Angewandte Chemie,
Journal Year:
2024,
Volume and Issue:
136(32)
Published: May 23, 2024
Abstract
Development
of
chiral
indenyl
ligands
for
asymmetric
C−H
activation
is
a
longstanding
challenge,
and
extremely
few
successes
have
been
achieved.
In
this
paper,
we
describe
class
readily
accessible,
facilely
tunable
user‐friendly
featuring
[2.2]benzoindenophane
skeleton
via
divergent
synthesis
strategy.
The
corresponding
rhodium
catalysts
were
successfully
applied
in
the
reaction
O‐Boc
hydroxybenzamide
with
alkenes
to
give
various
dihydroisoquinolone
products
(up
97
%
yield,
up
98
ee).
Moreover,
carboxylic
acids
alkynes
was
also
accomplished,
providing
range
axially
isocoumarins
99
94
Notably,
represents
first
example
enantioselective
transition
metal
catalyzed
C(sp
2
)−H
activation/oxidative
coupling
benzoic
internal
construct
isocoumarins.
Given
many
attractive
features
ligands,
such
as
convenient
synthesis,
high
tunability
exclusive
face‐selectivity
coordination,
its
applications
more
catalytic
other
catalysis
are
foreseen.
European Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
26(27)
Published: June 8, 2023
Abstract
Heterocyclics
are
the
crucial
scaffolds
present
in
pharmaceuticals,
natural
products,
biologically
active
compounds
and
agrochemicals.
Consequently,
development
of
simple
practical
methods
for
constructing
heterocyclics
has
always
been
a
fascinating
field
organic
synthesis.
Recently,
2‐acylbenzoic
acids,
highly
reactive
versatile
synthons,
have
broadly
applied
construction
heterocycles
due
to
their
multiple
reaction
sites.
In
this
review,
we
summarized
recent
progress
application
acids
synthesis
including
phthalides,
isochromanones,
isoindolines,
phthalazinones,
quinolones.
The
substrate
scopes,
proposed
mechanisms,
product
different
types
reactions
discussed.
Angewandte Chemie International Edition,
Journal Year:
2024,
Volume and Issue:
63(32)
Published: May 23, 2024
Abstract
Development
of
chiral
indenyl
ligands
for
asymmetric
C−H
activation
is
a
longstanding
challenge,
and
extremely
few
successes
have
been
achieved.
In
this
paper,
we
describe
class
readily
accessible,
facilely
tunable
user‐friendly
featuring
[2.2]benzoindenophane
skeleton
via
divergent
synthesis
strategy.
The
corresponding
rhodium
catalysts
were
successfully
applied
in
the
reaction
O‐Boc
hydroxybenzamide
with
alkenes
to
give
various
dihydroisoquinolone
products
(up
97
%
yield,
up
98
ee).
Moreover,
carboxylic
acids
alkynes
was
also
accomplished,
providing
range
axially
isocoumarins
99
94
Notably,
represents
first
example
enantioselective
transition
metal
catalyzed
C(sp
2
)−H
activation/oxidative
coupling
benzoic
internal
construct
isocoumarins.
Given
many
attractive
features
ligands,
such
as
convenient
synthesis,
high
tunability
exclusive
face‐selectivity
coordination,
its
applications
more
catalytic
other
catalysis
are
foreseen.
Advanced Synthesis & Catalysis,
Journal Year:
2024,
Volume and Issue:
366(3), P. 533 - 540
Published: Jan. 16, 2024
Abstract
Herein,
we
describe
metal‐free
fluorocyclization
of
2‐alkynylbenzoates
by
N
‐fluoropyridinium
salts.
The
present
method
allows
the
selective
synthesis
4‐fluoroisocoumarins
and
3,4,4‐trifluoroisochromanones
minor
modification
reaction
conditions.
The Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
88(13), P. 9360 - 9371
Published: June 16, 2023
A
novel
rhodium-catalyzed
tandem
C–H
annulation
of
commercially
available
benzaldehydes
and
aminobenzoic
acids
with
2
equiv
alkyne
is
reported
for
the
construction
isocoumarin-conjugated
isoquinolinium
salts
that
demonstrate
diverse
outstanding
photoactivity.
Depending
on
substituents
in
moiety,
they
display
either
highly
efficient
fluorescence
(up
to
99%
quantum
yield)
or
strong
quenching,
which
provided
by
transfer
HOMO
from
isocoumarin
moiety.
Importantly,
functional
groups
benzaldehyde
coupling
partner
also
strongly
affect
reaction
selectivity,
shifting
pathway
formation
photoinactive
isocoumarin-substituted
indenone
imines
indenyl
amines.
Selective
latter
can
be
achieved
using
a
reduced
amount
oxidizing
additive.
Molecules,
Journal Year:
2024,
Volume and Issue:
29(11), P. 2449 - 2449
Published: May 23, 2024
A
novel
metal-free
synthesis
of
3-substituted
isocoumarins
through
a
sequential
O-acylation/Wittig
reaction
has
been
established.
The
readily
accessible
(2-carboxybenzyl)-triphenylphosphonium
bromide
and
diverse
chlorides
produced
various
1H-isochromen-1-one
in
the
presence
triethylamine,
employing
O-acylation
an
intramolecular
Wittig
acid
anhydride.
Reactions
using
these
facile
conditions
have
exhibited
high
functional
group
tolerance
excellent
yields
(up
to
90%).
Moreover,
fluorescence
properties
isocoumarin
derivatives
were
evaluated
at
theoretical
experimental
levels
determine
their
potential
application
fluorescent
materials.
These
good
photoluminescence
THF
with
large
Stokes
shift
absolute
quantum
yield
up
14%.
