation.
Chemical Communications,
Journal Year:
2023,
Volume and Issue:
59(27), P. 4036 - 4039
Published: Jan. 1, 2023
The
synthesis
of
N-naphthyl
pyrazoles
has
been
realized
by
the
direct
three-component
reactions
enaminones,
aryl
hydrazine
hydrochlorides
and
internal
alkynes
via
Rh(III)
catalysis.
synthetic
employing
simple
substrates
lead
to
simultaneous
construction
dual
cyclic
moieties,
including
a
pyrazole
ring
phenyl
ring,
sequential
formation
two
C-N
three
C-C
bonds.
Angewandte Chemie International Edition,
Journal Year:
2022,
Volume and Issue:
62(3)
Published: Nov. 16, 2022
Satoh-Miura
reaction
is
an
important
method
for
extending
π-systems
by
forging
multi-substituted
benzene
rings
via
double
aryl
C-H
activation
and
annulation
with
alkynes.
However,
the
development
of
highly
enantioselective
remains
rather
challenging.
Herein,
we
report
asymmetric
between
1-aryl
benzo[h]isoquinolines
internal
alkynes
enabled
a
SCpRh-catalyst.
Judiciously
choosing
counteranion
Rh-catalyst
crucial
desired
reactivity
over
competitive
formation
azoniahelicenes.
Detailed
mechanistic
studies
support
proposal
counteranion-directed
switching
pathways
in
Rh-catalyzed
activation.
Organic Letters,
Journal Year:
2022,
Volume and Issue:
24(46), P. 8470 - 8475
Published: Nov. 14, 2022
A
rhodium(III)-catalyzed
Satoh-Miura
type
oxidative
annulation
of
N-aryl
2-pyridone
derivatives
is
described
using
internal
alkyne
as
a
coupling
partner.
weakly
coordinating
carbonyl
group
the
ring
utilized
for
this
transformation.
The
reaction
proceeds
with
broad
scope
and
wide
functional
tolerance.
solvent
plays
an
important
role
in
developed
method
to
furnish
different
class
annulated
product.
preliminary
investigation
was
carried
out
explore
photophysical
properties
obtained
polyarylated
N-naphthyl
2-pyridones.
Organic Letters,
Journal Year:
2023,
Volume and Issue:
25(11), P. 1952 - 1957
Published: March 10, 2023
A
Pd(II)-catalyzed
straightforward
oxidative
naphthylation
of
unmasked
2-pyridone
derivatives
is
described
using
a
twofold
internal
alkyne
as
coupling
partner.
The
reaction
proceeds
through
N–H/C–H
activation
to
provide
polyarylated
N-naphthyl
2-pyridones.
An
unusual
annulation
at
the
arene
C–H
bond
diarylalkyne
leads
formation
2-pyridones,
where
2-pyridone-attached
phenyl
ring
naphthyl
polyaryl-substituted.
Mechanistic
studies
and
DFT
calculations
suggest
plausible
mechanism
based
on
activation.
were
studied
explore
encouraging
photophysical
properties.
Organic Letters,
Journal Year:
2023,
Volume and Issue:
25(4), P. 703 - 707
Published: Jan. 23, 2023
We
report
a
novel
rhodium-catalyzed
rearrangement
involving
N-substituted
2-thiopyridones
and
diazoesters.
This
reaction
proceeds
through
the
formation
of
sulfur
ylides,
followed
by
direct
C-N
bond
cleavage
to
achieve
N-to-C
1,4-pyridyl
migration.
The
protocol
can
be
used
construct
various
thiopyridines
possessing
tetrasubstituted
carbon
stereocenters
in
moderate
excellent
yields,
which
expands
transformation
pattern
ylide
intermediates
reactions.
Organic Letters,
Journal Year:
2023,
Volume and Issue:
25(31), P. 5779 - 5783
Published: July 27, 2023
Herein,
a
ruthenium-mediated
remote
C-H
mono-
and
disulfonylation
of
2-pyridones
with
arylsulfonyl
chlorides
is
developed.
The
catalytic
system
consisting
[Ru(p-cymene)Cl2]2
catalyst
KOAc
additive
allows
to
undergo
C3,C5-disulfonylation
in
1,4-dioxane,
C5-sulfonylation
when
the
C3-position
blocked.
successful
transformation
products
late-stage
modification
estrone
further
highlighted
potential
utility
significance
this
synthetic
protocol.
Preliminary
mechanistic
studies
indicated
that
regioselectivity
might
be
dictated
via
chelation-assisted
ruthenation.
Advanced Synthesis & Catalysis,
Journal Year:
2023,
Volume and Issue:
365(7), P. 1027 - 1035
Published: March 16, 2023
Abstract
Rh(III)‐catalyzed
chelation‐assisted
C8‐selective
C−H
alkenylation
and
alkylation
of
1,2,3,4‐tretrahydroquinolines
with
styrenes
allylic
alcohols
have
been
realized.
The
cationic
Rh(III)
catalytic
system
in
combination
a
amount
copper
acetate
uses
oxygen
as
the
terminal
oxidant
catalyzes
stereoselective
C8‐alkenylation
1,2,3,4‐tetrahydroquinolines
to
give
corresponding
products
56–93%
yields
wide
substrate
scope
broad
functional
group
compatibility.
reaction
can
be
scaled
up.
Moreover,
this
protocol
extended
C8‐alkylation
alcohols,
providing
access
various
8‐(3‐oxoalkyl)‐1,2,3,4‐tetrahydroquinolines
77–90%
yields.
selection
N‐directing
is
essential
for
catalysis,
readily
installable
removable
N‐(2‐pyrimidyl)
proves
optimal
choice.
Preliminary
mechanistic
studies
are
performed
gain
insights
into
mechanism.
magnified
image
