Angewandte Chemie,
Journal Year:
2022,
Volume and Issue:
135(12)
Published: Dec. 30, 2022
Abstract
The
C−H
functionalization
strategy
provides
access
to
valuable
molecules
that
previously
required
convoluted
synthetic
attempts.
Dual
unsymmetrical
functionalization,
with
a
single
bifunctional
reagent,
is
an
effective
tactic.
Propargyl
alcohols
(PAs),
despite
containing
reactive
C≡C
bond,
have
not
been
explored
as
building
blocks
via
oxidative
cleavage.
Annulations
activation
are
versatile
and
synthetically
attractive
strategy.
We
disclose
PA
new
reagent
for
dual
of
biphenylamine
regioselectively
annulated
outcomes.
On
tuning
the
conditions,
annulation
bifurcated
towards
unusual
cyclization.
This
method
accommodates
wide
range
PAs
showcases
late‐stage
diversification
some
natural
products.
Advanced Synthesis & Catalysis,
Journal Year:
2023,
Volume and Issue:
365(11), P. 1770 - 1776
Published: March 21, 2023
Abstract
Rh‐catalyzed
C−H
activation
of
arenes
for
oxidative
annulations
with
alkynes
stands
out
as
a
protocol
polycyclic
scaffolds.
This
perspective
drives
us
to
disclose
herein
rhodium
catalyzed
regioselective
triple
annulation
enaminones
hydroxyl‐alkynoates
via
double
functionalization
naphtho‐pyran
Secondary
coordination
OH
in
alkynoate
dictated
the
regioselectivity.
Initial
lactonization
occurred
chemoselectively
on
enamine
part
carbo
rhodation
followed
by
reductive
elimination.
was
scalable
and
has
shown
high
functionality
tolerance.
KIE
studies
were
done
get
insight
mechanism,
some
downstream
transformations
achieved
show
synthetic
potential
method.
Organic Letters,
Journal Year:
2022,
Volume and Issue:
24(28), P. 5062 - 5067
Published: July 11, 2022
We
disclose
herein
a
Rh(III)-catalyzed
migratory
three-point
double
annulation
of
o-alkenyl
phenols
with
propargyl
alcohols
for
de
novo
construction
naphtho
furan
derivatives
in
regio-
and
chemoselective
manner.
The
protocol
orchestrates
two
new
rings
four
bonds
one
operation
without
the
need
any
additive.
Necessary
labeled
control
experiments
are
conducted
to
elucidate
reaction
mechanism.
A
tertiary
hydroxyl
group
is
found
be
crucial
both
controlling
regioselective
insertion
alkyne
through
chelation
rhodium
form
key
spiro
cyclic
intermediate
forcing
ring
expansion
via
unusual
selective
olefin
reshuffling,
apart
from
forming
an
extra
(furan)
ring.
scalable
shows
tolerance
late
stage
functionalization
natural
products.
Angewandte Chemie International Edition,
Journal Year:
2022,
Volume and Issue:
62(12)
Published: Dec. 30, 2022
The
C-H
functionalization
strategy
provides
access
to
valuable
molecules
that
previously
required
convoluted
synthetic
attempts.
Dual
unsymmetrical
functionalization,
with
a
single
bifunctional
reagent,
is
an
effective
tactic.
Propargyl
alcohols
(PAs),
despite
containing
reactive
C≡C
bond,
have
not
been
explored
as
building
blocks
via
oxidative
cleavage.
Annulations
activation
are
versatile
and
synthetically
attractive
strategy.
We
disclose
PA
new
reagent
for
dual
of
biphenylamine
regioselectively
annulated
outcomes.
On
tuning
the
conditions,
annulation
bifurcated
towards
unusual
cyclization.
This
method
accommodates
wide
range
PAs
showcases
late-stage
diversification
some
natural
products.
Organic Letters,
Journal Year:
2023,
Volume and Issue:
25(16), P. 2923 - 2927
Published: April 17, 2023
An
efficient
approach
for
the
synthesis
of
N-substituted
indenoisoquinolinones
via
rhodium(III)-catalyzed
C-H
bond
activation/subsequent
[4
+
2]
cyclization
starting
from
easily
available
2-phenyloxazolines
and
2-diazo-1,3-indandiones
has
been
developed.
A
series
indeno[1,2-c]isoquinolinones
were
obtained
in
up
to
93%
yield
through
functionalization,
followed
by
intramolecular
annulation,
elimination,
ring-opening
a
"one
pot
manner"
under
mild
reaction
conditions.
This
protocol
features
excellent
atom-
step-economy
provides
novel
strategy
chance
study
their
biological
activities.
Organic & Biomolecular Chemistry,
Journal Year:
2023,
Volume and Issue:
21(29), P. 5985 - 5989
Published: Jan. 1, 2023
A
convenient
method
for
the
alkylation
of
3-arylbenzo[d]isoxazoles
with
maleimides
under
redox-neutral
conditions
has
been
developed,
giving
a
series
substituted
succinimides
in
up
to
99%
yield.
This
transformation
is
highly
selective
give
succinimides,
and
Heck-type
products
are
successfully
avoided.
protocol
features
100%
atom-economy
broad
substrate
tolerance,
provides
novel
strategy
synthesis
diverse
an
opportunity
succinylation
protein
medication
pharmacologists
discover
first-in-class
drugs.
Organic Chemistry Frontiers,
Journal Year:
2022,
Volume and Issue:
9(20), P. 5617 - 5623
Published: Jan. 1, 2022
A
method
for
the
synthesis
of
6-alkenylindazolo[3,2-a]isoquinolines
via
Rh(
iii
)-catalysed
C–H
bond
activation/cyclization
has
been
developed.
The
title
products
exhibited
favourable
fluorescence
properties
which
were
verified
by
relevant
experiments.
Advanced Synthesis & Catalysis,
Journal Year:
2023,
Volume and Issue:
365(12), P. 2036 - 2042
Published: May 22, 2023
Abstract
Rh(III)‐catalyzed
cascade
oxidative
C−H
functionalization/
aza
‐annulation
of
indole
and
pyrrole
‐N
‐carboxamides
with
1,3‐enynes
involving
1,4‐rhodium
migration
is
disclosed.
This
[4+1]
annulation
protocol
provides
an
approach
for
the
synthesis
imidazo[1,5‐a]indol‐3(2
H
)‐ones
from
easily
accessible
substrates.
Moreover,
sulfonamides
are
also
found
to
be
well
compatible
in
this
method,
leading
corresponding
benzo[
d
]sultams.
The
efficacy
highlighted
by
handy
downstream
conversions
dienyl‐sultam.
The Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
89(8), P. 5589 - 5605
Published: April 5, 2024
Diversity-oriented
synthesis
strategy
for
the
efficient
assembly
of
indole-fused
polycyclic
scaffolds
via
rhodium-catalyzed
NH-indole-directed
C–H
coupling
with
propargylic
alcohol
derivatives
in
a
regioselective
manner
was
developed.
Five
2-phenyl-1H-indole-embedded
core
skeletons
were
synthesized.
In
particular,
three
different
exo-olefin-containing
polycycles
realized,
which
may
be
manipulated
further
chemistry.
The Journal of Organic Chemistry,
Journal Year:
2022,
Volume and Issue:
88(1), P. 143 - 153
Published: Dec. 23, 2022
An
efficient
method
of
Rh(III)-catalyzed
coupling
reaction
between
2-arylquinazolinones
and
gem-difluorostyrenes
has
been
developed.
In
this
work,
two
diverse
structures
monofluoroalkenes
isoindolo[1,2-b]quinazolin-10(12H)-one
derivatives
were
respectively
synthesized
by
controlling
the
amount
additives
(Ca(OH)2
AgNTf2)
to
achieve
controlled
stepwise
breaking
C-F
bonds
gem-difluorostyrenes.
This
characteristics
a
wide
range
substrates
good
functional
group
tolerance.
Meanwhile,
several
control
experiments
conducted
plausible
mechanism
was
proposed.
